Synthesis, Characterization of Two New Schiff Base and Their PdII Complexes and Investigation of Palladium Catalyzed Cross-Coupling Reactions

Synthesis, Characterization of Two New Schiff Base and Their PdII Complexes and Investigation of Palladium Catalyzed Cross-Coupling Reactions | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article Synthesis, Characterization of Two New Schiff Base and Their PdII Complexes and Investigation of Palladium Catalyzed Cross-Coupling Reactions Nevin Turan, Kenan Buldurun, Mustafa Bingöl, Naki Çolak This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-3913928/v1 This work is licensed under a CC BY 4.0 License Status: Posted Version 1 posted You are reading this latest preprint version Abstract Two Schiff base ligands, S 1 and S 2 , were synthesized from the reaction of 2-amino-5-ethyl-4-methylthiophene-3-carbonitrile with 2-hydroxybenzaldehyde and 4-nitrobenzaldehyde were investigated for their coordination to PdCl 2 (CH 3 CN) 2 . The prepared ligands S 1 and S 2 and the Pd II complexes 1 and 2 were characterized by using FTIR, 1 H, and 13 C NMR, UV-Vis, TGA, elemental analysis, molar conductivity, mass, and magnetic susceptibility. The characterization data agree well with the formulation of ligands S 1 and S 2 and complexes 1 and 2. The geometries of the metal chelate were discussed with the help of magnetic and spectroscopic measurements. Finally, the catalytic potential of the synthesized Pd II complexes for Suzuki-Miyaura and Mizoroki-Heck coupling reactions was investigated using GC-MS. As a result, it was observed that the palladium complexes are the active catalysts in suitable Suzuki-Miyaura and Mizoroki-Heck C-C coupling reactions. Schiff base ⸱ PdII complex ⸱ Characterization ⸱ Suzuki coupling ⸱ Heck coupling reactions Figures Figure 1 Figure 2 Figure 3 Figure 4 Introduction Palladium catalyzed cross-coupling reactions are considered to be powerful tools and important fields range in organic synthesis, natural products, and materials sciences (Heck 1985 ; Maluenda and Navarro 2015 ; Biricik et al. 2010). Palladium-catalyzed Suzuki-Miyaura C-C reactions between aryl halides and aryl boronic acids are a powerful tool in modern synthetic chemistry (Corbet and Mignani 2006 ). The reaction is usually catalyzed by palladium catalyst precursors, ligands binding to the palladium center and stabilizing the catalyst during the reaction process, and bases capturing the boronate group. Choosing the right ligands is crucial in determining how the reaction proceeds (Zhang et al. 2021). The Suzuki-Miyaura C-C reaction has the exceptional advantages of proven efficiency, compatibility with a wide range of functional groups, and mild reaction conditions. It is widely used in industrial synthesis and is the primary method for C-C bond formation for organic synthetic chemistry. The importance of palladium-catalyzed C-C bond formation reactions has led the chemical community to search for highly active and stable palladium-based catalysts, which should also be versatile and efficient systems (Beller et al. 2004 ; Yaşar et al. 2015 ). A powerful tool in organic synthesis for the formation of C-C bond is the palladium-catalyzed arylation or vinylation of olefins, also known as the Mizoroki-Heck reaction (Alonso et al. 2005 ; Montoya et al. 2008 ). A review of the literature shows that this reaction has been carried out using many phosphine-based palladium catalysts (Baysal et al. 2007 ; Amatore et al. 2014 ; Scott et al. 2021). The phosphine ligands are toxic, sensitive to air, expensive, and difficult to synthesize. To overcome these traditional disadvantages, the search has been on for the rational design of new catalysts for C-C bond formation reactions. Among the different metal catalysts, various ligand-palladium(0) or palladium(II) homogeneous complexes show an excellent performance as a catalyst in the Mizoroki-Heck coupling reaction (Buldurun et al. 2019 ;. Matsheku et al. 2021 ; Niakan et al. 2018 ). The influence of the Mizoroki-Heck coupling reaction in organic synthesis over the last few decades is also clearly demonstrated by the presence of publications on Mizoroki-Heck coupling reactions in the literature (Nagalakshmi et al. 2020 ; Gur’eva et al. 2019 ; Turan et al. 2022 ). Schiff bases are very common ligands in organometallic chemistry. Schiff bases coordinate to metal ions via the nitrogen atom of the azomethine (Yousif et al. 2017 ). Numerous industrial applications have arisen from the ease of synthesis of Schiff base ligands and the thermal and chemical stability of the resulting complexes. Schiff base-palladium(II) complexes appear to be active and suitable for the preparation of target compounds due to their ease of preparation and commercial availability (Billingsley and Buchwald 2007 ; Ingoglia et al. 2019 ). They have been widely used as catalysts in various organic reactions, such as olefinic polymerizations, olefinic hydrogenations, and toxic metal removal (Domin et al. 2005 ; Schmid et al. 2001 ; Talat et al. 2018 ). Schiff base complexes or frameworks have many applications in biochemistry, chemicals as catalysts, chemo-sensors, dyes and pigments, polymerization and fluorescence, organic lighting devices (Bondar et al. 2023 ; Paul and Barman 2024 ; Andrews et al. 2023 ; Nasaruddin et al. 2022 ). Thus, in continuation of our research interest in the synthesis, physicochemical and spectroscopic characterization, and catalytic applications of transition metal complexes we report here new Pd II complexes as an efficient catalyst in Suzuki-Miyaura and Mizoroki-Heck reactions. In this study, two new Schiff base ligands ( S 1 and S 2 ) and their Pd II metal complexes were synthesized and their structures were elucidated. Then the catalytic activities of the synthesized Pd II complexes (1 and 2) in Suzuki-Miyaura and Mizoroki-Heck coupling reactions were determined. The development of new palladium catalysts with high conversion, reaction rates, yields, and selectivity is in high demand on the market. Experimental Materials and instrumentation 2-hydroxybenzaldehyde, 4-nitrobenzaldehyde, glacial acetic acid, PdCl 2 (CH 3 CN) 2 , phenylboronic acid, styrene, CaCl 2 , KBr, KOH, NaOH, Na 2 CO 3 , K 2 CO 3 , KOBu t , Cs 2 CO 3 , MgSO 4 , CH 3 CN, ethyl alcohol, ethyl acetate, toluene, i -propanol, triethylamine, DCM, DMSO, DMF, dioxane, chloroform, acetone, methanol, hexane, water and diethyl ether were used as chemicals/reagents. All reagents and solvent used in study were purchased from Sigma-Aldrich and used without additional drying and purification. All of the synthesis was performed using the standard Schlenk tube technique in an inert gas atmosphere. The elemental analyses were carried out using a Thermos Scientific Flas 2000 CNSO analyzer. FT-IR spectra were recorded in the range 400–4000 cm − 1 on PerkinElmer Spectrum 65. 1 H and 13 C NMR spectra were performed using a Bruker UPB Avance-III 400 MHz NMR spectrometer. UV–Vis spectra were measurement as DMF solutions using a Shimadzu UV-1800 spectrophotometer. Magnetic susceptibility was performed using the Guoy method with Hg[(Co(SCN) 4 ] as calibrant on the Sherwood Auto Magnetic Susceptibility Balance. The C-C coupling products (recorded in the catalytic reactions) were analyzed used with GC-FID Chromatograph methods. Mass Spectrometer Agilent Technologies 6890N. The melting points were determined using an electro-thermal 9200 melting point apparatus. The conductivity of the Pd II complexes was measured with the Jenway 4010 conductivity meter in 10 − 3 M DMF. Synthesis and characterization of ( E )-4-ethyl-2-(2-hydroxybenzylideneamino)-5-methylthiophene-3-carbonitrile (S 1 ) and ( E )-4-ethyl-5-methyl-2-(4-nitrobenzylideneamino)thiophene-3-carbonitrile (S 2 ) The novel ligands S 1 and S 2 were prepared by reacting 2-amino-5-ethyl-4-methylthiophene-3-carbonitrile and 2-hydroxybenzaldehyde ( S 1 ) and 4-nitrobenzaldehyde ( S 2 ) in the presence of few drops of glacial acetic acid in 20 mL methanol solution for 3 h (characterization data were given in supplementary material). The resulting crude products were recrystallized in hot methanol. The synthesis scheme of the ligands S 1 and S 2 are given in Fig. 1 . S 1 : Yield: 85%. Yellow solid. M.p.: 150°C. Anal. Calc. for (C 15 H 14 N 2 OS): C, 66.64; H, 5.22; N, 10.36; S, 11.86. Found: C, 66.70; H, 5.20; N, 10.35; S, 11.84%. UV-Vis λmax, nm, (ε, M − 1 cm − 1 ): 204 (3614), 208 (3211), 215 (2576), 230 (2734), 290 (1807), 375 (3153), 385 (3284), 395 (3372). FT-IR ν, cm − 1 : 3449 (–OH), 3058 (Ar. –CH), 2967, 2933, 2872 (Alip. –CH), 2222 (CN), 1619 (CH = N), 1598, 1566, 1492 (Ar. C = C), 1166 (C–O), 761 (C–S–C). 1 H-NMR (400 MHz, CDCl 3 ) δ, ppm: 11.99 (s, 1H, –OH), 8.50 (s, H, CH = N), 7.41–6.95 (m, 4H, Ar. –CH), 2.64, 2.63 (q, 2H, CH 2 ), 2.39 (s, 3H, –CH 3 ), 1.22 (t, 3H, –CH 2 C H 3 ). 13 C-NMR (100 MHz, CDCl 3 ) δ, ppm: 161.23 (C7), 160.99 (C2), 156.59 (C8), 139.58-107.56 (C1-C6, C9-C11, C13), 20.88 (C17), 14.37–13.36 (C16, C18). S 2 : Yield: 80%. Ocher solid. M.p.: 135°C. Anal. Calc. for (C 15 H 13 N 3 O 2 S): C, 60.18; H, 4.38; N, 14.04; S, 10.71. Found: C, 60.22; H, 4.40; N, 14.10; S, 10.71%. UV-Vis λmax, nm, (ε, M − 1 cm − 1 ): 205 (3098), 215 (3326), 230 (3353), 235 (3383), 320 (1113), 375 (1891), 378 (1362). FT-IR ν, cm − 1 : 3051 (Ar. –CH), 2968, 2929, 2869 (Alip. –CH), 2220 (CN), 1600 (CH = N), 1590 (Ar. C = C), 1556 − 1474 (NO 2 ) asym , 1357, 1338 (NO 2 ) sym , 734 (C–S–C). 1 H-NMR (400 MHz, CDCl 3 ) δ, ppm: 8.64 (s, H, CH = N), 8.39–7.26 (m, 4H, Ar. –CH), 2.67 (q, 2H, CH 2 ), 2.41 (s, 3H, –CH 3 ), 1.23 (t, 3H, –CH 2 CH 3 ). 13 C-NMR (100 MHz, CDCl 3 ) δ, ppm: 157.40 (C7), 155.80 (C8), 148.63-109.64 (C1-C6, C9-C11, C13), 20.81 (C16), 14.37–13.64 (C15, C17). Synthesis of Pd II complexes (1, 2) PdCl 2 (CH 3 CN) 2 and the appropriate ligand (E)-4-ethyl-2-(2-hydroxybenzylideneamino)-5-methylthiophene-3-carbonitrile ( S 1 ) and (E)-4-ethyl-5-methyl-2-(4-nitrobenzylideneamino)thiophene-3-carbonitrile ( S 2 ) were dissolved in 30 mL of methanol and stirred for 12 hours at room conditions. The resulting precipitates were collected by filtration, washed with many times diethyl ether, and dried in a vacuum over anhydrous CaCl 2 . The product was purified by recrystallization from a dichloromethane/DMF mixture (3:1). The structure of the complexes was proposed as in Fig. 2 . Complex 1 : PdCl 2 (CH 3 CN) 2 (0.34 g, 1.30 mmol) and S 1 (0.70 g, 2.60 mmol) reacted to give the product a black solid (78%). M.p.: 305°C. Anal. Calc. for (C 30 H 29 N 4 O 3 . 5 S 2 Pd): C, 53.61; H, 4.35; N, 8.33; S, 9.54. Found: C, 53.61; H, 5.17; N, 8.36; S, 9.55%. UV-Vis λmax, nm, (ε, M − 1 cm − 1 ): 223 (4000), 233 (3868), 242 (3684), 256 (4020), 273 (3861), 296 (3094), 307 (3965), 315 (3978), 325 (3466), 370 (1049), 380 (1052), 400 (1218), 425 (960), 480 (510). FT-IR ν, cm − 1 : 3430 (OH/H 2 O), 3055, 3013 (Ar. –CH), 2963, 2925, 2869 (Alip. –CH), 2222 (CN), 1605 (CH = N), 1590, 1560, 1526 (Ar. C = C), 1144 (C–O), 849 (H 2 O), 753 (C–S–C) br , 576, 558, 520 (M–O), 470, 457 (M–N). 1 H-NMR (400 MHz, CDCl 3 ) δ, ppm: 8.83 (s, H, CH = N), 7.90–6.99 (m, 4H, Ar. –CH), 4.30 (H 2 O), 2.65 (q, 2H, –CH 2 ), 2.44 (s, 3H, –CH 3 ), 1.32 (t, 3H, -CH 2 C H 3 ). 13 C-NMR (100 MHz, CDCl 3 ) δ, ppm: 162.13 (C7), 149.40 (C2), 145.56 (C8), 134.32–96.05 (C1-C6, C9-C11, C13), 20.15 (C17), 15.04–14.14 (C16, C18). MS [ESI+]: m/z 671.14 (Calc.), 671.759 (Found) [M-H] + . µeff (B.M.): Dia. Molar conductivity (10 − 3 M, DMF): 12.00 Ω −1 cm 2 mol − 1 . Complex 2 : PdCl 2 (CH 3 CN) 2 (0.60 g, 2.33 mmol) and S 2 (0.70 g, 2.33 mmol) reacted to give the product a dark chestnut solid (87%). M.p.: >300 o C. Anal. Calc. for (C 15 H 17 N 3 O 4 SPdCl 2 ): C, 35.11; H, 3.32; N, 8.19; S, 6.24. Found: C, 35.20; H, 3.40; N, 8.21; S, 6.30%. UV–Vis λmax, nm, (ε, M − 1 cm − 1 ): 218 (3439), 220 (4084), 225 (2923), 280 (3848), 320 (905), 345 (1029), 365 (837), 375 (666), 410 (1424). FT-IR ν, cm − 1 : 3529, 3404 (OH/H 2 O) br , 3187, 3051 (Ar. –CH), 2967, 2933, 2869 (Alip. –CH), 2220 (CN), 1634 (CH = N), 1592 (Ar. C = C), 1560 − 1475 (NO 2 ) asym , 1359, 1340 (NO 2 ) sym , 736 (C–S–C) 830 (H 2 O), 561, 546, 518, 506 (M–O), 482, 470, 457 (M–N). 1 H-NMR (400 MHz, CDCl 3 ) δ, ppm: 8.70 (s, H, CH = N), 8.15–7.72 (m, 4H, Ar. –CH), 2.64 (q, 2H, CH 2 ), 2.48 (s, 3H, –CH 3 ), 1.33, 134 (t, 3H, –CH 2 C H 3 ). 13 C-NMR (100 MHz, CDCl 3 ) δ, ppm: 159.15 (C7), 157.10 (C8), 148.62–113.80 (C1-C6, C9-C11, C13), 20.76 (C16), 14.75–12.23 (C15, C17). MS [ESI+]: m/z 514.69 (Calc.), 514.93 (Found) [M + 2H] + . µeff (B.M.): Dia. Molar conductivity (10 − 3 M, DMF): 9.20 Ω −1 cm 2 mol − 1 . Results and discussion Elemental analysis results showed 1:2 and 1:1 (ML 2 and ML) stoichiometry for complexes 1 and 2. The results of the elemental analysis are in agreement with the theoretical calculation results, as was the case with the experimental part. The measured conductivity data showed that the Pd II complexes are not electrolytes and the absence of an ion in the outer sphere coordination of the complexes. The magnetic measurements exhibited diamagnetic behavior as expected. This clearly indicates the characteristics of the square planer d 8 complexes. Fourier transform infrared spectra (FT-IR) of the ligand S 1 showed three important peaks at 3449 cm − 1 , 1619 cm − 1 , and 1166 cm − 1 related to -OH, -HC = N-, and phenolic C-O stretching, respectively. After complexation -HC = N- shows at 1605 cm − 1 and the red shifting is confirmed with nitrogen atom (azomethine) coordination. The coordination by phenolic oxygen is approved by the presence of C-O at a lower frequency in the region 1144 cm − 1 in complex 1. This coordination is also confirmed by the vanish of the ν(OH) band in the complex 1. The appearance of the new low-frequency band of the M-O and M-N vibrations (576 − 520 cm − 1 ) and (470, 457 cm − 1 ) respectively provided further evidence for the coordination of the ligand S 1 and the palladium ion. Moreover, the C-S-C was not altered by complex formation. These results showed the bidentate nature of the ligand S 1 coordination with the metal ion via the N of the -HC = N- and the O of the hydroxyl group after deprotonation. The lattice waters were observed at 3430 cm − 1 . The FT-IR spectra of the ligand S 2 showed the moderate band at 1600 cm − 1 belonging to stretching vibration of -HC = N-, while this band was shifted to a higher frequency at 1634 cm − 1 for complex 2. This shift confirms the coordination of Pd through the azomethine nitrogen (Patil and Vibhute 2021 ). The asymmetrical and symmetrical stretching vibrations of NO 2 were showed in the range of 1560, 1475, and 1359, 1340 cm − 1 . Upon complexation, no significant change was observed in the NO 2 stretching frequency of the ligand. The broad band at 3529, 3404 cm − 1 was ascribed to stretching vibrations of water molecule coordinated to the complex 2. A band at 830 cm − 1 in complex 2 was due to the coordinated water molecule. The synthesized complex 2 showing spectral bands in 482 − 457 cm − 1 and 561 − 506 cm − 1 range may be mainly due to the formation of M-N and M-O bonds. These bands are absent in the spectra of the ligand S 2 as a result of coordinate N and O atoms with metal ions. The NMR data of ligands S 1 and S 2 and their Pd II complexes were given in the experimental section. The –OH chemical shifts observed in the ligand S 1 in at 11.99 ppm disappeared in the spectra of the complex 1. This clearly indicates the strong involvement of the OH group in chelating by deprotonating the phenol hydrogen. In complex 1, the azomethine peak appeared at 8.83 ppm compared to 8.50 ppm in the ligand S 1 . In complex 2, the azomethine peak appeared at 8.70 ppm compared to 8.64 ppm in the ligand S 2 . These lower frequencies are a result of coordination to the azomethine nitrogen. The proton aromatic groups were observed in 8.39–6.95 ppm. In the 13 C NMR spectra, the -HC = N- carbons in the ligands S 1 and S 2 are observed as singlets in at 161.23 ppm and 157.40 ppm. They were shifted downfield to the region of 162.13 ppm and 159.15 ppm in the spectra of complexes 1 and 2. This shifting promotes the coordination of the azomethine N to the Pd ion. The formation of the complexes was demonstrated using mass spectrometry. The [M-H] + and [M + 2H] + peaks can be shown in the mass spectra in Figs. S17-S18 (see supplementary materials). UV-vis analysis of both ligands and Pd II complexes was carried out in the range of 200–800 nm in DMF at 25°C. An absorption bands in the range of 204–395 nm were observed for ligands S 1 and S 2 . These observed peaks in the ligands are ascribed to intraligand, spin allowed π → π* and n → π*transitions in the UV spectra. After complexation, the peaks observed in the range of 204–290 nm in the ligands were lightly blue-shifted to 223–296 nm and 218–280 nm in Pd II complex spectra. Moreover, new absorption bands that formed between 307–480 nm belong to metal-ligand charge transfer transitions. Thermal analyses of complexes 1, 2 Thermogravimetric analyses (TGA-DTA) were used to study the thermal behavior of complexes 1 and 2. TGA data of complexes 1 and 2 was given in Table 1 . The steps of decomposition, the decomposition products, the temperature ranges and the percentages of weight loss of complexes 1 and 2 were calculated on the basis of the thermograms. They showed agreement between their thermal decomposition results and the calculated values, which validates the elemental analysis and the proposed equations. The temperature progressed from 50 to 900°C and its heating rate was 10°C min − 1 . Both complexes showed a loss of mass in one step. The first step occurred in the temperature range 50–530°C and 50–800°C with a corresponding weight loss of 49.50% (calc. 50.62%) and 38.93% (calc. 40.74%) for complexes 1 and 2, respectively. It was found that the remaining palladium metal + organic moiety in complexes 1 and 2 (Olesya and Alexander 2020 ). Table 1 Thermal analysis of complexes 1 and 2 Compounds Stage Decomp. Temp. (°C) Weight loss (%) Calc./Found Decomposition product Complex 1 1 50–530 50.62 49.50 C 18 H 24 O 2.5 N 2 S Residue 540- 49.33 50.27 C 12 H 5 N 2 OSPd Complex 2 1 50–800 40.74 38.93 2H 2 O, Cl 2 C 3 H 6 O 2 N 2 Residue 800- 59.21 57.39 C 12 H 7 NSPd Palladium Catalysts Suzuki-Miyaura coupling reaction On the basis of previous studies by our group, the choice of solvent was ethanol:water mixture and the choice of base was K 2 CO 3 (Turan et al. 2022 ). Due to the nature of green chemicals, it has been reported that water is highly preferred and dissolves very well in a water/ethanol mixture (3:1) depending on the structure of complex compounds. Moreover, the best result of base selection is obtained with K 2 CO 3 . Thus it is seen that the best base is K 2 CO 3 , which is a good base for coupling reactions of Pd II Schiff base complex under atmospheric conditions as a catalyst. The structure of the Pd II complexes (1 and 2) used as a catalyst in this study is similar to the previously published Pd(II) Schiff base complexes (Turan et al. 2022 ). Therefore, the optimal conditions for the Suzuki and Heck cross-coupling reactions that we previously determined were used in this study. In this study, in the Pd II complexes (1 and 2), we experimented with electro-attractive groups by removing the nitrogen-containing pyridine ring on the Schiff base ligand. We thought that the efficiency of the Pd II complexes in the catalytic cycle might be affected by these substituents and the absence of the pyridine ring. To optimize the reaction conditions, p -bromobenzonitrile was stirred with phenylboronic acid in the presence of complex 1 as a model reaction (Fig. 3 ). The results of the study are summarized in Tables 2 , 3 . In order to find the ideal coupling reaction parameters, different solvents, catalyst amounts and temperature conditions were investigated. Initially, a low yield (28%) of the corresponding product was performed by GC (Table 2 and Table 3 , entry 1) after stirring the reaction mixture at 25°C (r.t) for 2 h in a 25 mL Schlenk tube p -bromobenzonitrile (2.0 mmol), phenylboronic acid (3.0 mmol) and Pd II complexes (1 and 2) (0.01 mmol) in ethanol:water (1:3) (4 mL). With an increase in the amount of catalyst (0.01 to 0.02 mmol %), no significant improvement in the result was obtained after a longer reaction time (Table 2 , entry 14). When Table 3 is analyzed, it is seen that the best conversion was achieved with 91% yield at 80°C in the presence of K 2 CO 3 . When the lowest temperature and the shortest reaction time were tried within the framework of green chemistry principles, it was observed that the yields were quite low. It was also observed that increasing the amount of catalyst had no effect on changing the optimum conditions created. Table 2 Screening of amount of Pd II complex, base, temperature and time for the Suzuki-Miyaura reaction Entry Pd II cat. Base Temp. (°C) Time (h) Yield (%) 1 1 NaOH 25 3 28 2 1 Cs 2 CO 3 25 3 24 3 1 KOH 25 3 38 4 1 K 2 CO 3 25 3 61 5 1 KOBu t 25 3 29 6 1 NaOH 80 3 48 7 1 Cs 2 CO 3 80 3 54 8 1 KOH 80 3 64 9 1 K 2 CO 3 80 3 100 10 1 KOBu t 80 3 49 11 1 - 80 3 - 12 1 K 2 CO 3 80 2 100 13 1 K 2 CO 3 80 1.5 73 14 1 K 2 CO 3 80 2 100* 15 1 K 2 CO 3 80 2 35** Reaction conditions Phenyl boronic acid (3.0 mmol), catalyst (0.01 mmol), base (4.0 mmol), aryl halide (2.0 mmol), EtOH/H 2 O (4 mL), and 80°C. * Amount of catalyst (Pd II comp. (0.02 mmol)), ** When no catalyst was used. When Table 4 was evaluated, organic and inorganic solvents were tried and the best solvent system was investigated. The best choice of solvent was found to be ethanol-water mixture. Table 3 Solvent effect in Suzuki-Miyaura reaction Entry Solvent Time (h) Yield (%) 1 Et-OH 3 70 2 Met-OH 3 65 3 CH 3 CN 3 42 4 Toluene 3 54 5 DMF 3 44 6 THF 3 40 7 Dioxane 3 52 8 i- PrOH + H 2 O 3 74 9 Et-OH + H 2 O 2 91 10 H 2 O 2 74 Reaction conditions Phenyl boronic acid (3.0 mmol), aryl halide (2.0 mmol), base (4.0 mmol), catalyst (0.01 mmol), EtOH/H 2 O (4 mL), and 80°C. Table 4 shows that when p -bromoacetonitrile, p -bromobenzaldehyde, p -bromoanisole, p -bromotoluene and bromobenzene were used as aryl halides, the desired products exhibited very good catalytic activity with excellent conversions ranging from 91%-100% in the coupling reactions with phenylboronic acid. When compared with the literature studies on the catalytic activity of Schiff base complexes, it can be said that this high activity is due to the electronic and structural properties of the ligand. In addition, in both Pd II complexes (1 and 2) used as catalysts, it is seen that the electron withdrawing groups on the aromatic ring do not affect the catalytic activities. Therefore, it can be seen from experiments 1 and 8 in Table 4 that the electron withdrawing and electron donating group in the p -position almost do not affect the activity. When Table 4 experiments 9 and 10 are evaluated, it is seen that both complexes provide catalytic conversion with 100% efficiency when bromobenzene is used as substrate. Table 4 Suzuki-Miyaura coupling reactions catalyzed by Pd II complexes Entry Pd II comp. Aryl halide Time (h) Temp. (ºC) Yield (%) 1 1 p -bromobenzonitrile 2 80 100 2 2 97 3 1 p -bromobenzaldehyde 2 80 100 4 2 96 5 1 p -bromoanisole 2 80 97 6 2 87 7 1 p -bromotoluene 2 80 91 8 2 90 9 1 bromobenzene 2 80 100 10 2 100 Finally, Pd II complexes ( 1 and 2 ) bearing electron withdrawing groups were used as catalysts in the C-C coupling reaction of aryl bromides ( p -bromoacenitrile, p- bromoanisole and p -bromotoluene, p -bromobenzaldehyde, bromobenzene) with phenylboronic acid. The Pd II complexes (1 and 2) showed excellent activity of 87–100% in these reactions. The use of p -bromoacetnitrile (electron-withdrawing group) or p -bromotoluene (electron-donating group) as substrates did not significantly differ in terms of catalytic activity, whether the aryl bromides used were electro-attractive or electro-absorbing. Both complexes were seen to be active catalysts in the Suzuki-Miyaura reactions (Table 4 , entries 1 to 10). Mizoroki-Heck coupling reaction Palladium complex (0.01 mmol), aryl halide (2 mmol), styrene (3 mmol), and K 2 CO 3 (4 mmol) in ethanol/water (4 mL) were added to a two-necked round-bottomed flask containing magnetic fish for 2 h. The mixture was heated at 80°C using an oil bath and the progress was checked using thin layer chromatography (TLC). The mixture was extracted with ethyl acetate and passed through MgSO 4 to be submitted to GC-MS. Table 5 Mizoroki Heck coupling of styrene and aryl bromides in Pd II complexes (1 and 2) Entry Pd(II) comp. Aryl halide Time (h) Temp. (ºC) Yield (%) 1 1 p -bromobenzonitrile 2 80 75 2 2 74 3 1 p -bromobenzaldehyde 2 80 78 4 2 77 5 1 p -bromoanisole 2 80 76 6 2 75 7 1 p -bromotoluene 2 80 73 8 2 72 9 1 bromobenzene 2 80 75 10 2 76 Reaction conditions Styrene (3.0 mmol), aryl halide (2.0 mmol), base (4.0 mmol), catalyst (0.01 mmol), EtOH/H 2 O (4 mL), 2 s, 80°C. In the Mizoroki-Heck coupling reaction, good catalytic transformations ranging from 72–78% were obtained in the reaction of p -bromoacetonitrile with styrene as substrate (Fig. 4 ). Table 5 shows that all bromoaryl halides used as substrates exhibited yields close to each other. It was also observed that the electronic and structural properties of the Pd II complexes used as both catalysts did not significantly affect the yields. It was observed that styrene used as olefin did not provide very high yields due to its structural properties. As a result, palladium complexes of both ligands were found to be moderate activity in Mizoroki-Heck coupling reactions. Both Pd II complexes obtained were found to be very important catalyst systems in the Mizoroki-Heck coupling reaction in terms of environmentally friendly and short reaction time compared to the literature. It is thought that the present study will lead to the creation of many novel catalyst systems. Conclusion In the current work, both the ligands, S 1 and S 2 , and their complexes 1 , 2 have been synthesized and characterized with several analytical and spectral techniques. The conversion of the products obtained at the end of the catalytic trials was ascertained used by a GC-MS device. Based on the results of the analyses and literature studies, a square planar structure for the complexes was proposed. The catalytic activities of the synthesized complexes 1 and 2 were also tested in the Suzuki-Miyaura and Mizoroki-Heck C-C reactions. From the results of catalytic activity, the complexes 1 and 2 found to be very capable of carrying out the Suzuki-Miyaura coupling reaction. At the required reaction times, the complexes 1 and 2 were shown to undergo Suzuki cross-coupling reaction between the sterically hindered and deactivated aryl bromides and phenylbronic acid. In addition, complexes 1 and 2 showed good conversion and selectivity in short times at low catalyst loads. In the Mizoroki-Heck coupling reaction, it was observed that they provided good conversion at 72–78%. Declarations Conflict of Interest No conflict of interest declared Acknowledgment This study was supported by Scientific Research Coordination Unit of Muş Alparslan University. Project number: BAP-22-FEF-4902-05. The authors would like thank BAP’s the financial support. References Alonso F, Beletskaya IP, Yus M (2005) Non-conventional methodologies for transition-metal catalyzed carbon-carbon coupling: a critical overview. Part 1: The Heck reaction. Tetrahedron 61:11771–11835. https://doi.org/10.1016/j.tet.2005.08.054 Amatore C, El Kaïm L, Grimaud L, Jutand A, Meignié A, Romanov G (2014) Kinetic data on the synergetic role of amines and water in the reduction of phosphine-ligated palladium(II) to palladium(0). Eur J Org Chem 2014:4709–4713. https://doi.org/10.1002/ejoc.201402519 Andrews MJ, Brunen S, McIntosh RD, Mansell SM (2023) Preformed Pd(II) catalysts based on monoanionic [N,O] ligands for Suzuki-Miyaura cross-coupling at low temperature. Catalysts 13:303. https://doi.org/10.3390/catal13020303 Baysal A, Aydemir M, Durap F, Gümgüm B, Özkar S, Yıldırım LT (2007) Synthesis and characterizations of 3,3'-bis(diphenylphosphinoamine)-2,2'-bipyridine and 3,3'-bis(diphenylphosphinite)-2,2'-bipyridine and their chalcogenides. Polyhedron 26:3373–3378. https://doi.org/10.1016/j.poly.2007.03.027 Beller M, Zapf A, Riermeier TH (2004) Palladium-catalyzed olefinations of aryl halides (Heck reaction) and related transformations. In: Beller M, Bolm C (eds) Transition metals for organic synthesis, second edn. Wiley-VCH, Weinheim, Germany, pp 271–305 Billingsley K, Buchwald SL (2007) Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters. J Am Chem Soc 129:3358–3366. https://doi.org/10.1021/ja068577p Biricik N, Kayan C, Gumgum B, Fei Z, Scopelliti R, Dyson PJ, Gurbuz N, Ozdemir I (2015) Synthesis and characterization of ether-derivatized aminophosphines and their application in C-C coupling reactions. Inorg Chim Acta 363:1039–1047. https://doi.org/10.1016/j.ica.2009.12.020 Bondar DV, Vhanale BT, Ingle VS (2023) Synthesis, spectral characterization and antimicrobial, antioxidant properties of Au(III), Pd(II), Cu(II), Fe(II) and Mn(II) metal complexes of 1-hydroxy-2-acetonaphthone Schiff base. 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Catalysts 11:755. https://doi.org/10.3390/catal11070755 Montoya V, Pons J, Branchadell V, Garcia-Antón J, Solans X, Font-Bardia M, Ros J (2008) Highly efficient pyridylpyrazole ligands for the Heck reaction. A combined experimental and computational study. Organometallics 27:1084–1091. https://doi.org/10.1021/om7009182 Nagalakshmi V, Sathya M, Premkumar M, Kaleeswaran D, Venkatachalam G, Balasubramani K (2020) Palladium(II) complexes comprising naphthylamine and biphenylamine based Schiff base ligands: Synthesis, structure and catalytic activity in Suzuki coupling reactions. J Organomet Chem 914:121220. https://doi.org/10.1016/j.jorganchem.2020.121220 Nasaruddin NH, Ahmad SN, Sirat SS, Tan KW, Zakaria NA, Mohamad Nazam SS, Tan KW, Zakaria NA, Nazam SSM, Abd Rahman NMM, Mohd Yusof NS, Bahron H (2022) Synthesis, structural characterization, hirshfeld surface analysis, and antibacterial study of Pd(II) and Ni(II) Schiff base complexes derived from aliphatic diamine. ACS Omega 7(47):42809–42818. https://doi.org/10.1016/j.molstruc.2023.136386 Niakan M, Asadi Z, Masteri-Farahani M (2018) A covalently anchored Pd(II)-Schiff base complex over a modified surface of mesoporous silica SBA-16: An efficient and reusable catalyst for the Heck-Mizoroki coupling reaction in water. Colloids Surf A: Physicochem Eng Asp 551:117–127. https://doi.org/10.1016/j.colsurfa.2018.04.066 Olesya S, Alexander P (2020) Antimicrobial activity of mono-and polynuclear platinum and palladium complexes. Foods Raw Mater 8(2):298–311. https://doi.org/10.21603/2308-4057-2020-2-298-311 Patil SK, Vibhute BT (2021) Synthesis, characterization, anticancer and DNA photocleavage study of novel quinoline Schiff base and its metal complexes. Arab J Chem 14(8):103285. https://doi.org/10.1016/j.arabjc.2021.103285 Paul S, Barman P (2024) Exploring diaminomaleonitrile-derived Schiff base ligand and its complexes: Synthesis, characterization, computational insights, biological assessment, and molecular docking. J Mol Struct 1296:136941. https://doi.org/10.1016/j.molstruc.2023.136941 Schmid M, Eberhardt R, Klinga M, Leskela M, Rieger B (2001) New C2v- and Chiral C2-symmetric olefin polymerization catalysts based on nickel(II) and palladium(II) diimine complexes bearing 2,6-diphenyl aniline moieties: Synthesis, structural characterization, and first insight into polymerization properties. Organometallics 20:2321–2330. https://doi.org/10.1021/om010001f Scott NWJ, Ford MJ, Jeddi N, Eyles A, Simon L, Whitwood AC, Tanner T, Willans C, Fairlamb EIJS (2015) A dichotomy in cross-coupling site selectivity in a dihalogenated heteroarene: Influence of mononuclear Pd, Pd clusters, and Pd nanoparticles-the case for exploiting Pd catalyst speciation. J Am Chem Soc 143:9682–9693. https://doi.org/10.1002/ejoc.201402519 Talat B, Nuray YB, Ayfer M (2018) A new air and moisture stable robust bio-polymer based palladium catalyst for highly efficient synthesis of biaryl compounds. Appl Organometal Chem 32:e4076. https://doi.org/10.1002/aoc.4076 Turan N, Buldurun K, Bursal E, Mahmoudi G (2022) Pd(II)-Schiff base complexes: Synthesis, characterization, Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions, enzyme inhibition and antioxidant activities. J Organomet Chem 970–971:122370. https://doi.org/10.1016/j.jorganchem.2022.122370 Yaşar S, Şahin Ç, Arslan M, Özdemir İ (2015) Synthesis, characterization and the Suzuki-Miyaura coupling reactions of N-heterocyclic carbine-Pd(II)-pyridine (PEPPSI) complexes. J Organomet Chem 776:107–112. https://doi.org/10.1016/j.jorganchem.2014.10.047 Yousif E, Majeed A, Al-Sammarrae K, Salih N, Salimon J, Abdullah B (2017) Metal complexes of Schiff base: Preparation, characterization and antibacterial activity. Arab J Chem 10:S1639–S1644. https://doi.org/10.1016/j.arabjc.2013.06.006 Supplementary Files GraphicalAbstract.tif SuplementaryMaterial.docx Cite Share Download PDF Status: Posted Version 1 posted You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. 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Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-3913928","acceptedTermsAndConditions":true,"allowDirectSubmit":true,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":274766257,"identity":"1f8523e3-9037-4c42-87a9-046b59084d67","order_by":0,"name":"Nevin 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13:11:36","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-3913928/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-3913928/v1","draftVersion":[],"editorialEvents":[],"editorialNote":"","failedWorkflow":false,"files":[{"id":51766753,"identity":"9a2804f4-6955-4602-8ae5-f1bd4920b20b","added_by":"auto","created_at":"2024-02-28 18:56:17","extension":"png","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":26190,"visible":true,"origin":"","legend":"\u003cp\u003eSchiff base ligand (S\u003csup\u003e1\u003c/sup\u003e and S\u003csup\u003e2\u003c/sup\u003e)\u003c/p\u003e","description":"","filename":"Onlinefloatimage1.png","url":"https://assets-eu.researchsquare.com/files/rs-3913928/v1/68a3ce6c24488756b71756d1.png"},{"id":51766755,"identity":"9c95d0ec-3784-44cc-9c0b-3c8dd8d544a1","added_by":"auto","created_at":"2024-02-28 18:56:18","extension":"png","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":8318,"visible":true,"origin":"","legend":"\u003cp\u003ePd\u003csup\u003eII\u003c/sup\u003e complexes (1 and 2)\u003c/p\u003e","description":"","filename":"Onlinefloatimage2.png","url":"https://assets-eu.researchsquare.com/files/rs-3913928/v1/294fda26bc7e2b7b2540493e.png"},{"id":51766748,"identity":"865b9dce-8df6-4a64-85ab-98ddcd71ecf9","added_by":"auto","created_at":"2024-02-28 18:56:17","extension":"png","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":2671,"visible":true,"origin":"","legend":"\u003cp\u003eSuzuki-Miyaura reactions of aryl halide and phenylboronic acid\u003c/p\u003e","description":"","filename":"Onlinefloatimage3.png","url":"https://assets-eu.researchsquare.com/files/rs-3913928/v1/e34501b218bc2d8e85a4c2d5.png"},{"id":51766749,"identity":"4cf3e3b4-a50e-455b-b042-9cf15103a9e8","added_by":"auto","created_at":"2024-02-28 18:56:17","extension":"png","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":2203,"visible":true,"origin":"","legend":"\u003cp\u003eMizoroki Heck coupling reactions of aryl halide and styrene\u003c/p\u003e","description":"","filename":"Onlinefloatimage4.png","url":"https://assets-eu.researchsquare.com/files/rs-3913928/v1/1a0aabe4e37800ea6206ea5f.png"},{"id":53064189,"identity":"dd2407be-7e18-4039-bba3-006c8a7cfb23","added_by":"auto","created_at":"2024-03-20 07:56:23","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":521650,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-3913928/v1/17b2b510-fe72-4b56-ab7d-7aaa4d7d273c.pdf"},{"id":51766750,"identity":"4ae8c16c-d6b9-4f22-a0a5-d984d4283918","added_by":"auto","created_at":"2024-02-28 18:56:17","extension":"tif","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":463494,"visible":true,"origin":"","legend":"","description":"","filename":"GraphicalAbstract.tif","url":"https://assets-eu.researchsquare.com/files/rs-3913928/v1/8ba9fb1f069283938cd41c92.tif"},{"id":51766744,"identity":"c946145b-16c8-4aff-a1fc-3565e816fea1","added_by":"auto","created_at":"2024-02-28 18:56:16","extension":"docx","order_by":2,"title":"","display":"","copyAsset":false,"role":"supplement","size":2363175,"visible":true,"origin":"","legend":"","description":"","filename":"SuplementaryMaterial.docx","url":"https://assets-eu.researchsquare.com/files/rs-3913928/v1/dd8122e58d137e99fe4c0ed4.docx"}],"financialInterests":"","formattedTitle":"Synthesis, Characterization of Two New Schiff Base and Their PdII Complexes and Investigation of Palladium Catalyzed Cross-Coupling Reactions","fulltext":[{"header":"Introduction","content":"\u003cp\u003ePalladium catalyzed cross-coupling reactions are considered to be powerful tools and important fields range in organic synthesis, natural products, and materials sciences (Heck \u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e1985\u003c/span\u003e; Maluenda and Navarro \u003cspan citationid=\"CR16\" class=\"CitationRef\"\u003e2015\u003c/span\u003e; Biricik et al. 2010). Palladium-catalyzed Suzuki-Miyaura C-C reactions between aryl halides and aryl boronic acids are a powerful tool in modern synthetic chemistry (Corbet and Mignani \u003cspan citationid=\"CR10\" class=\"CitationRef\"\u003e2006\u003c/span\u003e). The reaction is usually catalyzed by palladium catalyst precursors, ligands binding to the palladium center and stabilizing the catalyst during the reaction process, and bases capturing the boronate group. Choosing the right ligands is crucial in determining how the reaction proceeds (Zhang et al. 2021). The Suzuki-Miyaura C-C reaction has the exceptional advantages of proven efficiency, compatibility with a wide range of functional groups, and mild reaction conditions. It is widely used in industrial synthesis and is the primary method for C-C bond formation for organic synthetic chemistry. The importance of palladium-catalyzed C-C bond formation reactions has led the chemical community to search for highly active and stable palladium-based catalysts, which should also be versatile and efficient systems (Beller et al. \u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e2004\u003c/span\u003e; Yaşar et al. \u003cspan citationid=\"CR29\" class=\"CitationRef\"\u003e2015\u003c/span\u003e). A powerful tool in organic synthesis for the formation of C-C bond is the palladium-catalyzed arylation or vinylation of olefins, also known as the Mizoroki-Heck reaction (Alonso et al. \u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e2005\u003c/span\u003e; Montoya et al. \u003cspan citationid=\"CR18\" class=\"CitationRef\"\u003e2008\u003c/span\u003e). A review of the literature shows that this reaction has been carried out using many phosphine-based palladium catalysts (Baysal et al. \u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e2007\u003c/span\u003e; Amatore et al. \u003cspan citationid=\"CR2\" class=\"CitationRef\"\u003e2014\u003c/span\u003e; Scott et al. 2021). The phosphine ligands are toxic, sensitive to air, expensive, and difficult to synthesize. To overcome these traditional disadvantages, the search has been on for the rational design of new catalysts for C-C bond formation reactions. Among the different metal catalysts, various ligand-palladium(0) or palladium(II) homogeneous complexes show an excellent performance as a catalyst in the Mizoroki-Heck coupling reaction (Buldurun et al. \u003cspan citationid=\"CR9\" class=\"CitationRef\"\u003e2019\u003c/span\u003e;. Matsheku et al. \u003cspan citationid=\"CR17\" class=\"CitationRef\"\u003e2021\u003c/span\u003e; Niakan et al. \u003cspan citationid=\"CR21\" class=\"CitationRef\"\u003e2018\u003c/span\u003e). The influence of the Mizoroki-Heck coupling reaction in organic synthesis over the last few decades is also clearly demonstrated by the presence of publications on Mizoroki-Heck coupling reactions in the literature (Nagalakshmi et al. \u003cspan citationid=\"CR19\" class=\"CitationRef\"\u003e2020\u003c/span\u003e; Gur\u0026rsquo;eva et al. \u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e2019\u003c/span\u003e; Turan et al. \u003cspan citationid=\"CR28\" class=\"CitationRef\"\u003e2022\u003c/span\u003e).\u003c/p\u003e \u003cp\u003eSchiff bases are very common ligands in organometallic chemistry. Schiff bases coordinate to metal ions via the nitrogen atom of the azomethine (Yousif et al. \u003cspan citationid=\"CR30\" class=\"CitationRef\"\u003e2017\u003c/span\u003e). Numerous industrial applications have arisen from the ease of synthesis of Schiff base ligands and the thermal and chemical stability of the resulting complexes. Schiff base-palladium(II) complexes appear to be active and suitable for the preparation of target compounds due to their ease of preparation and commercial availability (Billingsley and Buchwald \u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e2007\u003c/span\u003e; Ingoglia et al. \u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e2019\u003c/span\u003e). They have been widely used as catalysts in various organic reactions, such as olefinic polymerizations, olefinic hydrogenations, and toxic metal removal (Domin et al. \u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e2005\u003c/span\u003e; Schmid et al. \u003cspan citationid=\"CR25\" class=\"CitationRef\"\u003e2001\u003c/span\u003e; Talat et al. \u003cspan citationid=\"CR27\" class=\"CitationRef\"\u003e2018\u003c/span\u003e). Schiff base complexes or frameworks have many applications in biochemistry, chemicals as catalysts, chemo-sensors, dyes and pigments, polymerization and fluorescence, organic lighting devices (Bondar et al. \u003cspan citationid=\"CR8\" class=\"CitationRef\"\u003e2023\u003c/span\u003e; Paul and Barman \u003cspan citationid=\"CR24\" class=\"CitationRef\"\u003e2024\u003c/span\u003e; Andrews et al. \u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e2023\u003c/span\u003e; Nasaruddin et al. \u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e2022\u003c/span\u003e).\u003c/p\u003e \u003cp\u003eThus, in continuation of our research interest in the synthesis, physicochemical and spectroscopic characterization, and catalytic applications of transition metal complexes we report here new Pd\u003csup\u003eII\u003c/sup\u003e complexes as an efficient catalyst in Suzuki-Miyaura and Mizoroki-Heck reactions. In this study, two new Schiff base ligands (\u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e1\u003c/b\u003e\u003c/sup\u003e and \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e2\u003c/b\u003e\u003c/sup\u003e) and their Pd\u003csup\u003eII\u003c/sup\u003e metal complexes were synthesized and their structures were elucidated. Then the catalytic activities of the synthesized Pd\u003csup\u003eII\u003c/sup\u003e complexes (1 and 2) in Suzuki-Miyaura and Mizoroki-Heck coupling reactions were determined. The development of new palladium catalysts with high conversion, reaction rates, yields, and selectivity is in high demand on the market.\u003c/p\u003e"},{"header":"Experimental","content":"\u003cdiv id=\"Sec3\" class=\"Section2\"\u003e \u003ch2\u003eMaterials and instrumentation\u003c/h2\u003e \u003cp\u003e2-hydroxybenzaldehyde, 4-nitrobenzaldehyde, glacial acetic acid, PdCl\u003csub\u003e2\u003c/sub\u003e(CH\u003csub\u003e3\u003c/sub\u003eCN)\u003csub\u003e2\u003c/sub\u003e, phenylboronic acid, styrene, CaCl\u003csub\u003e2\u003c/sub\u003e, KBr, KOH, NaOH, Na\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e, K\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e, KOBu\u003csup\u003et\u003c/sup\u003e, Cs\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e, MgSO\u003csub\u003e4\u003c/sub\u003e, CH\u003csub\u003e3\u003c/sub\u003eCN, ethyl alcohol, ethyl acetate, toluene, \u003cem\u003ei\u003c/em\u003e-propanol, triethylamine, DCM, DMSO, DMF, dioxane, chloroform, acetone, methanol, hexane, water and diethyl ether were used as chemicals/reagents. All reagents and solvent used in study were purchased from Sigma-Aldrich and used without additional drying and purification. All of the synthesis was performed using the standard Schlenk tube technique in an inert gas atmosphere. The elemental analyses were carried out using a Thermos Scientific Flas 2000 CNSO analyzer. FT-IR spectra were recorded in the range 400\u0026ndash;4000 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e on PerkinElmer Spectrum 65. \u003csup\u003e1\u003c/sup\u003eH and \u003csup\u003e13\u003c/sup\u003eC NMR spectra were performed using a Bruker UPB Avance-III 400 MHz NMR spectrometer. UV\u0026ndash;Vis spectra were measurement as DMF solutions using a Shimadzu UV-1800 spectrophotometer. Magnetic susceptibility was performed using the Guoy method with Hg[(Co(SCN)\u003csub\u003e4\u003c/sub\u003e] as calibrant on the Sherwood Auto Magnetic Susceptibility Balance. The C-C coupling products (recorded in the catalytic reactions) were analyzed used with GC-FID Chromatograph methods. Mass Spectrometer Agilent Technologies 6890N. The melting points were determined using an electro-thermal 9200 melting point apparatus. The conductivity of the Pd\u003csup\u003eII\u003c/sup\u003e complexes was measured with the Jenway 4010 conductivity meter in 10\u003csup\u003e\u0026minus;\u0026thinsp;3\u003c/sup\u003e M DMF.\u003c/p\u003e \u003cp\u003e \u003cb\u003eSynthesis and characterization of (\u003c/b\u003e \u003cb\u003eE\u003c/b\u003e \u003cb\u003e)-4-ethyl-2-(2-hydroxybenzylideneamino)-5-methylthiophene-3-carbonitrile (S\u003c/b\u003e \u003csup\u003e \u003cb\u003e1\u003c/b\u003e \u003c/sup\u003e \u003cb\u003e) and (\u003c/b\u003e \u003cb\u003eE\u003c/b\u003e \u003cb\u003e)-4-ethyl-5-methyl-2-(4-nitrobenzylideneamino)thiophene-3-carbonitrile (S\u003c/b\u003e \u003csup\u003e \u003cb\u003e2\u003c/b\u003e \u003c/sup\u003e \u003cb\u003e)\u003c/b\u003e \u003c/p\u003e \u003cp\u003eThe novel ligands \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e1\u003c/b\u003e\u003c/sup\u003e and \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e2\u003c/b\u003e\u003c/sup\u003e were prepared by reacting 2-amino-5-ethyl-4-methylthiophene-3-carbonitrile and 2-hydroxybenzaldehyde (\u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e1\u003c/b\u003e\u003c/sup\u003e) and 4-nitrobenzaldehyde (\u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e2\u003c/b\u003e\u003c/sup\u003e) in the presence of few drops of glacial acetic acid in 20 mL methanol solution for 3 h (characterization data were given in supplementary material). The resulting crude products were recrystallized in hot methanol. The synthesis scheme of the ligands \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e1\u003c/b\u003e\u003c/sup\u003e and \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e2\u003c/b\u003e\u003c/sup\u003e are given in Fig.\u0026nbsp;\u003cspan refid=\"Fig1\" class=\"InternalRef\"\u003e1\u003c/span\u003e.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003cb\u003eS\u003c/b\u003e \u003csup\u003e \u003cb\u003e1\u003c/b\u003e \u003c/sup\u003e: Yield: 85%. Yellow solid. M.p.: 150\u0026deg;C. Anal. Calc. for (C\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eOS): C, 66.64; H, 5.22; N, 10.36; S, 11.86. Found: C, 66.70; H, 5.20; N, 10.35; S, 11.84%. UV-Vis λmax, nm, (ε, M\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e): 204 (3614), 208 (3211), 215 (2576), 230 (2734), 290 (1807), 375 (3153), 385 (3284), 395 (3372). FT-IR ν, cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e: 3449 (\u0026ndash;OH), 3058 (Ar. \u0026ndash;CH), 2967, 2933, 2872 (Alip. \u0026ndash;CH), 2222 (CN), 1619 (CH\u0026thinsp;=\u0026thinsp;N), 1598, 1566, 1492 (Ar. C\u0026thinsp;=\u0026thinsp;C), 1166 (C\u0026ndash;O), 761 (C\u0026ndash;S\u0026ndash;C). \u003csup\u003e1\u003c/sup\u003eH-NMR (400 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e) δ, ppm: 11.99 (s, 1H, \u0026ndash;OH), 8.50 (s, H, CH\u0026thinsp;=\u0026thinsp;N), 7.41\u0026ndash;6.95 (m, 4H, Ar. \u0026ndash;CH), 2.64, 2.63 (q, 2H, CH\u003csub\u003e2\u003c/sub\u003e), 2.39 (s, 3H, \u0026ndash;CH\u003csub\u003e3\u003c/sub\u003e), 1.22 (t, 3H, \u0026ndash;CH\u003csub\u003e2\u003c/sub\u003eC\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eH\u003c/span\u003e\u003csub\u003e3\u003c/sub\u003e). \u003csup\u003e13\u003c/sup\u003eC-NMR (100 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e) δ, ppm: 161.23 (C7), 160.99 (C2), 156.59 (C8), 139.58-107.56 (C1-C6, C9-C11, C13), 20.88 (C17), 14.37\u0026ndash;13.36 (C16, C18).\u003c/p\u003e \u003cp\u003e \u003cb\u003eS\u003c/b\u003e \u003csup\u003e \u003cb\u003e2\u003c/b\u003e \u003c/sup\u003e: Yield: 80%. Ocher solid. M.p.: 135\u0026deg;C. Anal. Calc. for (C\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eS): C, 60.18; H, 4.38; N, 14.04; S, 10.71. Found: C, 60.22; H, 4.40; N, 14.10; S, 10.71%. UV-Vis λmax, nm, (ε, M\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e): 205 (3098), 215 (3326), 230 (3353), 235 (3383), 320 (1113), 375 (1891), 378 (1362). FT-IR ν, cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e: 3051 (Ar. \u0026ndash;CH), 2968, 2929, 2869 (Alip. \u0026ndash;CH), 2220 (CN), 1600 (CH\u0026thinsp;=\u0026thinsp;N), 1590 (Ar. C\u0026thinsp;=\u0026thinsp;C), 1556\u0026thinsp;\u0026minus;\u0026thinsp;1474 (NO\u003csub\u003e2\u003c/sub\u003e)\u003csub\u003easym\u003c/sub\u003e, 1357, 1338 (NO\u003csub\u003e2\u003c/sub\u003e)\u003csub\u003esym\u003c/sub\u003e, 734 (C\u0026ndash;S\u0026ndash;C). \u003csup\u003e1\u003c/sup\u003eH-NMR (400 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e) δ, ppm: 8.64 (s, H, CH\u0026thinsp;=\u0026thinsp;N), 8.39\u0026ndash;7.26 (m, 4H, Ar. \u0026ndash;CH), 2.67 (q, 2H, CH\u003csub\u003e2\u003c/sub\u003e), 2.41 (s, 3H, \u0026ndash;CH\u003csub\u003e3\u003c/sub\u003e), 1.23 (t, 3H, \u0026ndash;CH\u003csub\u003e2\u003c/sub\u003eCH\u003csub\u003e3\u003c/sub\u003e). \u003csup\u003e13\u003c/sup\u003eC-NMR (100 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e) δ, ppm: 157.40 (C7), 155.80 (C8), 148.63-109.64 (C1-C6, C9-C11, C13), 20.81 (C16), 14.37\u0026ndash;13.64 (C15, C17).\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec4\" class=\"Section2\"\u003e \u003ch2\u003eSynthesis of Pd\u003csup\u003eII\u003c/sup\u003e complexes (1, 2)\u003c/h2\u003e \u003cp\u003ePdCl\u003csub\u003e2\u003c/sub\u003e(CH\u003csub\u003e3\u003c/sub\u003eCN)\u003csub\u003e2\u003c/sub\u003e and the appropriate ligand (E)-4-ethyl-2-(2-hydroxybenzylideneamino)-5-methylthiophene-3-carbonitrile (\u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e1\u003c/b\u003e\u003c/sup\u003e) and (E)-4-ethyl-5-methyl-2-(4-nitrobenzylideneamino)thiophene-3-carbonitrile (\u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e2\u003c/b\u003e\u003c/sup\u003e) were dissolved in 30 mL of methanol and stirred for 12 hours at room conditions. The resulting precipitates were collected by filtration, washed with many times diethyl ether, and dried in a vacuum over anhydrous CaCl\u003csub\u003e2\u003c/sub\u003e. The product was purified by recrystallization from a dichloromethane/DMF mixture (3:1). The structure of the complexes was proposed as in Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003e.\u003c/p\u003e \u003cp\u003e \u003cb\u003eComplex 1\u003c/b\u003e: PdCl\u003csub\u003e2\u003c/sub\u003e(CH\u003csub\u003e3\u003c/sub\u003eCN)\u003csub\u003e2\u003c/sub\u003e (0.34 g, 1.30 mmol) and S\u003csup\u003e1\u003c/sup\u003e (0.70 g, 2.60 mmol) reacted to give the product a black solid (78%). M.p.: 305\u0026deg;C. Anal. Calc. for (C\u003csub\u003e30\u003c/sub\u003eH\u003csub\u003e29\u003c/sub\u003eN\u003csub\u003e4\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e.\u003csub\u003e5\u003c/sub\u003eS\u003csub\u003e2\u003c/sub\u003ePd): C, 53.61; H, 4.35; N, 8.33; S, 9.54. Found: C, 53.61; H, 5.17; N, 8.36; S, 9.55%. UV-Vis λmax, nm, (ε, M\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e): 223 (4000), 233 (3868), 242 (3684), 256 (4020), 273 (3861), 296 (3094), 307 (3965), 315 (3978), 325 (3466), 370 (1049), 380 (1052), 400 (1218), 425 (960), 480 (510). FT-IR ν, cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e: 3430 (OH/H\u003csub\u003e2\u003c/sub\u003eO), 3055, 3013 (Ar. \u0026ndash;CH), 2963, 2925, 2869 (Alip. \u0026ndash;CH), 2222 (CN), 1605 (CH\u0026thinsp;=\u0026thinsp;N), 1590, 1560, 1526 (Ar. C\u0026thinsp;=\u0026thinsp;C), 1144 (C\u0026ndash;O), 849 (H\u003csub\u003e2\u003c/sub\u003eO), 753 (C\u0026ndash;S\u0026ndash;C)\u003csub\u003ebr\u003c/sub\u003e, 576, 558, 520 (M\u0026ndash;O), 470, 457 (M\u0026ndash;N). \u003csup\u003e1\u003c/sup\u003eH-NMR (400 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e) δ, ppm: 8.83 (s, H, CH\u0026thinsp;=\u0026thinsp;N), 7.90\u0026ndash;6.99 (m, 4H, Ar. \u0026ndash;CH), 4.30 (H\u003csub\u003e2\u003c/sub\u003eO), 2.65 (q, 2H, \u0026ndash;CH\u003csub\u003e2\u003c/sub\u003e), 2.44 (s, 3H, \u0026ndash;CH\u003csub\u003e3\u003c/sub\u003e), 1.32 (t, 3H, -CH\u003csub\u003e2\u003c/sub\u003eC\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eH\u003c/span\u003e\u003csub\u003e3\u003c/sub\u003e). \u003csup\u003e13\u003c/sup\u003eC-NMR (100 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e) δ, ppm: 162.13 (C7), 149.40 (C2), 145.56 (C8), 134.32\u0026ndash;96.05 (C1-C6, C9-C11, C13), 20.15 (C17), 15.04\u0026ndash;14.14 (C16, C18). MS [ESI+]: \u003cem\u003em/z\u003c/em\u003e 671.14 (Calc.), 671.759 (Found) [M-H]\u003csup\u003e+\u003c/sup\u003e. \u0026micro;eff (B.M.): Dia. Molar conductivity (10\u003csup\u003e\u0026minus;\u0026thinsp;3\u003c/sup\u003e M, DMF): 12.00 Ω\u003csup\u003e\u0026minus;1\u003c/sup\u003e cm\u003csup\u003e2\u003c/sup\u003e mol\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e.\u003c/p\u003e \u003cp\u003e \u003cb\u003eComplex 2\u003c/b\u003e: PdCl\u003csub\u003e2\u003c/sub\u003e(CH\u003csub\u003e3\u003c/sub\u003eCN)\u003csub\u003e2\u003c/sub\u003e (0.60 g, 2.33 mmol) and S\u003csup\u003e2\u003c/sup\u003e (0.70 g, 2.33 mmol) reacted to give the product a dark chestnut solid (87%). M.p.: \u0026gt;300 \u003csup\u003eo\u003c/sup\u003eC. Anal. Calc. for (C\u003csub\u003e15\u003c/sub\u003eH\u003csub\u003e17\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003eSPdCl\u003csub\u003e2\u003c/sub\u003e): C, 35.11; H, 3.32; N, 8.19; S, 6.24. Found: C, 35.20; H, 3.40; N, 8.21; S, 6.30%. UV\u0026ndash;Vis λmax, nm, (ε, M\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e): 218 (3439), 220 (4084), 225 (2923), 280 (3848), 320 (905), 345 (1029), 365 (837), 375 (666), 410 (1424). FT-IR ν, cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e: 3529, 3404 (OH/H\u003csub\u003e2\u003c/sub\u003eO)\u003csub\u003ebr\u003c/sub\u003e, 3187, 3051 (Ar. \u0026ndash;CH), 2967, 2933, 2869 (Alip. \u0026ndash;CH), 2220 (CN), 1634 (CH\u0026thinsp;=\u0026thinsp;N), 1592 (Ar. C\u0026thinsp;=\u0026thinsp;C), 1560\u0026thinsp;\u0026minus;\u0026thinsp;1475 (NO\u003csub\u003e2\u003c/sub\u003e)\u003csub\u003easym\u003c/sub\u003e, 1359, 1340 (NO\u003csub\u003e2\u003c/sub\u003e)\u003csub\u003esym\u003c/sub\u003e, 736 (C\u0026ndash;S\u0026ndash;C) 830 (H\u003csub\u003e2\u003c/sub\u003eO), 561, 546, 518, 506 (M\u0026ndash;O), 482, 470, 457 (M\u0026ndash;N). \u003csup\u003e1\u003c/sup\u003eH-NMR (400 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e) δ, ppm: 8.70 (s, H, CH\u0026thinsp;=\u0026thinsp;N), 8.15\u0026ndash;7.72 (m, 4H, Ar. \u0026ndash;CH), 2.64 (q, 2H, CH\u003csub\u003e2\u003c/sub\u003e), 2.48 (s, 3H, \u0026ndash;CH\u003csub\u003e3\u003c/sub\u003e), 1.33, 134 (t, 3H, \u0026ndash;CH\u003csub\u003e2\u003c/sub\u003eC\u003cspan type=\"Underline\" class=\"Underline\" name=\"Emphasis\"\u003eH\u003c/span\u003e\u003csub\u003e3\u003c/sub\u003e). \u003csup\u003e13\u003c/sup\u003eC-NMR (100 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e) δ, ppm: 159.15 (C7), 157.10 (C8), 148.62\u0026ndash;113.80 (C1-C6, C9-C11, C13), 20.76 (C16), 14.75\u0026ndash;12.23 (C15, C17). MS [ESI+]: \u003cem\u003em/z\u003c/em\u003e 514.69 (Calc.), 514.93 (Found) [M\u0026thinsp;+\u0026thinsp;2H]\u003csup\u003e+\u003c/sup\u003e. \u0026micro;eff (B.M.): Dia. Molar conductivity (10\u003csup\u003e\u0026minus;\u0026thinsp;3\u003c/sup\u003e M, DMF): 9.20 Ω\u003csup\u003e\u0026minus;1\u003c/sup\u003e cm\u003csup\u003e2\u003c/sup\u003e mol\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003c/div\u003e"},{"header":"Results and discussion","content":"\u003cp\u003eElemental analysis results showed 1:2 and 1:1 (ML\u003csub\u003e2\u003c/sub\u003e and ML) stoichiometry for complexes 1 and 2. The results of the elemental analysis are in agreement with the theoretical calculation results, as was the case with the experimental part. The measured conductivity data showed that the Pd\u003csup\u003eII\u003c/sup\u003e complexes are not electrolytes and the absence of an ion in the outer sphere coordination of the complexes. The magnetic measurements exhibited diamagnetic behavior as expected. This clearly indicates the characteristics of the square planer d\u003csup\u003e8\u003c/sup\u003e complexes.\u003c/p\u003e \u003cp\u003eFourier transform infrared spectra (FT-IR) of the ligand \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e1\u003c/b\u003e\u003c/sup\u003e showed three important peaks at 3449 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e, 1619 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e, and 1166 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e related to -OH, -HC\u0026thinsp;=\u0026thinsp;N-, and phenolic C-O stretching, respectively. After complexation -HC\u0026thinsp;=\u0026thinsp;N- shows at 1605 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e and the red shifting is confirmed with nitrogen atom (azomethine) coordination. The coordination by phenolic oxygen is approved by the presence of C-O at a lower frequency in the region 1144 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e in complex 1. This coordination is also confirmed by the vanish of the ν(OH) band in the complex 1. The appearance of the new low-frequency band of the M-O and M-N vibrations (576\u0026thinsp;\u0026minus;\u0026thinsp;520 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e) and (470, 457 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e) respectively provided further evidence for the coordination of the ligand \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e1\u003c/b\u003e\u003c/sup\u003e and the palladium ion. Moreover, the C-S-C was not altered by complex formation. These results showed the bidentate nature of the ligand \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e1\u003c/b\u003e\u003c/sup\u003e coordination with the metal ion via the N of the -HC\u0026thinsp;=\u0026thinsp;N- and the O of the hydroxyl group after deprotonation. The lattice waters were observed at 3430 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e.\u003c/p\u003e \u003cp\u003eThe FT-IR spectra of the ligand \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e2\u003c/b\u003e\u003c/sup\u003e showed the moderate band at 1600 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e belonging to stretching vibration of -HC\u0026thinsp;=\u0026thinsp;N-, while this band was shifted to a higher frequency at 1634 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e for complex 2. This shift confirms the coordination of Pd through the azomethine nitrogen (Patil and Vibhute \u003cspan citationid=\"CR23\" class=\"CitationRef\"\u003e2021\u003c/span\u003e). The asymmetrical and symmetrical stretching vibrations of NO\u003csub\u003e2\u003c/sub\u003e were showed in the range of 1560, 1475, and 1359, 1340 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e. Upon complexation, no significant change was observed in the NO\u003csub\u003e2\u003c/sub\u003e stretching frequency of the ligand. The broad band at 3529, 3404 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e was ascribed to stretching vibrations of water molecule coordinated to the complex 2. A band at 830 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e in complex 2 was due to the coordinated water molecule. The synthesized complex 2 showing spectral bands in 482\u0026thinsp;\u0026minus;\u0026thinsp;457 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e and 561\u0026thinsp;\u0026minus;\u0026thinsp;506 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e range may be mainly due to the formation of M-N and M-O bonds. These bands are absent in the spectra of the ligand S\u003csup\u003e2\u003c/sup\u003e as a result of coordinate N and O atoms with metal ions.\u003c/p\u003e \u003cp\u003eThe NMR data of ligands \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e1\u003c/b\u003e\u003c/sup\u003e and \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e2\u003c/b\u003e\u003c/sup\u003e and their Pd\u003csup\u003eII\u003c/sup\u003e complexes were given in the \u003cspan refid=\"Sec2\" class=\"InternalRef\"\u003eexperimental\u003c/span\u003e section. The \u0026ndash;OH chemical shifts observed in the ligand \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e1\u003c/b\u003e\u003c/sup\u003e in at 11.99 ppm disappeared in the spectra of the complex 1. This clearly indicates the strong involvement of the OH group in chelating by deprotonating the phenol hydrogen. In complex 1, the azomethine peak appeared at 8.83 ppm compared to 8.50 ppm in the ligand S\u003csup\u003e1\u003c/sup\u003e. In complex 2, the azomethine peak appeared at 8.70 ppm compared to 8.64 ppm in the ligand S\u003csup\u003e2\u003c/sup\u003e. These lower frequencies are a result of coordination to the azomethine nitrogen. The proton aromatic groups were observed in 8.39\u0026ndash;6.95 ppm. In the \u003csup\u003e13\u003c/sup\u003eC NMR spectra, the -HC\u0026thinsp;=\u0026thinsp;N- carbons in the ligands \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e1\u003c/b\u003e\u003c/sup\u003e and \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e2\u003c/b\u003e\u003c/sup\u003e are observed as singlets in at 161.23 ppm and 157.40 ppm. They were shifted downfield to the region of 162.13 ppm and 159.15 ppm in the spectra of complexes 1 and 2. This shifting promotes the coordination of the azomethine N to the Pd ion.\u003c/p\u003e \u003cp\u003eThe formation of the complexes was demonstrated using mass spectrometry. The [M-H]\u003csup\u003e+\u003c/sup\u003e and [M\u0026thinsp;+\u0026thinsp;2H]\u003csup\u003e+\u003c/sup\u003epeaks can be shown in the mass spectra in Figs. S17-S18 (see supplementary materials).\u003c/p\u003e \u003cp\u003eUV-vis analysis of both ligands and Pd\u003csup\u003eII\u003c/sup\u003e complexes was carried out in the range of 200\u0026ndash;800 nm in DMF at 25\u0026deg;C. An absorption bands in the range of 204\u0026ndash;395 nm were observed for ligands \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e1\u003c/b\u003e\u003c/sup\u003e and \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e2\u003c/b\u003e\u003c/sup\u003e. These observed peaks in the ligands are ascribed to intraligand, spin allowed π \u0026rarr; π* and n \u0026rarr; π*transitions in the UV spectra. After complexation, the peaks observed in the range of 204\u0026ndash;290 nm in the ligands were lightly blue-shifted to 223\u0026ndash;296 nm and 218\u0026ndash;280 nm in Pd\u003csup\u003eII\u003c/sup\u003e complex spectra. Moreover, new absorption bands that formed between 307\u0026ndash;480 nm belong to metal-ligand charge transfer transitions.\u003c/p\u003e\n\u003ch3\u003eThermal analyses of complexes 1, 2\u003c/h3\u003e\n\u003cp\u003eThermogravimetric analyses (TGA-DTA) were used to study the thermal behavior of complexes 1 and 2. TGA data of complexes 1 and 2 was given in Table\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e. The steps of decomposition, the decomposition products, the temperature ranges and the percentages of weight loss of complexes 1 and 2 were calculated on the basis of the thermograms. They showed agreement between their thermal decomposition results and the calculated values, which validates the elemental analysis and the proposed equations. The temperature progressed from 50 to 900\u0026deg;C and its heating rate was 10\u0026deg;C min\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e. Both complexes showed a loss of mass in one step. The first step occurred in the temperature range 50\u0026ndash;530\u0026deg;C and 50\u0026ndash;800\u0026deg;C with a corresponding weight loss of 49.50% (calc. 50.62%) and 38.93% (calc. 40.74%) for complexes 1 and 2, respectively. It was found that the remaining palladium metal\u0026thinsp;+\u0026thinsp;organic moiety in complexes 1 and 2 (Olesya and Alexander \u003cspan citationid=\"CR22\" class=\"CitationRef\"\u003e2020\u003c/span\u003e).\u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab1\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 1\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eThermal analysis of complexes 1 and 2\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"6\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eCompounds\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eStage\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eDecomp. Temp. (\u0026deg;C)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colspan=\"2\" nameend=\"c5\" namest=\"c4\"\u003e \u003cp\u003eWeight loss (%)\u003c/p\u003e \u003cp\u003eCalc./Found\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c6\"\u003e \u003cp\u003eDecomposition product\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eComplex 1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e50\u0026ndash;530\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e50.62\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e49.50\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003eC\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e24\u003c/sub\u003eO\u003csub\u003e2.5\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eS\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eResidue\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e540-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e49.33\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e50.27\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003eC\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e5\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eOSPd\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eComplex 2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e50\u0026ndash;800\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e40.74\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e38.93\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e2H\u003csub\u003e2\u003c/sub\u003eO, Cl\u003csub\u003e2\u003c/sub\u003e C\u003csub\u003e3\u003c/sub\u003eH\u003csub\u003e6\u003c/sub\u003eO\u003csub\u003e2\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eResidue\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e800-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e59.21\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e57.39\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003eC\u003csub\u003e12\u003c/sub\u003eH\u003csub\u003e7\u003c/sub\u003eNSPd\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cdiv id=\"Sec7\" class=\"Section2\"\u003e \u003ch2\u003ePalladium Catalysts\u003c/h2\u003e \u003cdiv id=\"Sec8\" class=\"Section3\"\u003e \u003ch2\u003eSuzuki-Miyaura coupling reaction\u003c/h2\u003e \u003cp\u003eOn the basis of previous studies by our group, the choice of solvent was ethanol:water mixture and the choice of base was K\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e (Turan et al. \u003cspan citationid=\"CR28\" class=\"CitationRef\"\u003e2022\u003c/span\u003e). Due to the nature of green chemicals, it has been reported that water is highly preferred and dissolves very well in a water/ethanol mixture (3:1) depending on the structure of complex compounds. Moreover, the best result of base selection is obtained with K\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e. Thus it is seen that the best base is K\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e, which is a good base for coupling reactions of Pd\u003csup\u003eII\u003c/sup\u003e Schiff base complex under atmospheric conditions as a catalyst. The structure of the Pd\u003csup\u003eII\u003c/sup\u003e complexes (1 and 2) used as a catalyst in this study is similar to the previously published Pd(II) Schiff base complexes (Turan et al. \u003cspan citationid=\"CR28\" class=\"CitationRef\"\u003e2022\u003c/span\u003e). Therefore, the optimal conditions for the Suzuki and Heck cross-coupling reactions that we previously determined were used in this study. In this study, in the Pd\u003csup\u003eII\u003c/sup\u003e complexes (1 and 2), we experimented with electro-attractive groups by removing the nitrogen-containing pyridine ring on the Schiff base ligand. We thought that the efficiency of the Pd\u003csup\u003eII\u003c/sup\u003e complexes in the catalytic cycle might be affected by these substituents and the absence of the pyridine ring.\u003c/p\u003e \u003cp\u003eTo optimize the reaction conditions, \u003cem\u003ep\u003c/em\u003e-bromobenzonitrile was stirred with phenylboronic acid in the presence of complex 1 as a model reaction (Fig.\u0026nbsp;\u003cspan refid=\"Fig3\" class=\"InternalRef\"\u003e3\u003c/span\u003e). The results of the study are summarized in Tables\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e, \u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e. In order to find the ideal coupling reaction parameters, different solvents, catalyst amounts and temperature conditions were investigated.\u003c/p\u003e \u003cp\u003eInitially, a low yield (28%) of the corresponding product was performed by GC (Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e and Table\u0026nbsp;\u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e, entry 1) after stirring the reaction mixture at 25\u0026deg;C (r.t) for 2 h in a 25 mL Schlenk tube \u003cem\u003ep\u003c/em\u003e-bromobenzonitrile (2.0 mmol), phenylboronic acid (3.0 mmol) and Pd\u003csup\u003eII\u003c/sup\u003e complexes (1 and 2) (0.01 mmol) in ethanol:water (1:3) (4 mL). With an increase in the amount of catalyst (0.01 to 0.02 mmol %), no significant improvement in the result was obtained after a longer reaction time (Table\u0026nbsp;\u003cspan refid=\"Tab2\" class=\"InternalRef\"\u003e2\u003c/span\u003e, entry 14).\u003c/p\u003e \u003cp\u003eWhen Table\u0026nbsp;\u003cspan refid=\"Tab3\" class=\"InternalRef\"\u003e3\u003c/span\u003e is analyzed, it is seen that the best conversion was achieved with 91% yield at 80\u0026deg;C in the presence of K\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e. When the lowest temperature and the shortest reaction time were tried within the framework of green chemistry principles, it was observed that the yields were quite low. It was also observed that increasing the amount of catalyst had no effect on changing the optimum conditions created.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab2\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 2\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eScreening of amount of Pd\u003csup\u003eII\u003c/sup\u003e complex, base, temperature and time for the Suzuki-Miyaura reaction\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"6\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eEntry\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003ePd\u003csup\u003eII\u003c/sup\u003e cat.\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eBase\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eTemp. (\u0026deg;C)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003eTime (h)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c6\"\u003e \u003cp\u003eYield (%)\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eNaOH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e25\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e28\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eCs\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e25\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e24\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eKOH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e25\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e38\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eK\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e25\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e61\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eKOBu\u003csup\u003et\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e25\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e29\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eNaOH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e48\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eCs\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e54\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eKOH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e64\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eK\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e100\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eKOBu\u003csup\u003et\u003c/sup\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e49\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e11\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e-\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e12\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eK\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e100\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e13\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eK\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e1.5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e73\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e14\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eK\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e100*\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e15\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003eK\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c6\"\u003e \u003cp\u003e35**\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003e \u003cstrong\u003eReaction conditions\u003c/strong\u003e \u003cp\u003ePhenyl boronic acid (3.0 mmol), catalyst (0.01 mmol), base (4.0 mmol), aryl halide (2.0 mmol), EtOH/H\u003csub\u003e2\u003c/sub\u003eO (4 mL), and 80\u0026deg;C. \u003cb\u003e*\u003c/b\u003eAmount of catalyst (Pd\u003csup\u003eII\u003c/sup\u003e comp. (0.02 mmol)), \u003cb\u003e**\u003c/b\u003eWhen no catalyst was used.\u003c/p\u003e \u003c/p\u003e \u003cp\u003eWhen Table\u0026nbsp;\u003cspan refid=\"Tab4\" class=\"InternalRef\"\u003e4\u003c/span\u003e was evaluated, organic and inorganic solvents were tried and the best solvent system was investigated. The best choice of solvent was found to be ethanol-water mixture.\u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab3\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 3\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eSolvent effect in Suzuki-Miyaura reaction\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"4\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eEntry\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003eSolvent\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eTime (h)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eYield (%)\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eEt-OH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e70\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eMet-OH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e65\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eCH\u003csub\u003e3\u003c/sub\u003eCN\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e42\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eToluene\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e54\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eDMF\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e44\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eTHF\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e40\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eDioxane\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e52\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003cem\u003ei-\u003c/em\u003ePrOH\u0026thinsp;+\u0026thinsp;H\u003csub\u003e2\u003c/sub\u003eO\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e74\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eEt-OH\u0026thinsp;+\u0026thinsp;H\u003csub\u003e2\u003c/sub\u003eO\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e91\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c2\"\u003e \u003cp\u003eH\u003csub\u003e2\u003c/sub\u003eO\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e74\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003e \u003cstrong\u003eReaction conditions\u003c/strong\u003e \u003cp\u003ePhenyl boronic acid (3.0 mmol), aryl halide (2.0 mmol), base (4.0 mmol), catalyst (0.01 mmol), EtOH/H\u003csub\u003e2\u003c/sub\u003eO (4 mL), and 80\u0026deg;C.\u003c/p\u003e \u003c/p\u003e \u003cp\u003eTable\u0026nbsp;\u003cspan refid=\"Tab4\" class=\"InternalRef\"\u003e4\u003c/span\u003e shows that when \u003cem\u003ep\u003c/em\u003e-bromoacetonitrile, \u003cem\u003ep\u003c/em\u003e-bromobenzaldehyde, \u003cem\u003ep\u003c/em\u003e-bromoanisole, \u003cem\u003ep\u003c/em\u003e-bromotoluene and bromobenzene were used as aryl halides, the desired products exhibited very good catalytic activity with excellent conversions ranging from 91%-100% in the coupling reactions with phenylboronic acid. When compared with the literature studies on the catalytic activity of Schiff base complexes, it can be said that this high activity is due to the electronic and structural properties of the ligand. In addition, in both Pd\u003csup\u003eII\u003c/sup\u003e complexes (1 and 2) used as catalysts, it is seen that the electron withdrawing groups on the aromatic ring do not affect the catalytic activities. Therefore, it can be seen from experiments 1 and 8 in Table\u0026nbsp;\u003cspan refid=\"Tab4\" class=\"InternalRef\"\u003e4\u003c/span\u003e that the electron withdrawing and electron donating group in the \u003cem\u003ep\u003c/em\u003e-position almost do not affect the activity. When Table\u0026nbsp;\u003cspan refid=\"Tab4\" class=\"InternalRef\"\u003e4\u003c/span\u003e experiments 9 and 10 are evaluated, it is seen that both complexes provide catalytic conversion with 100% efficiency when bromobenzene is used as substrate.\u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab4\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 4\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eSuzuki-Miyaura coupling reactions catalyzed by Pd\u003csup\u003eII\u003c/sup\u003e complexes\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"6\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eEntry\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003ePd\u003csup\u003eII\u003c/sup\u003e comp.\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eAryl halide\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eTime (h)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003eTemp. (\u0026ordm;C)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c6\"\u003e \u003cp\u003eYield (%)\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e\u003cem\u003ep\u003c/em\u003e-bromobenzonitrile\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e100\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e2\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e97\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e\u003cem\u003ep\u003c/em\u003e-bromobenzaldehyde\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e100\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e2\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e96\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e\u003cem\u003ep\u003c/em\u003e-bromoanisole\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e97\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e2\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e87\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e\u003cem\u003ep\u003c/em\u003e-bromotoluene\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e91\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e2\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e90\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003ebromobenzene\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e100\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e2\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e100\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003eFinally, Pd\u003csup\u003eII\u003c/sup\u003e complexes (\u003cb\u003e1\u003c/b\u003e and \u003cb\u003e2\u003c/b\u003e) bearing electron withdrawing groups were used as catalysts in the C-C coupling reaction of aryl bromides (\u003cem\u003ep\u003c/em\u003e-bromoacenitrile, \u003cem\u003ep-\u003c/em\u003ebromoanisole and \u003cem\u003ep\u003c/em\u003e-bromotoluene, \u003cem\u003ep\u003c/em\u003e-bromobenzaldehyde, bromobenzene) with phenylboronic acid. The Pd\u003csup\u003eII\u003c/sup\u003e complexes (1 and 2) showed excellent activity of 87\u0026ndash;100% in these reactions. The use of \u003cem\u003ep\u003c/em\u003e-bromoacetnitrile (electron-withdrawing group) or \u003cem\u003ep\u003c/em\u003e-bromotoluene (electron-donating group) as substrates did not significantly differ in terms of catalytic activity, whether the aryl bromides used were electro-attractive or electro-absorbing. Both complexes were seen to be active catalysts in the Suzuki-Miyaura reactions (Table\u0026nbsp;\u003cspan refid=\"Tab4\" class=\"InternalRef\"\u003e4\u003c/span\u003e, entries 1 to 10).\u003c/p\u003e \u003c/div\u003e \u003c/div\u003e \u003cdiv id=\"Sec9\" class=\"Section2\"\u003e \u003ch2\u003eMizoroki-Heck coupling reaction\u003c/h2\u003e \u003cp\u003ePalladium complex (0.01 mmol), aryl halide (2 mmol), styrene (3 mmol), and K\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e (4 mmol) in ethanol/water (4 mL) were added to a two-necked round-bottomed flask containing magnetic fish for 2 h. The mixture was heated at 80\u0026deg;C using an oil bath and the progress was checked using thin layer chromatography (TLC). The mixture was extracted with ethyl acetate and passed through MgSO\u003csub\u003e4\u003c/sub\u003e to be submitted to GC-MS.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"Yes\" id=\"Tab5\" border=\"1\"\u003e \u003ccaption language=\"En\"\u003e \u003cdiv class=\"CaptionNumber\"\u003eTable 5\u003c/div\u003e \u003cdiv class=\"CaptionContent\"\u003e \u003cp\u003eMizoroki Heck coupling of styrene and aryl bromides in Pd\u003csup\u003eII\u003c/sup\u003e complexes (1 and 2)\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"6\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c6\" colnum=\"6\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003eEntry\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003ePd(II) comp.\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eAryl halide\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eTime (h)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003eTemp. (\u0026ordm;C)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c6\"\u003e \u003cp\u003eYield\u003c/p\u003e \u003cp\u003e(%)\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e\u003cem\u003ep\u003c/em\u003e-bromobenzonitrile\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e75\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e2\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e74\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e\u003cem\u003ep\u003c/em\u003e-bromobenzaldehyde\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e78\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e2\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e77\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e\u003cem\u003ep\u003c/em\u003e-bromoanisole\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e76\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e2\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e75\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e\u003cem\u003ep\u003c/em\u003e-bromotoluene\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e73\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e2\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e72\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e1\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003ebromobenzene\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003e80\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e75\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e10\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e\u003cb\u003e2\u003c/b\u003e\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c6\"\u003e \u003cp\u003e76\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e \u003cp\u003e \u003cstrong\u003eReaction conditions\u003c/strong\u003e \u003cp\u003eStyrene (3.0 mmol), aryl halide (2.0 mmol), base (4.0 mmol), catalyst (0.01 mmol), EtOH/H\u003csub\u003e2\u003c/sub\u003eO (4 mL), 2 s, 80\u0026deg;C.\u003c/p\u003e \u003c/p\u003e \u003cp\u003eIn the Mizoroki-Heck coupling reaction, good catalytic transformations ranging from 72\u0026ndash;78% were obtained in the reaction of \u003cem\u003ep\u003c/em\u003e-bromoacetonitrile with styrene as substrate (Fig.\u0026nbsp;\u003cspan refid=\"Fig4\" class=\"InternalRef\"\u003e4\u003c/span\u003e). Table\u0026nbsp;\u003cspan refid=\"Tab5\" class=\"InternalRef\"\u003e5\u003c/span\u003e shows that all bromoaryl halides used as substrates exhibited yields close to each other. It was also observed that the electronic and structural properties of the Pd\u003csup\u003eII\u003c/sup\u003e complexes used as both catalysts did not significantly affect the yields. It was observed that styrene used as olefin did not provide very high yields due to its structural properties. As a result, palladium complexes of both ligands were found to be moderate activity in Mizoroki-Heck coupling reactions. Both Pd\u003csup\u003eII\u003c/sup\u003e complexes obtained were found to be very important catalyst systems in the Mizoroki-Heck coupling reaction in terms of environmentally friendly and short reaction time compared to the literature. It is thought that the present study will lead to the creation of many novel catalyst systems.\u003c/p\u003e \u003c/div\u003e"},{"header":"Conclusion","content":"\u003cp\u003eIn the current work, both the ligands, \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e1\u003c/b\u003e\u003c/sup\u003e and \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e2\u003c/b\u003e\u003c/sup\u003e, and their complexes \u003cb\u003e1\u003c/b\u003e, \u003cb\u003e2\u003c/b\u003e have been synthesized and characterized with several analytical and spectral techniques. The conversion of the products obtained at the end of the catalytic trials was ascertained used by a GC-MS device. Based on the results of the analyses and literature studies, a square planar structure for the complexes was proposed. The catalytic activities of the synthesized complexes 1 and 2 were also tested in the Suzuki-Miyaura and Mizoroki-Heck C-C reactions. From the results of catalytic activity, the complexes 1 and 2 found to be very capable of carrying out the Suzuki-Miyaura coupling reaction. At the required reaction times, the complexes 1 and 2 were shown to undergo Suzuki cross-coupling reaction between the sterically hindered and deactivated aryl bromides and phenylbronic acid. In addition, complexes 1 and 2 showed good conversion and selectivity in short times at low catalyst loads. In the Mizoroki-Heck coupling reaction, it was observed that they provided good conversion at 72\u0026ndash;78%.\u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003e \u003ch2\u003eConflict of Interest\u003c/h2\u003e \u003cp\u003eNo conflict of interest declared\u003c/p\u003e \u003c/p\u003e\u003ch2\u003eAcknowledgment\u003c/h2\u003e \u003cp\u003eThis study was supported by Scientific Research Coordination Unit of Muş Alparslan University. Project number: BAP-22-FEF-4902-05. The authors would like thank BAP\u0026rsquo;s the financial support.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\u003cli\u003e\u003cspan\u003eAlonso F, Beletskaya IP, Yus M (2005) Non-conventional methodologies for transition-metal catalyzed carbon-carbon coupling: a critical overview. Part 1: The Heck reaction. Tetrahedron 61:11771\u0026ndash;11835. \u003cspan class=\"ExternalRef\"\u003e\u003cspan class=\"RefSource\"\u003ehttps://doi.org/10.1016/j.tet.2005.08.054\u003c/span\u003e\u003cspan address=\"10.1016/j.tet.2005.08.054\" targettype=\"DOI\" class=\"RefTarget\"\u003e\u003c/span\u003e\u003c/span\u003e\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eAmatore C, El Ka\u0026iuml;m L, Grimaud L, Jutand A, Meigni\u0026eacute; A, Romanov G (2014) Kinetic data on the synergetic role of amines and water in the reduction of phosphine-ligated palladium(II) to palladium(0). 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Arab J Chem 10:S1639\u0026ndash;S1644. \u003cspan class=\"ExternalRef\"\u003e\u003cspan class=\"RefSource\"\u003ehttps://doi.org/10.1016/j.arabjc.2013.06.006\u003c/span\u003e\u003cspan address=\"10.1016/j.arabjc.2013.06.006\" targettype=\"DOI\" class=\"RefTarget\"\u003e\u003c/span\u003e\u003c/span\u003e\u003c/span\u003e\u003c/li\u003e\u003c/ol\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":true,"highlight":"","institution":"","isAcceptedByJournal":false,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true},"keywords":"Schiff base ⸱ PdII complex ⸱ Characterization ⸱ Suzuki coupling ⸱ Heck coupling reactions","lastPublishedDoi":"10.21203/rs.3.rs-3913928/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-3913928/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eTwo Schiff base ligands, \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e1\u003c/b\u003e\u003c/sup\u003e and \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e2\u003c/b\u003e\u003c/sup\u003e, were synthesized from the reaction of 2-amino-5-ethyl-4-methylthiophene-3-carbonitrile with 2-hydroxybenzaldehyde and 4-nitrobenzaldehyde were investigated for their coordination to PdCl\u003csub\u003e2\u003c/sub\u003e(CH\u003csub\u003e3\u003c/sub\u003eCN)\u003csub\u003e2\u003c/sub\u003e. The prepared ligands \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e1\u003c/b\u003e\u003c/sup\u003e and \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e2\u003c/b\u003e\u003c/sup\u003e and the Pd\u003csup\u003eII\u003c/sup\u003e complexes 1 and 2 were characterized by using FTIR, \u003csup\u003e1\u003c/sup\u003eH, and \u003csup\u003e13\u003c/sup\u003eC NMR, UV-Vis, TGA, elemental analysis, molar conductivity, mass, and magnetic susceptibility. The characterization data agree well with the formulation of ligands \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e1\u003c/b\u003e\u003c/sup\u003e and \u003cb\u003eS\u003c/b\u003e\u003csup\u003e\u003cb\u003e2\u003c/b\u003e\u003c/sup\u003e and complexes 1 and 2. The geometries of the metal chelate were discussed with the help of magnetic and spectroscopic measurements. Finally, the catalytic potential of the synthesized Pd\u003csup\u003eII\u003c/sup\u003e complexes for Suzuki-Miyaura and Mizoroki-Heck coupling reactions was investigated using GC-MS. As a result, it was observed that the palladium complexes are the active catalysts in suitable Suzuki-Miyaura and Mizoroki-Heck C-C coupling reactions.\u003c/p\u003e","manuscriptTitle":"Synthesis, Characterization of Two New Schiff Base and Their PdII Complexes and Investigation of Palladium Catalyzed Cross-Coupling Reactions","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2024-02-28 18:56:01","doi":"10.21203/rs.3.rs-3913928/v1","editorialEvents":[{"type":"communityComments","content":0}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"14181a2f-6a53-4c1b-8692-ba39d7a69a49","owner":[],"postedDate":"February 28th, 2024","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"posted","subjectAreas":[],"tags":[],"updatedAt":"2024-03-20T07:54:10+00:00","versionOfRecord":[],"versionCreatedAt":"2024-02-28 18:56:01","video":"","vorDoi":"","vorDoiUrl":"","workflowStages":[]},"version":"v1","identity":"rs-3913928","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-3913928","identity":"rs-3913928","version":["v1"]},"buildId":"cBFmMYwuxLRRLfASyISRj","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}