Copper catalyzed carbon-selenium bond formation via the coupling reaction of aryl halides, phenylboronic acid and Se

Copper catalyzed carbon-selenium bond formation via the coupling reaction of aryl halides, phenylboronic acid and Se | 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 Article Copper catalyzed carbon-selenium bond formation via the coupling reaction of aryl halides, phenylboronic acid and Se Zeinab Shirvandi, Nadya Ghorashi, Amin Rostami This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-4742185/v1 This work is licensed under a CC BY 4.0 License Status: Published Journal Publication published 16 Apr, 2025 Read the published version in Scientific Reports → Version 1 posted 11 You are reading this latest preprint version Abstract This is the first report for C-Se bond formation involving the reaction of aryl halides with arylboronic acid and selenium powder to synthesis of unsymmetrical diaryl selenides in the presence of CuI as a homogeneous catalyst. A wide range of aryl halides react with various substituted groups under optimal conditions to provide the desired unsymmetrical diaryl selenides with good to high yields. Also, the same reactions were investigated in the presence of M-MCF@Gua-Cu as a reusable magnetic nanocatalyst under optimal conditions. The M-MCF@Gua-Cu catalyst allows for simpler (easy work-up) and greener methodology. In addition, the advantages of the presented method include the use of arylboronic acid/Se as a safe and cost-effective arylselenating system, the simplicity of operation, and green and cheap solvent. Homogeneous catalyst C–Se bond Copper complex Diaryl selenide Mesocellular silica foam Figures Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6 Figure 7 Figure 8 Figure 9 Figure 10 Figure 11 Introduction Selenium-containing compounds have received much attention due to their dual function in organic synthesis as catalysts and reaction mediators 1 , 2 . This interest extends beyond organic chemistry as these compounds show a diverse array of promising biological activities including cardiovascular disease prevention, anti-tumor and anti-viral properties, anti-oxidant effects, and anti-cancer potential. Consequently, the development of efficient synthetic methods for organoselenium compounds is of great importance (Fig. 1 ) 3 – 5 . Conventional synthetic methods for C-Se bond formation are associated with serious disadvantages such as harsh reaction conditions, toxic and polar solvents such as hexamethylphosphoric triamide (HMPA), expensive and toxic reagents, and high reaction temperature 6 , 7 . Therefore, various methods have been proposed for the production of diarylselenides 8 , 9 . Transition-metal-catalyzed carbon-heteroatom bond formation is the most efficient method for the carbon-selenium bonds formation in diaryl selenides 10 . A number of transition-metal salts and catalysts, such as Ni 11 , 12 , Pd 13 , 14 , Fe 15 , 16 , and Cu 17 , 18 , have been reported for the carbon-selenium bond formation. Also, to avoid handling unstable and foul-smelling reagents such as selenol 19 – 22 , other types of selenium compounds are used (diaryl diselenide 23 , 24 , aryl selenoate 25 and aryl selenocyanate 26 , 27 ). In 2003, the cross-coupling reaction between aryl iodides and phenylselenol in the presence of CuI as a catalyst, toluene as a solvent, and K 2 CO 3 as a base was carried out for the synthesis of diaryl selenides (Scheme 1a ) 19 . In addition, a study reported the synthesis of unsymmetrical diaryl selenides via the CuO nanocrystal-catalyzed cross-coupling reaction of aryl halides with diaryl diselenides. This method used recyclable CuO nanocrystals as catalyst in DMSO as solvent with KOH as base (Scheme 1b ) 6 . In recent years, aryl boronic acids and their derivatives have emerged as attractive building blocks for C-C and C-heteroatom bond formation due to their accessibility and stability 9 , 28 – 30 . A method for the synthesis of unsymmetric diaryl selenides via cross-coupling reactions, involving the use of arylboronic acids and diaryl diselenides with indium or iron catalysts in DMSO solvent, has been reported by Wang et al. (Scheme 1b ) 31 , 32 . Although these reagents have improved reaction conditions, they are usually prepared through laborious processes that are difficult to work with and are not suitable for sensitive functional groups 33 , 34 . This weakness limits the use of these methods for the synthesis of diaryl selenides. Another method used for the arylation of selenium in these reactions is the three-component reaction between two equivalents of an aryl halide and a selenium source. In this system, arylselenating nucleophiles are prepared from the reaction of the Se-source with an aryl halide, and following the subsequent reaction with the second aryl halide molecule, symmetrical diaryl selenides are produced 35 . Therefore, among selenium reagents, elemental selenium (or selenium powder) shows specific promise for Se-arylation due to its atom economy, low cost and stability 36 , 37 . Taniguchi described a copper-catalyzed route to symmetrical diaryl selenides using aluminum as a reductant. The reaction proceeds through the key intermediate PhSeCu, formed from the copper-catalyzed reaction of aryl iodides with selenium. Next, this intermediate proceeded via a homo-coupling reaction with aryl iodides to synthesize symmetrical diaryl selenides. (Scheme 1c ) 38 . Therefore, creating effective and simple techniques for producing unsymmetrical diaryl selenides has been considered 39 . To our understanding, the synthesis of unsymmetrical diarylselenides using aryl halides, arylboronic acid for aryl group transfer, and selenium powder as selenium donor has not been previously reported. In continuation of our studies on the synthesis of unsymmetrical diaryl selenides, herein, we report the three-component coupling of aryl halides, arylboronic acid derivatives, selenium powder and CuI as a homogeneous catalyst (Scheme 1d ). On the other hand, heterogeneous catalysts have attracted much attention due to their superior efficiency in chemical and pharmaceutical industries, important organic transformations, high yield due to phase separation and catalyst reusability 40 – 43 . In recent years, the use of mesoporous silica has become one of the most attractive catalytic supports for the heterogenization of homogeneous catalysts. Significant progress in the fabrication and analysis of these materials has led to a better understanding of their performance 44 , 45 . In comparison to other types of nanoparticles, silica mesoporous exhibit unique properties such as varying structures and relatively large pore sizes, which often give rise to improved activity and selectivity 46 , 47 . Mesocellular silica foam, also called MCF, is classified as a mesoporous material characterized by the presence of windows and cells. The spherical cells are connected by windows, resulting in a coherent and continuous three-dimensional (3D) pore system 48 – 50 . MCF has a network of pores with diameters of 20–40 nm, which are connected by windows with diameters of 10–20 nm. In addition, the specific surface area of MCF can be up to 1000 m 2 /g 51 , 52 . Also, magnetic mesocellular foam (M-MCF) can be synthesized by embedding magnetic nanoparticles (MNPs) within the porous structure of siliceous mesocellular foam, which can be easily separated and recovered in chemical reactions using an external magnetic field 53 , 54 . Also, in the continuation of this project, to investigate the synthesis of unsymmetrical diaryl selenides in the heterogeneous catalytic system, M-MCF@Gua-Cu was used as a recoverable magnetic heterogeneous nanocatalyst (Scheme 1d ). Result and discussion The preparation of M-MCF@Gua-Cu magnetic nanocatalyst was presented in Scheme 2 . After the synthesis of MCF mesoporous using the reported methods, magnetic nanoparticles were placed inside the pores of MCF silica foam. Then M-MCF nanoparticles were modified using (3-chloropropyl)trimethoxysilane and M-MCF@n-Pr-Cl nanoparticles was obtained. In the next step, M-MCF@Gua nanoparticles were obtained by immobilizing guanine as a ligand on the surface of M-MCF@n-Pr-Cl. Finally, the synthesis of M-MCF@Gua-Cu nanocatalyst was carried out by loading copper particles on the surface of M-MCF@n-Pr-Cl. The nanocatalyst was identified using SEM, EDX, HR-TEM, FT-IR, BET, VSM, AAS, XRD and TGA techniques and its catalytic activity in the synthesis of unsymmetrical diaryl selenides was investigated. Characterization of M-MCF@Gua-Cu Figure 2 shows the FT-IR spectra of the materials obtained during each step of the synthesis process for the M-MCF@Gua-Cu nanocatalyst. Absorption peaks at around 589 and 632 cm − 1 in every spectrum are attributed to the Fe-O bond, while absorption bands at approximately 455, 802, and 1083 cm − 1 are associated with Si-O-Si stretching vibrations 55 . Furthermore, the detected absorbance at 3442 cm − 1 is a result of the surface O-H groups stretching vibrations 56 . In Fig. 2 b presented, the peaks observed at 2854 and 2923 cm − 1 represent the aliphatic C-H stretching vibrations 57 . Furthermore, the presence of two peaks at 1467 cm − 1 and 1685 cm − 1 in the spectrum of M-MCF@Gua (Fig. 2 c) is indicative of C = C and C = N stretching vibrations, respectively. The bending vibrations related to C-N and N-H bonds appeared at 1371 cm − 1 and 1588 cm − 1 . Also, the absorption of 3321 cm − 1 is due to the surface stretching vibrations of N-H groups. The analysis of the M-MCF@Gua spectrum indicated that guanine was effectively fixed on the surface of M-MCF magnetic nanoparticles. In the spectrum of M-MCF@Gua-Cu (Fig. 2 d), a shift for N-H bending and stretching vibrations was observed, indicating the formation of guanine-copper complex is on the surface of M-MCF@Gua magnetic nanoparticles. As shown in Fig. 2 e, the FT-IR spectrum of the recovered M-MCF@Gua-Cu nanocatalyst shows significant similarity with the FT-IR spectrum of the fresh catalyst. These findings provide evidence that the chemical structure of the nanocatalyst remains stable during the reaction. The SEM images of the synthesized M-MCF@Gua-Cu catalyst at different scales, along with the corresponding EDX analysis, are shown in Figs. 3 and 4 . The morphology of M-MCF@Gua-Cu was observed with similar irregular spherical shapes with an average size of 15–20 nm. The presence of nitrogen, carbon, iron, silica, oxygen, and copper elements in the catalyst structure is validated by the EDX analysis, and the X-ray mapping analysis in Fig. 5 demonstrates the uniform distribution of all elements. In addition, the amount of copper loaded on the nanocatalyst surface was measured as 1.18 mmol g − 1 using atomic absorption spectroscopy. Figure 6 shows the HR-TEM images of the M-MCF before loading the copper complex. These images confirm that the MCF structure consists of spherical voids connected by "windows". Also, HR-TEM images clearly show γ-Fe 2 O 3 spherical nanoparticles as dark spots inside MCF silica pores 58 . Figure 7 shows the wide-angle XRD patterns of the synthesized M-MCF, M-MCF@Gua-Cu and recovered M-MCF@Gua-Cu. In the case of M-MCF, various diffraction peaks were observed over 2-theta at 30.4°, 35.8°, 43.5°, 54.0°, 57.5°, and 63.1°, indicating the characteristic crystalline phase of γ-Fe 2 O 3 nanoparticles (Fig. 7 a) 59 . The XRD pattern of the synthesized catalyst in Fig. 7 b shows almost the same peaks, which indicates the preservation of the structural integrity of the M-MCF upon the incorporation of the copper complex into the support. In addition, the structure of the recycled nanocatalyst was investigated using XRD analysis to compare with the fresh catalyst (Fig. 7 c). It was observed that the XRD spectra of recycled and fresh nanocatalyst are almost similar and show the same peaks. The results confirmed that the nanocatalyst retained its chemical structure throughout the recycling process. Figure 8 shows the nitrogen adsorption-sorption isotherms of M-MCF and M-MCF@Gua-Cu. The isotherms are of type IV, which showed the characteristics of mesoporous materials 60 . Table 1 documents the pore volume and the BET surface area for the M-MCF nanoparticles shown in Fig. 8 a. After loading the copper complex, most of the mesoporous pores were filled with the complex. However, the adsorption isotherm of the nanocatalyst still shows the characteristic type IV isotherm (Fig. 8 b). It is important to mention that the surface area of the nanocatalyst is often lower than the MCF surface area due to the presence of the copper complex inside the mesoporous pores. Table 1 Textural properties of M-MCF and nanocatalyst M-MCF@Gua-Cu. sample BET surface area (m 2 g − 1 ) Pore diameter by BJH method (nm) Pore volume (cm 3 g − 1 ) Window (nm) Cell (nm) M-MCF 285.95 15.01 25.85 1.01 M-MCF@Gua-Cu 144.74 10.79 12.30 0.36 The magnetic hysteresis curves of M-MCF, M-MCF@Gua-Cu and recovered M-MCF@Gua-Cu are shown in Fig. 9 . The samples exhibit typical superparamagnetic behavior. Figure 9 a and b show that the saturation magnetic values of pure M-MCF and M-MCF@Gua-Cu are 23.24 emu.g − 1 and 20.10 emu.g − 1 , respectively. These values are sufficiently high for magnetic separation with magnets. From these observations, it can be concluded that the decrease in the saturation magnetization of M-MCF@Gua-Cu is the result of the attached non-magnetic organic group, namely guanine. Then, the magnetic curve of the recovered catalyst was measured to study its structural stability under the applied conditions. As shown in Fig. 9 c, the magnetization curve of the recovered catalyst (14.94 emu.g − 1 ) is almost the same as that of the fresh catalyst. The thermal properties of M-MCF nanoparticles and M-MCF@Gua-Cu nanocatalyst were investigated by thermal analysis (TGA) in order to confirm the presence of different functional groups on the surface of nanoparticles (Fig. 10 ). As can be read from Fig. 10 a, the decrease in weight of around 1% before 190°C is due to the evaporation of moisture that is physically adsorbed. Additionally, the weight loss of approximately 3.4% between 220–550°C is attributed to the decomposition of Si-OH surface groups. The TGA curve of the nanocatalyst shows two weight loss stages, which are attributed to the loss of water and organic solvent molecules during heating up to 200°C and the decomposition of the organic groups immobilized on the M-MCF surface above 280°C (Fig. 10 b). Catalytic studies Optimization of the reaction conditions for the synthesis of diaryl selenides in the presence of a homogeneous catalyst (CuI) We started our studies to optimize the C-Se cross-coupling reaction under homogeneous conditions, and iodobenzene and phenylboronic acid were selected as model coupling partners. At first, the reaction was carried out with CuI as a homogeneous catalyst, K 2 CO 3 as a base, and selenium powder as the selenium source in DMSO solvent at 100°C (Table 2 , entry 1). Under these conditions, the reaction failed to completely produce the desired unsymmetrical diaryl selenide. Only 65% yield was observed with Na 2 CO 3 as base in this reaction (Table 2 , entry 2). Changing the base to Cs 2 CO 3 was not effective for the reaction (Table 2 , entry 3). No products were obtained using Et 3 N as the organic base (Table 2 , entry 4). KOH provided the diphenyl selenide product in good to excellent yield (Table 2 , entry 5). Also, we investigated how the amount of KOH affects this reaction (Table 2 , entry 6). The results showed that 3 mmol KOH was suitable for the desired conversion. Then we investigated the effect of different solvents, such as H 2 O, dimethylformamide (DMF), dimethyl sulfoxide (DMSO) and polyethylene glycol )PEG-200( (Table 2 , entries 7–9). Among all the tested solvents, DMSO as solvent gave a satisfying yield (Table 2 , entry 5). We then turned our attention to finding the optimal reaction temperature by adjusting it from 80 to 120°C (Table 2 , entries 10–11). Lowering the reaction temperature to 80°C resulted in a decrease of the product yield to 65% (Table 2 , entry 10), whereas a yield of 95% was achieved at 100°C (Table 2 , entry 5). It is important to mention that without a catalyst, the reaction did not take place (Table 2 , entry 12). The reaction was investigated in the presence of CuI as a homogeneous catalyst under optimal conditions (Table 2 , entry 5). In addition, the effect of other copper salts was also tested. When Cu(OAc) 2 and CuCl 2 salts were used as catalysts, 55% and 75% yields were obtained, respectively (Table 2 , entries 13–14). The amount of the catalyst was also optimized and 50 mg was obtained as the appropriate amount for the reaction (Table 2 , entries 15–17). Table 2 Screening of carbon-selenium bond formation reaction conditions using homogeneous catalyst. Entry Catalyst type amount of catalyst (mg) Solvent Base (3 mmol) Temp. (°C) Yield (%) a, b 1 CuI 50 DMSO K 2 CO 3 100 80 2 CuI 50 DMSO Na 2 CO 3 100 65 3 CuI 50 DMSO Cs 2 CO 3 100 45 4 CuI 50 DMSO Et 3 N 100 - 5 CuI 50 DMSO KOH 100 95 6 CuI 50 DMSO KOH (1.5 mmol) 100 80 7 CuI 50 H 2 O KOH reflux N.R 8 CuI 50 DMF KOH 100 55 9 CuI 50 PEG200 KOH 100 75 10 CuI 50 DMSO KOH 120 95 11 CuI 50 DMSO KOH 80 65 12 CuI - DMSO KOH 100 N.R 13 Cu(OAc) 2 50 DMSO KOH 100 55 14 CuCl 2 50 DMSO KOH 100 75 15 CuI 70 DMSO KOH 100 94 16 CuI 30 DMSO KOH 100 75 17 CuI 10 DMSO KOH 100 45 a Reaction conditions: iodobenzene (1 mmol), phenylboronic acid (1 mmol), Se (1.5 mmol), base (3 mmol), catalyst and solvent (2 mL), b Isolated yield. Having the optimal reaction conditions (Scheme 3 ), we explored the variety of aryl halides in this Cu-catalyzed cross-coupling reaction (Table 3 ). Aryl halides containing electron-donating and electron-withdrawing groups were combined with phenylboronic acid or 4-methylphenylboronic acid to produce unsymmetrical diaryl selenides with good to high yields. As expected, higher yields were obtained under optimal conditions (Table 2 , entry 5) for electron-withdrawing aryliodides than electron-donating groups. Also, the results showed that 4-methylphenylboronic acid is more reactive than phenylboronic acid. It is also observed that aryl iodides are more reactive than aryl bromides and chlorides under similar reaction conditions. The selectivity of the synthesis of unsymmetrical diaryl selenides was investigated by testing the reaction of 4-Chlorobromobenzene as a dihalogenated aryl halide. The results showed that the bromide functional group has higher reactivity (Table 3 , entry 11). Based on the results obtained (Table 2 , entries 5 and 12) and the previously reported mechanisms 35 , 61 , 62 , we have proposed a mechanism for the synthesis of unsymmetrical diaryl selenides, which is presented in Scheme 4 . We hypothesize that initially the reaction between Se and NaOH occurs and leads to the formation of sodium diselenide 63 . Then, sodium diselenide reacts with CuI to form stable copper diselenide. In the next step, the oxidative-addition reaction of copper diselenide with phenylboronic acid creates intermediate A, which is then converted to intermediate B. Then, the key intermediate C is provided by the reaction of intermediate B with aryl halides through cleavage of the C-X bond. Finally, the desired product is obtained through reductive elimination of the C intermediate, restarting the cycle. Optimization of the reaction conditions for the synthesis of diaryl selenides in the presence of a heterogeneous catalyst (M-MCF@Gua-Cu) In continuation of our research on forming C-Se bonds, we investigated synthesis of unsymmetrical diaryl selenides by reacting aryl halides with phenylboronic acid or 4-methylphenylboronic acid, Se powder, and the recoverable magnetic nanocatalyst M-MCF@Gua-Cu. Our research started by using iodobenzene and phenylboronic acid as reactants to improve the reaction parameters. (Table 4 ). To determine the amount of nanocatalyst, it was natural to try smaller amounts of catalyst. When the amount of M-MCF@Gua-Cu was decreased from 50 to 10 mg, a decrease in product yield was observed (Table 4 , entries 1–4). As a result, the amount of 30 mg was chosen as the optimal amount, and more amounts of catalyst did not significantly impact the reaction yield. Next, we examined how the solvent impacts the reaction by testing different solvents like DMF, H 2 O, DMSO, Dioxane, and PEG-200 (Table 4 , entries 5–8). When DMSO was used as the solvent, 80% product yield was observed. When the reaction was performed in PEG-200 (Table 4 , entry 3) using the same reaction conditions, the product yield increased to 94%. A significant amount of the diaryl selenide product was obtained when K 2 CO 3 was employed as the base (Table 4 , entry 10). Additionally, the product yield increased to 94% by using KOH in the reaction, while keeping other reaction conditions constant (Table 4 , entry 3). We then turned our attention to finding the optimal reaction temperature by adjusting it from 90 to 130°C (Table 4 , entries 13–14). The yield of the product decreased with decreasing reaction temperature, while a yield of 94% was obtained when the reaction was carried out at 120°C (Table 4 , entry 3). Table 4 Screening of carbon-selenium bond formation reaction conditions using heterogeneous catalyst. Entry Catalyst (mg) Solvent Base (4 mmol) Temp. (°C) Yield (%) a, b 1 - PEG200 KOH 120 N.R 2 50 PEG200 KOH 120 95 3 30 PEG200 KOH 120 94 4 10 PEG200 KOH 120 70 5 30 DMF KOH 120 65 6 30 DMSO KOH 120 80 7 30 H 2 O KOH reflux N.R 8 30 Dioxane KOH reflux N.R 9 30 PEG200 NaOH 120 70 10 30 PEG200 K 2 CO 3 120 75 11 30 PEG200 Na 2 CO 3 120 65 12 30 PEG200 KOH (2 mmol) 120 75 13 30 PEG200 KOH 130 95 14 30 PEG200 KOH 90 80 a Reaction conditions: iodobenzene (1 mmol), phenylboronic acid (1 mmol), Se (1.5 mmol), base (4 mmol), catalyst and solvent (2 mL), b Isolated yield. Under optimal conditions (Scheme 5 ), we studied the coupling reaction of different aryl halides and phenylboronic acid or 4-methylphenylboronic acid using the M-MCF@Gua-Cu magnetic nanocatalyst (Table 5 ). The corresponding diaryl selenides were synthesized with good to high yields, ranging from 70–94%, as shown in Table 5 . Among the different types of aryl halides, it is worth noting that aryl iodides show the highest levels of reactivity, as shown in Table 5 . It is interesting to observe that even aryl bromides and chlorides, which are considered to be less reactive substrates, can still be converted to the corresponding unsymmetrical diaryl selenides with good to high yields under similar reaction conditions. It was observed that aryl halides containing electron-donating groups underwent a slow conversion. Aryl halides containing electron-withdrawing groups showed good reactivity. In addition, to investigate the selectivity of this system, the reaction of dihalogenated 4-Chlorobromobenzene was studied in heterogeneous conditions. The test results showed that the bromide functional group exhibited a higher level of reactivity (Table 5 , entry 11). Reusability of the catalyst In addition to showing high catalytic performance, the cyclability of heterogeneous catalysts represents a great advantage. To achieve this, the catalytic recycling experiment was conducted using the reaction of iodobenzene and phenylboronic acid as model reactions. After each run, the nanocatalyst was recovered with a magnetic instrument, washed with ethanol, dried before use, and its efficiency was evaluated in the next step. The above procedure was repeated, finding that the nanocatalyst could be reused more than five times without significant decrease in its performance (Fig. 11 ). Conclusion In summary, a new and concise route for the synthesis of unsymmetrical diarylselenides has been developed for the first time using a copper-catalyzed three-component coupling reaction of aryl halides, phenylboronic acid, and selenium powder. One of the advantages of this method is the in site production of highly reactive aryl selenolates using arylboronic acid with selenium powder to prevent the use of selenols and diphenyl diselenides. Using CuI as a homogeneous catalyst in DMSO at 100°C, various unsymmetrical diaryl selenides were synthesized from the reaction of arylboronic acid and aryl halides containing electron-withdrawing and electron-donating groups in good to high yields. Also, we used M-MCF@Gua-Cu as a new and magnetically reusable heterogeneous nanocatalyst for the synthesis of the desired unsymmetrical diaryl selenides using this system, and all the products were obtained with good yield in a suitable reaction time. Experimental Preparation of M-MCF For the synthesis of M-MCF, in the first step, mesocellular silica foams (MCF) were synthesized using the method previously reported in the literature 64 , 65 . Then, to prepare magnetic mesocellular silica foam, magnetic nanoparticles were incorporated into the pores of MCF in the following method. Fe(NO 3 ) 3 ·9H 2 O was added to methanol solution containing 1 g of foam and subsequently subjected to drying process at 80°C. To synthesize the iron propionate complex, a mixture of propionic acid (4.6 ml) and foam impregnated with Fe(NO 3 ) 3 ·9H 2 O was stirred at 80°C for 4 h. Subsequently, the resulting composite was subjected to heat treatment at 300°C for 30 min, resulting in the production of a solid product identified as M-MCF 60 , 66 . Preparation of M-MCF@Gua-Cu Synthesis of the M-MCF@Gua-Cu nanocatalyst involved combining 1 g of M-MCF magnetic nanoparticles with 3 mL (3-chloropropyl)trimethoxysilane (CPTMS) in 30 mL of toluene under reflux conditions for 24 h. The resulting M-MCF@n-Pr-Cl was then separated using a magnetic field and dried at 50°C for 5 h. Next, M-MCF@n-Pr-Cl (1 g) and guanine (2.5 mmol) were mixed in ethanol (30 mL). This mixture was stirred at 80°C for 24 h. A magnetic field was used to separate M-MCF@Gua, after which it was washed with ethanol and dried at 60°C. Finally, the preparation of M-MCF@Gua-Cu nanocatalyst consisted of dispersing 1 g of modified M-MCF@Gua in ethanol with a volume of 30 ml. After that, the reaction mixture was stirred for 24 hours following the addition of 2.5 mmol of Cu(NO 3 ) 2 ·3H 2 O. Upon the end of the reaction, the final product was gathered with a magnet, rinsed with ethanol, and subjected to a drying process at 50°C. Preparation of diaryl selenides in the presence of a homogeneous catalyst (CuI) In the synthesis process, a 5 mL round-bottom flask was employed, which contained 2 mL of DMSO as the solvent. Then, CuI (50 mg, 25 mol%), phenylboronic acid or 4-methylphenylboronic acid (1.0 mmol), selenium powder (1.5 mmol), aryl halide (1.0 mmol), and KOH ( 3.0 mmol) were added. The mixture was stirred at 100°C and the progress of the reaction was continuously monitored by thin layer chromatography (TLC). After the reaction was finished, the catalyst underwent filtration and the mixture was subjected to extraction with ethyl acetate and water. The resulting organic layer was dried using anhydrous sodium sulfate and concentrated by evaporation of the solvent. The obtained crude material was purified via silica gel column chromatography. Finally, the desired products were obtained with a yield of 70–95%. Preparation of diaryl selenides in the presence of a heterogeneous catalyst (M-MCF@Gua-Cu) A mixture of phenylboronic acid or 4-methylphenylboronic acid (1.0 mmol), Se (1.5 mmol), aryl halides (1.0 mmol), KOH (4.0 mmol) and M-MCF@Gua-Cu (30 mg, 3.5 mol%) in 2 mL of PEG was stirred at 120°C. The reaction progress was monitored using TLC and the M-MCF@Gua-Cu nanocatalyst was magnetically removed once the reaction was complete. Next, the organic layer was separated using ethyl acetate and dehydrated with Na 2 SO 4 , followed by concentrating the solvent under reduced pressure. Finally, silica gel column chromatography using n -hexane-ethyl acetate was used to purify the products further, and pure products were obtained with a yield of 70–94%. Selected spectral data Diphenyl selenide. Oil, 1 H NMR (500 MHz, DMSO): δ (ppm) = 7.66–7.62 (m, 4 H), 7.36–7.30 (m, 6 H) (Fig. S1 ). Phenyl(p-methoxyphenyl) selenide. Oil, 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) = 7.60–7.53 (m, 4H), 7.47–7.42 (m, 2H), 7.36–7.33 (m, 1H), 7.04–6.98 (m, 2H), 3.88 (s, 3H) (Fig. S2). Di(p-tolyl) selenide. Yellow oil, 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) = 7.29 (d, J = 8.1 Hz, 4H), 7.15 (d, J = 7.8 Hz, 4H), 2.37 (s, 6H) (Fig. S3). Phenyl(p-tolyl) selenide. Yellow oil, 1 H NMR (300 MHz, CDCl 3 ): δ (ppm) = 7.46–7.42 (m, 4H), 7.29–7.25(m, 3H), 7.14 (d, J = 8.0 Hz, 2H), 2.36 (s, 3H) (Fig. S4). Declarations Acknowledgements We gratefully acknowledge the financial support of this research by the University of Kurdistan. Author contributions Zeinab Shirvandi did experimental works and manuscript draft. Nadya Ghorashi did the experimental works. Amin Rostami supervised the research project and is the corresponding author of the manuscript. Conflicts of interest There are no conflicts to declare. Data availability statement The 1 H-NMR spectra of the selected products are available in the supporting information of this article. References Reich, H. J. & Hondal, R. J. Why nature chose selenium. ACS Chem. Biol. 11 , 821-841 (2016). Kumar, S., Sharma, N., Maurya, I. K., Bhasin, A. K., Wangoo, N., Brandao, P., Félix, V., Bhasin, K. & Sharma, R. K. Facile synthesis, structural evaluation, antimicrobial activity and synergistic effects of novel imidazo [1, 2-a] pyridine based organoselenium compounds. Eur. J. Med. Chem. 123 , 916-924 (2016). Manjare, S. T., Kim, Y. & Churchill, D. G. Selenium-and tellurium-containing fluorescent molecular probes for the detection of biologically important analytes. Acc. Chem. Res. 47 , 2985-2998 (2014). Casaril, A. 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Additional Declarations No competing interests reported. Supplementary Files SupplementarymaterialSciRep.docx Scheme1.png Scheme 1. Reactions reported for the synthesis of diaryl selenides. Scheme2.png Scheme 2. Synthesis of M-MCF@Gua-Cu. Scheme3.png Scheme 3. Synthesis of diaryl selenides in the presence of a homogeneous catalyst (CuI) Scheme4.png Scheme 4. The suggested mechanism for the C-Se coupling reaction in the presence of CuI. Scheme5.png Scheme 5. Synthesis of diaryl selenides in the presence of a heterogeneous catalyst (M-MCF@Gua-Cu) Table3and5.docx Cite Share Download PDF Status: Published Journal Publication published 16 Apr, 2025 Read the published version in Scientific Reports → Version 1 posted Editorial decision: Revision requested 05 Aug, 2024 Reviewers agreed at journal 01 Aug, 2024 Reviews received at journal 23 Jul, 2024 Reviews received at journal 21 Jul, 2024 Reviewers agreed at journal 17 Jul, 2024 Reviewers agreed at journal 17 Jul, 2024 Reviewers invited by journal 17 Jul, 2024 Editor assigned by journal 17 Jul, 2024 Editor invited by journal 17 Jul, 2024 Submission checks completed at journal 16 Jul, 2024 First submitted to journal 15 Jul, 2024 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-4742185","acceptedTermsAndConditions":true,"allowDirectSubmit":false,"archivedVersions":[],"articleType":"Article","associatedPublications":[],"authors":[{"id":335924474,"identity":"7a202c5a-bbc5-4241-8244-25715d11ba04","order_by":0,"name":"Zeinab Shirvandi","email":"","orcid":"","institution":"University of Kurdistan","correspondingAuthor":false,"prefix":"","firstName":"Zeinab","middleName":"","lastName":"Shirvandi","suffix":""},{"id":335924475,"identity":"fe3314d2-b09c-44d3-99e9-ef98f94841de","order_by":1,"name":"Nadya Ghorashi","email":"","orcid":"","institution":"University of 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08:34:53","extension":"png","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":11036,"visible":true,"origin":"","legend":"\u003cp\u003eEDX spectrum of the M-MCF@Gua-Cu.\u003c/p\u003e","description":"","filename":"4.png","url":"https://assets-eu.researchsquare.com/files/rs-4742185/v1/4648e9a8967cdc5131e9b392.png"},{"id":62014345,"identity":"14fa4ac5-ccca-4c71-855c-4a1098f9c9d9","added_by":"auto","created_at":"2024-08-08 08:26:53","extension":"png","order_by":5,"title":"Figure 5","display":"","copyAsset":false,"role":"figure","size":2538116,"visible":true,"origin":"","legend":"\u003cp\u003eElemental mapping spectrum of the M-MCF@Gua-Cu.\u003c/p\u003e","description":"","filename":"5.png","url":"https://assets-eu.researchsquare.com/files/rs-4742185/v1/04c951810800c4c729be5f03.png"},{"id":62014336,"identity":"9b64c283-edda-4f5f-a95d-d400da30660b","added_by":"auto","created_at":"2024-08-08 08:26:53","extension":"png","order_by":6,"title":"Figure 6","display":"","copyAsset":false,"role":"figure","size":1631593,"visible":true,"origin":"","legend":"\u003cp\u003eHR-TEM images of M-MCF.\u003c/p\u003e","description":"","filename":"6.png","url":"https://assets-eu.researchsquare.com/files/rs-4742185/v1/a7d65b4418b27549f54e60c1.png"},{"id":62014341,"identity":"623d34fe-4763-4f0d-877a-4840f3c7d579","added_by":"auto","created_at":"2024-08-08 08:26:53","extension":"png","order_by":7,"title":"Figure 7","display":"","copyAsset":false,"role":"figure","size":178002,"visible":true,"origin":"","legend":"\u003cp\u003eNormal XRD patterns (a) M-MCF, (b) M-MCF@Gua-Cu and (c) recovered M-MCF@Gua-Cu.\u003c/p\u003e","description":"","filename":"7.png","url":"https://assets-eu.researchsquare.com/files/rs-4742185/v1/fb83aa82985288efa3a12377.png"},{"id":62014346,"identity":"09b1f531-537c-4489-8ba3-fb8f710701e3","added_by":"auto","created_at":"2024-08-08 08:26:54","extension":"png","order_by":8,"title":"Figure 8","display":"","copyAsset":false,"role":"figure","size":85057,"visible":true,"origin":"","legend":"\u003cp\u003eN\u003csub\u003e2\u003c/sub\u003e adsorption-desorption isotherms of (a) M-MCF, (b) M-MCF@Gua-Cu.\u003c/p\u003e","description":"","filename":"8.png","url":"https://assets-eu.researchsquare.com/files/rs-4742185/v1/dc1e7756ffd4acc5e74c27fd.png"},{"id":62014349,"identity":"1202c13a-1fd5-44db-bf39-cc704434e0ea","added_by":"auto","created_at":"2024-08-08 08:26:54","extension":"png","order_by":9,"title":"Figure 9","display":"","copyAsset":false,"role":"figure","size":101047,"visible":true,"origin":"","legend":"\u003cp\u003eMagnetization curves for (a) M-MCF, (b) M-MCF@Gua-Cu and (c) recovered M-MCF@Gua-Cu.\u003c/p\u003e","description":"","filename":"9.png","url":"https://assets-eu.researchsquare.com/files/rs-4742185/v1/e6e4f9e56ba1fcbd2f26ac5a.png"},{"id":62014350,"identity":"f2f7dc12-1637-497d-9e61-378b9ffea3cd","added_by":"auto","created_at":"2024-08-08 08:26:54","extension":"png","order_by":10,"title":"Figure 10","display":"","copyAsset":false,"role":"figure","size":68635,"visible":true,"origin":"","legend":"\u003cp\u003eTGA curves of (a) M-MCF, (b) M-MCF@Gua-Cu.\u003c/p\u003e","description":"","filename":"10.png","url":"https://assets-eu.researchsquare.com/files/rs-4742185/v1/696c97be4ae6f78465931d22.png"},{"id":62014348,"identity":"5cfc3d77-9fef-4169-8184-a1d30433550a","added_by":"auto","created_at":"2024-08-08 08:26:54","extension":"png","order_by":11,"title":"Figure 11","display":"","copyAsset":false,"role":"figure","size":25713,"visible":true,"origin":"","legend":"\u003cp\u003eReusability of M-MCF@Gua-Cu nanocatalyst in the reaction of iodobenzene with phenylboronic acid and Se powder.\u003c/p\u003e","description":"","filename":"11.png","url":"https://assets-eu.researchsquare.com/files/rs-4742185/v1/25b62481b8eace8945b6d886.png"},{"id":81050911,"identity":"dece50cf-3aa7-4c36-a890-808f5203b739","added_by":"auto","created_at":"2025-04-21 16:06:30","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":10189828,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-4742185/v1/68ac848c-54b4-4738-ad87-9888658e3527.pdf"},{"id":62014340,"identity":"f26fd223-a1bd-4fef-9e8c-8853107cc24e","added_by":"auto","created_at":"2024-08-08 08:26:53","extension":"docx","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":623313,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cbr\u003e\u003c/p\u003e","description":"","filename":"SupplementarymaterialSciRep.docx","url":"https://assets-eu.researchsquare.com/files/rs-4742185/v1/a522112b0a510ef53896bec2.docx"},{"id":62014343,"identity":"6717091e-1275-4bfc-a75d-5aea2b603e49","added_by":"auto","created_at":"2024-08-08 08:26:53","extension":"png","order_by":2,"title":"","display":"","copyAsset":false,"role":"supplement","size":170667,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eScheme 1. \u003c/strong\u003e\u0026nbsp;Reactions reported for the synthesis of diaryl selenides.\u003c/p\u003e","description":"","filename":"Scheme1.png","url":"https://assets-eu.researchsquare.com/files/rs-4742185/v1/07294a2ff810afa3d6d06d91.png"},{"id":62015161,"identity":"c9ad8ee4-fff9-4e8f-87f6-2ecf69f2e03c","added_by":"auto","created_at":"2024-08-08 08:34:53","extension":"png","order_by":3,"title":"","display":"","copyAsset":false,"role":"supplement","size":1204642,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eScheme 2. \u003c/strong\u003eSynthesis of M-MCF@Gua-Cu.\u003c/p\u003e","description":"","filename":"Scheme2.png","url":"https://assets-eu.researchsquare.com/files/rs-4742185/v1/4ec1650e1ab57057d3b7d203.png"},{"id":62014333,"identity":"f8618e14-2e93-4349-af11-2dfc3bc9a3e2","added_by":"auto","created_at":"2024-08-08 08:26:53","extension":"png","order_by":4,"title":"","display":"","copyAsset":false,"role":"supplement","size":19681,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eScheme 3\u003c/strong\u003e. Synthesis of diaryl selenides in the presence of a homogeneous catalyst (CuI)\u003c/p\u003e","description":"","filename":"Scheme3.png","url":"https://assets-eu.researchsquare.com/files/rs-4742185/v1/1a00f7350a81ff9ae1833664.png"},{"id":62015160,"identity":"af541527-fbae-457e-af8a-d89115843316","added_by":"auto","created_at":"2024-08-08 08:34:53","extension":"png","order_by":5,"title":"","display":"","copyAsset":false,"role":"supplement","size":42181,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eScheme 4.\u003c/strong\u003e The suggested mechanism for the C-Se coupling reaction in the presence of CuI\u003cstrong\u003e.\u003c/strong\u003e\u003c/p\u003e","description":"","filename":"Scheme4.png","url":"https://assets-eu.researchsquare.com/files/rs-4742185/v1/e8c67bc51e778e4e96dd12cd.png"},{"id":62015163,"identity":"6ce1e96c-cd3b-402f-9e0f-5040bae005e4","added_by":"auto","created_at":"2024-08-08 08:34:53","extension":"png","order_by":6,"title":"","display":"","copyAsset":false,"role":"supplement","size":18585,"visible":true,"origin":"","legend":"\u003cp\u003e\u003cstrong\u003eScheme 5\u003c/strong\u003e. Synthesis of diaryl selenides in the presence of a heterogeneous catalyst (M-MCF@Gua-Cu)\u003c/p\u003e","description":"","filename":"Scheme5.png","url":"https://assets-eu.researchsquare.com/files/rs-4742185/v1/7d91b10fd76078dd200b3fb5.png"},{"id":62015787,"identity":"af19494a-28ca-4e96-8943-4c7dc9a93348","added_by":"auto","created_at":"2024-08-08 08:42:53","extension":"docx","order_by":7,"title":"","display":"","copyAsset":false,"role":"supplement","size":175951,"visible":true,"origin":"","legend":"","description":"","filename":"Table3and5.docx","url":"https://assets-eu.researchsquare.com/files/rs-4742185/v1/c2337da2b4b59e24549a7165.docx"}],"financialInterests":"No competing interests reported.","formattedTitle":"Copper catalyzed carbon-selenium bond formation via the coupling reaction of aryl halides, phenylboronic acid and Se","fulltext":[{"header":"Introduction","content":"\u003cp\u003eSelenium-containing compounds have received much attention due to their dual function in organic synthesis as catalysts and reaction mediators \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e,\u003cspan citationid=\"CR2\" class=\"CitationRef\"\u003e2\u003c/span\u003e\u003c/sup\u003e. This interest extends beyond organic chemistry as these compounds show a diverse array of promising biological activities including cardiovascular disease prevention, anti-tumor and anti-viral properties, anti-oxidant effects, and anti-cancer potential. Consequently, the development of efficient synthetic methods for organoselenium compounds is of great importance (Fig.\u0026nbsp;\u003cspan refid=\"Fig1\" class=\"InternalRef\"\u003e1\u003c/span\u003e) \u003csup\u003e\u003cspan additionalcitationids=\"CR4\" citationid=\"CR3\" class=\"CitationRef\"\u003e3\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e5\u003c/span\u003e\u003c/sup\u003e.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eConventional synthetic methods for C-Se bond formation are associated with serious disadvantages such as harsh reaction conditions, toxic and polar solvents such as hexamethylphosphoric triamide (HMPA), expensive and toxic reagents, and high reaction temperature \u003csup\u003e\u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e6\u003c/span\u003e,\u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e7\u003c/span\u003e\u003c/sup\u003e. Therefore, various methods have been proposed for the production of diarylselenides \u003csup\u003e\u003cspan citationid=\"CR8\" class=\"CitationRef\"\u003e8\u003c/span\u003e,\u003cspan citationid=\"CR9\" class=\"CitationRef\"\u003e9\u003c/span\u003e\u003c/sup\u003e. Transition-metal-catalyzed carbon-heteroatom bond formation is the most efficient method for the carbon-selenium bonds formation in diaryl selenides \u003csup\u003e\u003cspan citationid=\"CR10\" class=\"CitationRef\"\u003e10\u003c/span\u003e\u003c/sup\u003e. A number of transition-metal salts and catalysts, such as Ni \u003csup\u003e\u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e11\u003c/span\u003e,\u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e\u003c/sup\u003e, Pd \u003csup\u003e\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e,\u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e14\u003c/span\u003e\u003c/sup\u003e, Fe \u003csup\u003e\u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e,\u003cspan citationid=\"CR16\" class=\"CitationRef\"\u003e16\u003c/span\u003e\u003c/sup\u003e, and Cu \u003csup\u003e\u003cspan citationid=\"CR17\" class=\"CitationRef\"\u003e17\u003c/span\u003e,\u003cspan citationid=\"CR18\" class=\"CitationRef\"\u003e18\u003c/span\u003e\u003c/sup\u003e, have been reported for the carbon-selenium bond formation. Also, to avoid handling unstable and foul-smelling reagents such as selenol \u003csup\u003e\u003cspan additionalcitationids=\"CR20 CR21\" citationid=\"CR19\" class=\"CitationRef\"\u003e19\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR22\" class=\"CitationRef\"\u003e22\u003c/span\u003e\u003c/sup\u003e, other types of selenium compounds are used (diaryl diselenide \u003csup\u003e\u003cspan citationid=\"CR23\" class=\"CitationRef\"\u003e23\u003c/span\u003e,\u003cspan citationid=\"CR24\" class=\"CitationRef\"\u003e24\u003c/span\u003e\u003c/sup\u003e, aryl selenoate \u003csup\u003e\u003cspan citationid=\"CR25\" class=\"CitationRef\"\u003e25\u003c/span\u003e\u003c/sup\u003e and aryl selenocyanate \u003csup\u003e\u003cspan citationid=\"CR26\" class=\"CitationRef\"\u003e26\u003c/span\u003e,\u003cspan citationid=\"CR27\" class=\"CitationRef\"\u003e27\u003c/span\u003e\u003c/sup\u003e). In 2003, the cross-coupling reaction between aryl iodides and phenylselenol in the presence of CuI as a catalyst, toluene as a solvent, and K\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e as a base was carried out for the synthesis of diaryl selenides (Scheme \u003cspan refid=\"Sch1\" class=\"InternalRef\"\u003e1a\u003c/span\u003e) \u003csup\u003e\u003cspan citationid=\"CR19\" class=\"CitationRef\"\u003e19\u003c/span\u003e\u003c/sup\u003e. In addition, a study reported the synthesis of unsymmetrical diaryl selenides \u003cem\u003evia\u003c/em\u003e the CuO nanocrystal-catalyzed cross-coupling reaction of aryl halides with diaryl diselenides. This method used recyclable CuO nanocrystals as catalyst in DMSO as solvent with KOH as base (Scheme \u003cspan refid=\"Sch1\" class=\"InternalRef\"\u003e1b\u003c/span\u003e) \u003csup\u003e\u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e6\u003c/span\u003e\u003c/sup\u003e. In recent years, aryl boronic acids and their derivatives have emerged as attractive building blocks for C-C and C-heteroatom bond formation due to their accessibility and stability \u003csup\u003e\u003cspan citationid=\"CR9\" class=\"CitationRef\"\u003e9\u003c/span\u003e,\u003cspan additionalcitationids=\"CR29\" citationid=\"CR28\" class=\"CitationRef\"\u003e28\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR30\" class=\"CitationRef\"\u003e30\u003c/span\u003e\u003c/sup\u003e. A method for the synthesis of unsymmetric diaryl selenides \u003cem\u003evia\u003c/em\u003e cross-coupling reactions, involving the use of arylboronic acids and diaryl diselenides with indium or iron catalysts in DMSO solvent, has been reported by Wang et al. (Scheme \u003cspan refid=\"Sch1\" class=\"InternalRef\"\u003e1b\u003c/span\u003e) \u003csup\u003e\u003cspan citationid=\"CR31\" class=\"CitationRef\"\u003e31\u003c/span\u003e,\u003cspan citationid=\"CR32\" class=\"CitationRef\"\u003e32\u003c/span\u003e\u003c/sup\u003e. Although these reagents have improved reaction conditions, they are usually prepared through laborious processes that are difficult to work with and are not suitable for sensitive functional groups \u003csup\u003e\u003cspan citationid=\"CR33\" class=\"CitationRef\"\u003e33\u003c/span\u003e,\u003cspan citationid=\"CR34\" class=\"CitationRef\"\u003e34\u003c/span\u003e\u003c/sup\u003e. This weakness limits the use of these methods for the synthesis of diaryl selenides. Another method used for the arylation of selenium in these reactions is the three-component reaction between two equivalents of an aryl halide and a selenium source. In this system, arylselenating nucleophiles are prepared from the reaction of the Se-source with an aryl halide, and following the subsequent reaction with the second aryl halide molecule, symmetrical diaryl selenides are produced \u003csup\u003e\u003cspan citationid=\"CR35\" class=\"CitationRef\"\u003e35\u003c/span\u003e\u003c/sup\u003e. Therefore, among selenium reagents, elemental selenium (or selenium powder) shows specific promise for Se-arylation due to its atom economy, low cost and stability \u003csup\u003e\u003cspan citationid=\"CR36\" class=\"CitationRef\"\u003e36\u003c/span\u003e,\u003cspan citationid=\"CR37\" class=\"CitationRef\"\u003e37\u003c/span\u003e\u003c/sup\u003e. Taniguchi described a copper-catalyzed route to symmetrical diaryl selenides using aluminum as a reductant. The reaction proceeds through the key intermediate PhSeCu, formed from the copper-catalyzed reaction of aryl iodides with selenium. Next, this intermediate proceeded \u003cem\u003evia\u003c/em\u003e a homo-coupling reaction with aryl iodides to synthesize symmetrical diaryl selenides. (Scheme \u003cspan refid=\"Sch1\" class=\"InternalRef\"\u003e1c\u003c/span\u003e) \u003csup\u003e\u003cspan citationid=\"CR38\" class=\"CitationRef\"\u003e38\u003c/span\u003e\u003c/sup\u003e.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eTherefore, creating effective and simple techniques for producing unsymmetrical diaryl selenides has been considered \u003csup\u003e\u003cspan citationid=\"CR39\" class=\"CitationRef\"\u003e39\u003c/span\u003e\u003c/sup\u003e. To our understanding, the synthesis of unsymmetrical diarylselenides using aryl halides, arylboronic acid for aryl group transfer, and selenium powder as selenium donor has not been previously reported. In continuation of our studies on the synthesis of unsymmetrical diaryl selenides, herein, we report the three-component coupling of aryl halides, arylboronic acid derivatives, selenium powder and CuI as a homogeneous catalyst (Scheme \u003cspan refid=\"Sch1\" class=\"InternalRef\"\u003e1d\u003c/span\u003e).\u003c/p\u003e \u003cp\u003eOn the other hand, heterogeneous catalysts have attracted much attention due to their superior efficiency in chemical and pharmaceutical industries, important organic transformations, high yield due to phase separation and catalyst reusability \u003csup\u003e\u003cspan additionalcitationids=\"CR41 CR42\" citationid=\"CR40\" class=\"CitationRef\"\u003e40\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR43\" class=\"CitationRef\"\u003e43\u003c/span\u003e\u003c/sup\u003e.\u003c/p\u003e \u003cp\u003eIn recent years, the use of mesoporous silica has become one of the most attractive catalytic supports for the heterogenization of homogeneous catalysts. Significant progress in the fabrication and analysis of these materials has led to a better understanding of their performance \u003csup\u003e\u003cspan citationid=\"CR44\" class=\"CitationRef\"\u003e44\u003c/span\u003e,\u003cspan citationid=\"CR45\" class=\"CitationRef\"\u003e45\u003c/span\u003e\u003c/sup\u003e. In comparison to other types of nanoparticles, silica mesoporous exhibit unique properties such as varying structures and relatively large pore sizes, which often give rise to improved activity and selectivity \u003csup\u003e\u003cspan citationid=\"CR46\" class=\"CitationRef\"\u003e46\u003c/span\u003e,\u003cspan citationid=\"CR47\" class=\"CitationRef\"\u003e47\u003c/span\u003e\u003c/sup\u003e. Mesocellular silica foam, also called MCF, is classified as a mesoporous material characterized by the presence of windows and cells. The spherical cells are connected by windows, resulting in a coherent and continuous three-dimensional (3D) pore system \u003csup\u003e\u003cspan additionalcitationids=\"CR49\" citationid=\"CR48\" class=\"CitationRef\"\u003e48\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR50\" class=\"CitationRef\"\u003e50\u003c/span\u003e\u003c/sup\u003e. MCF has a network of pores with diameters of 20\u0026ndash;40 nm, which are connected by windows with diameters of 10\u0026ndash;20 nm. In addition, the specific surface area of MCF can be up to 1000 m\u003csup\u003e2\u003c/sup\u003e/g \u003csup\u003e\u003cspan citationid=\"CR51\" class=\"CitationRef\"\u003e51\u003c/span\u003e,\u003cspan citationid=\"CR52\" class=\"CitationRef\"\u003e52\u003c/span\u003e\u003c/sup\u003e. Also, magnetic mesocellular foam (M-MCF) can be synthesized by embedding magnetic nanoparticles (MNPs) within the porous structure of siliceous mesocellular foam, which can be easily separated and recovered in chemical reactions using an external magnetic field \u003csup\u003e\u003cspan citationid=\"CR53\" class=\"CitationRef\"\u003e53\u003c/span\u003e,\u003cspan citationid=\"CR54\" class=\"CitationRef\"\u003e54\u003c/span\u003e\u003c/sup\u003e. Also, in the continuation of this project, to investigate the synthesis of unsymmetrical diaryl selenides in the heterogeneous catalytic system, M-MCF@Gua-Cu was used as a recoverable magnetic heterogeneous nanocatalyst (Scheme \u003cspan refid=\"Sch1\" class=\"InternalRef\"\u003e1d\u003c/span\u003e).\u003c/p\u003e"},{"header":"Result and discussion","content":"\u003cp\u003eThe preparation of M-MCF@Gua-Cu magnetic nanocatalyst was presented in Scheme \u003cspan refid=\"Sch2\" class=\"InternalRef\"\u003e2\u003c/span\u003e. After the synthesis of MCF mesoporous using the reported methods, magnetic nanoparticles were placed inside the pores of MCF silica foam. Then M-MCF nanoparticles were modified using (3-chloropropyl)trimethoxysilane and M-MCF@n-Pr-Cl nanoparticles was obtained. In the next step, M-MCF@Gua nanoparticles were obtained by immobilizing guanine as a ligand on the surface of M-MCF@n-Pr-Cl. Finally, the synthesis of M-MCF@Gua-Cu nanocatalyst was carried out by loading copper particles on the surface of M-MCF@n-Pr-Cl. The nanocatalyst was identified using SEM, EDX, HR-TEM, FT-IR, BET, VSM, AAS, XRD and TGA techniques and its catalytic activity in the synthesis of unsymmetrical diaryl selenides was investigated.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cdiv id=\"Sec3\" class=\"Section2\"\u003e \u003ch2\u003eCharacterization of M-MCF@Gua-Cu\u003c/h2\u003e \u003cp\u003eFigure\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003e shows the FT-IR spectra of the materials obtained during each step of the synthesis process for the M-MCF@Gua-Cu nanocatalyst. Absorption peaks at around 589 and 632 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e in every spectrum are attributed to the Fe-O bond, while absorption bands at approximately 455, 802, and 1083 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e are associated with Si-O-Si stretching vibrations \u003csup\u003e\u003cspan citationid=\"CR55\" class=\"CitationRef\"\u003e55\u003c/span\u003e\u003c/sup\u003e. Furthermore, the detected absorbance at 3442 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e is a result of the surface O-H groups stretching vibrations \u003csup\u003e\u003cspan citationid=\"CR56\" class=\"CitationRef\"\u003e56\u003c/span\u003e\u003c/sup\u003e. In Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003eb presented, the peaks observed at 2854 and 2923 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e represent the aliphatic C-H stretching vibrations \u003csup\u003e\u003cspan citationid=\"CR57\" class=\"CitationRef\"\u003e57\u003c/span\u003e\u003c/sup\u003e. Furthermore, the presence of two peaks at 1467 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e and 1685 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e in the spectrum of M-MCF@Gua (Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003ec) is indicative of C\u0026thinsp;=\u0026thinsp;C and C\u0026thinsp;=\u0026thinsp;N stretching vibrations, respectively. The bending vibrations related to C-N and N-H bonds appeared at 1371 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e and 1588 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e. Also, the absorption of 3321 cm\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e is due to the surface stretching vibrations of N-H groups. The analysis of the M-MCF@Gua spectrum indicated that guanine was effectively fixed on the surface of M-MCF magnetic nanoparticles. In the spectrum of M-MCF@Gua-Cu (Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003ed), a shift for N-H bending and stretching vibrations was observed, indicating the formation of guanine-copper complex is on the surface of M-MCF@Gua magnetic nanoparticles. As shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003ee, the FT-IR spectrum of the recovered M-MCF@Gua-Cu nanocatalyst shows significant similarity with the FT-IR spectrum of the fresh catalyst. These findings provide evidence that the chemical structure of the nanocatalyst remains stable during the reaction.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eThe SEM images of the synthesized M-MCF@Gua-Cu catalyst at different scales, along with the corresponding EDX analysis, are shown in Figs.\u0026nbsp;\u003cspan refid=\"Fig3\" class=\"InternalRef\"\u003e3\u003c/span\u003e and \u003cspan refid=\"Fig4\" class=\"InternalRef\"\u003e4\u003c/span\u003e. The morphology of M-MCF@Gua-Cu was observed with similar irregular spherical shapes with an average size of 15\u0026ndash;20 nm. The presence of nitrogen, carbon, iron, silica, oxygen, and copper elements in the catalyst structure is validated by the EDX analysis, and the X-ray mapping analysis in Fig.\u0026nbsp;\u003cspan refid=\"Fig5\" class=\"InternalRef\"\u003e5\u003c/span\u003e demonstrates the uniform distribution of all elements. In addition, the amount of copper loaded on the nanocatalyst surface was measured as 1.18 mmol g\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e using atomic absorption spectroscopy.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eFigure\u0026nbsp;\u003cspan refid=\"Fig6\" class=\"InternalRef\"\u003e6\u003c/span\u003e shows the HR-TEM images of the M-MCF before loading the copper complex. These images confirm that the MCF structure consists of spherical voids connected by \"windows\". Also, HR-TEM images clearly show γ-Fe\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e spherical nanoparticles as dark spots inside MCF silica pores \u003csup\u003e\u003cspan citationid=\"CR58\" class=\"CitationRef\"\u003e58\u003c/span\u003e\u003c/sup\u003e.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eFigure\u0026nbsp;\u003cspan refid=\"Fig7\" class=\"InternalRef\"\u003e7\u003c/span\u003e shows the wide-angle XRD patterns of the synthesized M-MCF, M-MCF@Gua-Cu and recovered M-MCF@Gua-Cu. In the case of M-MCF, various diffraction peaks were observed over 2-theta at 30.4\u0026deg;, 35.8\u0026deg;, 43.5\u0026deg;, 54.0\u0026deg;, 57.5\u0026deg;, and 63.1\u0026deg;, indicating the characteristic crystalline phase of γ-Fe\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e nanoparticles (Fig.\u0026nbsp;\u003cspan refid=\"Fig7\" class=\"InternalRef\"\u003e7\u003c/span\u003ea) \u003csup\u003e\u003cspan citationid=\"CR59\" class=\"CitationRef\"\u003e59\u003c/span\u003e\u003c/sup\u003e. The XRD pattern of the synthesized catalyst in Fig.\u0026nbsp;\u003cspan refid=\"Fig7\" class=\"InternalRef\"\u003e7\u003c/span\u003eb shows almost the same peaks, which indicates the preservation of the structural integrity of the M-MCF upon the incorporation of the copper complex into the support. In addition, the structure of the recycled nanocatalyst was investigated using XRD analysis to compare with the fresh catalyst (Fig.\u0026nbsp;\u003cspan refid=\"Fig7\" class=\"InternalRef\"\u003e7\u003c/span\u003ec). It was observed that the XRD spectra of recycled and fresh nanocatalyst are almost similar and show the same peaks. The results confirmed that the nanocatalyst retained its chemical structure throughout the recycling process.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eFigure\u0026nbsp;\u003cspan refid=\"Fig8\" class=\"InternalRef\"\u003e8\u003c/span\u003e shows the nitrogen adsorption-sorption isotherms of M-MCF and M-MCF@Gua-Cu. The isotherms are of type IV, which showed the characteristics of mesoporous materials \u003csup\u003e\u003cspan citationid=\"CR60\" class=\"CitationRef\"\u003e60\u003c/span\u003e\u003c/sup\u003e. Table\u0026nbsp;\u003cspan refid=\"Tab1\" class=\"InternalRef\"\u003e1\u003c/span\u003e documents the pore volume and the BET surface area for the M-MCF nanoparticles shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig8\" class=\"InternalRef\"\u003e8\u003c/span\u003ea. After loading the copper complex, most of the mesoporous pores were filled with the complex. However, the adsorption isotherm of the nanocatalyst still shows the characteristic type IV isotherm (Fig.\u0026nbsp;\u003cspan refid=\"Fig8\" class=\"InternalRef\"\u003e8\u003c/span\u003eb). It is important to mention that the surface area of the nanocatalyst is often lower than the MCF surface area due to the presence of the copper complex inside the mesoporous pores.\u003c/p\u003e \u003cp\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\u003eTextural properties of M-MCF and nanocatalyst M-MCF@Gua-Cu.\u003c/p\u003e \u003c/div\u003e \u003c/caption\u003e \u003ccolgroup cols=\"5\"\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=\"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 \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003esample\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003eBET surface area (m\u003csup\u003e\u003cspan citationid=\"CR2\" class=\"CitationRef\"\u003e2\u003c/span\u003e\u003c/sup\u003e g\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colspan=\"2\" nameend=\"c4\" namest=\"c3\"\u003e \u003cp\u003ePore diameter by BJH method (nm)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\" morerows=\"1\" rowspan=\"2\"\u003e \u003cp\u003ePore volume (cm\u003csup\u003e\u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e3\u003c/span\u003e\u003c/sup\u003e g\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e)\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003eWindow (nm)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eCell (nm)\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eM-MCF\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e285.95\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e15.01\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e25.85\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e1.01\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003eM-MCF@Gua-Cu\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e144.74\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c3\"\u003e \u003cp\u003e10.79\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c4\"\u003e \u003cp\u003e12.30\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c5\"\u003e \u003cp\u003e0.36\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\u003eThe magnetic hysteresis curves of M-MCF, M-MCF@Gua-Cu and recovered M-MCF@Gua-Cu are shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig9\" class=\"InternalRef\"\u003e9\u003c/span\u003e. The samples exhibit typical superparamagnetic behavior. Figure\u0026nbsp;\u003cspan refid=\"Fig9\" class=\"InternalRef\"\u003e9\u003c/span\u003ea and b show that the saturation magnetic values of pure M-MCF and M-MCF@Gua-Cu are 23.24 emu.g\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e and 20.10 emu.g\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e, respectively. These values are sufficiently high for magnetic separation with magnets. From these observations, it can be concluded that the decrease in the saturation magnetization of M-MCF@Gua-Cu is the result of the attached non-magnetic organic group, namely guanine. Then, the magnetic curve of the recovered catalyst was measured to study its structural stability under the applied conditions. As shown in Fig.\u0026nbsp;\u003cspan refid=\"Fig9\" class=\"InternalRef\"\u003e9\u003c/span\u003ec, the magnetization curve of the recovered catalyst (14.94 emu.g\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e) is almost the same as that of the fresh catalyst.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eThe thermal properties of M-MCF nanoparticles and M-MCF@Gua-Cu nanocatalyst were investigated by thermal analysis (TGA) in order to confirm the presence of different functional groups on the surface of nanoparticles (Fig.\u0026nbsp;\u003cspan refid=\"Fig10\" class=\"InternalRef\"\u003e10\u003c/span\u003e). As can be read from Fig.\u0026nbsp;\u003cspan refid=\"Fig10\" class=\"InternalRef\"\u003e10\u003c/span\u003ea, the decrease in weight of around 1% before 190\u0026deg;C is due to the evaporation of moisture that is physically adsorbed. Additionally, the weight loss of approximately 3.4% between 220\u0026ndash;550\u0026deg;C is attributed to the decomposition of Si-OH surface groups. The TGA curve of the nanocatalyst shows two weight loss stages, which are attributed to the loss of water and organic solvent molecules during heating up to 200\u0026deg;C and the decomposition of the organic groups immobilized on the M-MCF surface above 280\u0026deg;C (Fig.\u0026nbsp;\u003cspan refid=\"Fig10\" class=\"InternalRef\"\u003e10\u003c/span\u003eb).\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003c/div\u003e"},{"header":"Catalytic studies","content":"\u003cp\u003e\u003cstrong\u003eOptimization of the reaction conditions for the synthesis of diaryl selenides in the presence of a homogeneous catalyst (CuI)\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eWe started our studies to optimize the C-Se cross-coupling reaction under homogeneous conditions, and iodobenzene and phenylboronic acid were selected as model coupling partners. At first, the reaction was carried out with CuI as a homogeneous catalyst, K\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e as a base, and selenium powder as the selenium source in DMSO solvent at 100\u0026deg;C (Table \u003cspan\u003e2\u003c/span\u003e, entry 1). Under these conditions, the reaction failed to completely produce the desired unsymmetrical diaryl selenide. Only 65% yield was observed with Na\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e as base in this reaction (Table \u003cspan\u003e2\u003c/span\u003e, entry 2). Changing the base to Cs\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e was not effective for the reaction (Table \u003cspan\u003e2\u003c/span\u003e, entry 3). No products were obtained using Et\u003csub\u003e3\u003c/sub\u003eN as the organic base (Table \u003cspan\u003e2\u003c/span\u003e, entry 4). KOH provided the diphenyl selenide product in good to excellent yield (Table \u003cspan\u003e2\u003c/span\u003e, entry 5). Also, we investigated how the amount of KOH affects this reaction (Table \u003cspan\u003e2\u003c/span\u003e, entry 6). The results showed that 3 mmol KOH was suitable for the desired conversion. Then we investigated the effect of different solvents, such as H\u003csub\u003e2\u003c/sub\u003eO, dimethylformamide (DMF), dimethyl sulfoxide (DMSO) and polyethylene glycol )PEG-200( (Table \u003cspan\u003e2\u003c/span\u003e, entries 7\u0026ndash;9). Among all the tested solvents, DMSO as solvent gave a satisfying yield (Table \u003cspan\u003e2\u003c/span\u003e, entry 5). We then turned our attention to finding the optimal reaction temperature by adjusting it from 80 to 120\u0026deg;C (Table \u003cspan\u003e2\u003c/span\u003e, entries 10\u0026ndash;11). Lowering the reaction temperature to 80\u0026deg;C resulted in a decrease of the product yield to 65% (Table \u003cspan\u003e2\u003c/span\u003e, entry 10), whereas a yield of 95% was achieved at 100\u0026deg;C (Table \u003cspan\u003e2\u003c/span\u003e, entry 5). It is important to mention that without a catalyst, the reaction did not take place (Table \u003cspan\u003e2\u003c/span\u003e, entry 12). The reaction was investigated in the presence of CuI as a homogeneous catalyst under optimal conditions (Table \u003cspan\u003e2\u003c/span\u003e, entry 5). In addition, the effect of other copper salts was also tested. When Cu(OAc)\u003csub\u003e2\u003c/sub\u003e and CuCl\u003csub\u003e2\u003c/sub\u003e salts were used as catalysts, 55% and 75% yields were obtained, respectively (Table \u003cspan\u003e2\u003c/span\u003e, entries 13\u0026ndash;14). The amount of the catalyst was also optimized and 50 mg was obtained as the appropriate amount for the reaction (Table \u003cspan\u003e2\u003c/span\u003e, entries 15\u0026ndash;17).\u003c/p\u003e\n\u003cdiv\u003e\n \u003ctable id=\"Tab2\" border=\"1\"\u003e\n \u003ccaption language=\"En\"\u003e\n \u003cdiv\u003eTable 2\u003c/div\u003e\n \u003cdiv\u003e\n \u003cp\u003eScreening of carbon-selenium bond formation reaction conditions using homogeneous catalyst.\u003c/p\u003e\n \u003c/div\u003e\n \u003c/caption\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eEntry\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eCatalyst type\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eamount of catalyst (mg)\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eSolvent\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eBase (3 mmol)\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eTemp. (\u0026deg;C)\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eYield (%)\u003csup\u003ea, b\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCuI\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMSO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eK\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e80\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCuI\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMSO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eNa\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e65\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCuI\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMSO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCs\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e45\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCuI\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMSO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eEt\u003csub\u003e3\u003c/sub\u003eN\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCuI\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMSO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e95\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCuI\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMSO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH (1.5 mmol)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e80\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCuI\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eH\u003csub\u003e2\u003c/sub\u003eO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ereflux\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eN.R\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCuI\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMF\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e55\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCuI\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePEG200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e75\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCuI\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMSO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e120\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e95\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e11\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCuI\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMSO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e80\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e65\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e12\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCuI\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMSO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eN.R\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e13\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCu(OAc)\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMSO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e55\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e14\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCuCl\u003csub\u003e2\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMSO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e75\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e15\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCuI\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e70\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMSO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e94\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e16\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCuI\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMSO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e75\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e17\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eCuI\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMSO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e100\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e45\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003c/table\u003e\n\u003c/div\u003e\n\u003cp\u003e\u003csup\u003ea\u003c/sup\u003e Reaction conditions: iodobenzene (1 mmol), phenylboronic acid (1 mmol), Se (1.5 mmol), base (3 mmol), catalyst and solvent (2 mL), \u003csup\u003eb\u003c/sup\u003e Isolated yield.\u003c/p\u003e\n\u003cp\u003eHaving the optimal reaction conditions (Scheme \u003cspan\u003e3\u003c/span\u003e), we explored the variety of aryl halides in this Cu-catalyzed cross-coupling reaction (Table \u003cspan\u003e3\u003c/span\u003e). Aryl halides containing electron-donating and electron-withdrawing groups were combined with phenylboronic acid or 4-methylphenylboronic acid to produce unsymmetrical diaryl selenides with good to high yields. As expected, higher yields were obtained under optimal conditions (Table \u003cspan\u003e2\u003c/span\u003e, entry 5) for electron-withdrawing aryliodides than electron-donating groups. Also, the results showed that 4-methylphenylboronic acid is more reactive than phenylboronic acid. It is also observed that aryl iodides are more reactive than aryl bromides and chlorides under similar reaction conditions. The selectivity of the synthesis of unsymmetrical diaryl selenides was investigated by testing the reaction of 4-Chlorobromobenzene as a dihalogenated aryl halide. The results showed that the bromide functional group has higher reactivity (Table \u003cspan\u003e3\u003c/span\u003e, entry 11).\u003c/p\u003e\n\u003cdiv\u003eBased on the results obtained (Table \u003cspan\u003e2\u003c/span\u003e, entries 5 and 12) and the previously reported mechanisms \u003csup\u003e\u003cspan\u003e35\u003c/span\u003e,\u003cspan\u003e61\u003c/span\u003e,\u003cspan\u003e62\u003c/span\u003e\u003c/sup\u003e, we have proposed a mechanism for the synthesis of unsymmetrical diaryl selenides, which is presented in Scheme \u003cspan\u003e4\u003c/span\u003e. We hypothesize that initially the reaction between Se and NaOH occurs and leads to the formation of sodium diselenide \u003csup\u003e\u003cspan\u003e63\u003c/span\u003e\u003c/sup\u003e. Then, sodium diselenide reacts with CuI to form stable copper diselenide. In the next step, the oxidative-addition reaction of copper diselenide with phenylboronic acid creates intermediate A, which is then converted to intermediate B. Then, the key intermediate C is provided by the reaction of intermediate B with aryl halides through cleavage of the C-X bond. Finally, the desired product is obtained through reductive elimination of the C intermediate, restarting the cycle.\u003c/div\u003e\n\u003cp\u003e\u003cstrong\u003eOptimization of the reaction conditions for the synthesis of diaryl selenides in the presence of a heterogeneous catalyst (M-MCF@Gua-Cu)\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eIn continuation of our research on forming C-Se bonds, we investigated synthesis of unsymmetrical diaryl selenides by reacting aryl halides with phenylboronic acid or 4-methylphenylboronic acid, Se powder, and the recoverable magnetic nanocatalyst M-MCF@Gua-Cu. Our research started by using iodobenzene and phenylboronic acid as reactants to improve the reaction parameters. (Table \u003cspan\u003e4\u003c/span\u003e). To determine the amount of nanocatalyst, it was natural to try smaller amounts of catalyst. When the amount of M-MCF@Gua-Cu was decreased from 50 to 10 mg, a decrease in product yield was observed (Table \u003cspan\u003e4\u003c/span\u003e, entries 1\u0026ndash;4). As a result, the amount of 30 mg was chosen as the optimal amount, and more amounts of catalyst did not significantly impact the reaction yield. Next, we examined how the solvent impacts the reaction by testing different solvents like DMF, H\u003csub\u003e2\u003c/sub\u003eO, DMSO, Dioxane, and PEG-200 (Table \u003cspan\u003e4\u003c/span\u003e, entries 5\u0026ndash;8). When DMSO was used as the solvent, 80% product yield was observed. When the reaction was performed in PEG-200 (Table \u003cspan\u003e4\u003c/span\u003e, entry 3) using the same reaction conditions, the product yield increased to 94%. A significant amount of the diaryl selenide product was obtained when K\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e was employed as the base (Table \u003cspan\u003e4\u003c/span\u003e, entry 10). Additionally, the product yield increased to 94% by using KOH in the reaction, while keeping other reaction conditions constant (Table \u003cspan\u003e4\u003c/span\u003e, entry 3). We then turned our attention to finding the optimal reaction temperature by adjusting it from 90 to 130\u0026deg;C (Table \u003cspan\u003e4\u003c/span\u003e, entries 13\u0026ndash;14). The yield of the product decreased with decreasing reaction temperature, while a yield of 94% was obtained when the reaction was carried out at 120\u0026deg;C (Table \u003cspan\u003e4\u003c/span\u003e, entry 3).\u003c/p\u003e\n\u003cdiv\u003e\n \u003ctable id=\"Tab4\" border=\"1\"\u003e\n \u003ccaption language=\"En\"\u003e\n \u003cdiv\u003eTable 4\u003c/div\u003e\n \u003cdiv\u003e\n \u003cp\u003eScreening of carbon-selenium bond formation reaction conditions using heterogeneous catalyst.\u003c/p\u003e\n \u003c/div\u003e\n \u003c/caption\u003e\n \u003cthead\u003e\n \u003ctr\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eEntry\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eCatalyst (mg)\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eSolvent\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eBase (4 mmol)\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eTemp. (\u0026deg;C)\u003c/p\u003e\n \u003c/th\u003e\n \u003cth align=\"left\"\u003e\n \u003cp\u003eYield (%)\u003csup\u003ea, b\u003c/sup\u003e\u003c/p\u003e\n \u003c/th\u003e\n \u003c/tr\u003e\n \u003c/thead\u003e\n \u003ctbody\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e1\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e-\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePEG200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e120\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eN.R\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e2\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e50\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePEG200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e120\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e95\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e3\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePEG200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e120\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e94\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e4\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePEG200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e120\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e70\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e5\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMF\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e120\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e65\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e6\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDMSO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e120\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e80\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e7\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eH\u003csub\u003e2\u003c/sub\u003eO\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ereflux\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eN.R\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e8\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eDioxane\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ereflux\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eN.R\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e9\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePEG200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eNaOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e120\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e70\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e10\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePEG200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eK\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e120\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e75\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e11\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePEG200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eNa\u003csub\u003e2\u003c/sub\u003eCO\u003csub\u003e3\u003c/sub\u003e\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e120\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e65\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e12\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePEG200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH (2 mmol)\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e120\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e75\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e13\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePEG200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e130\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e95\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003ctr\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e14\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e30\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003ePEG200\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003eKOH\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e90\u003c/p\u003e\n \u003c/td\u003e\n \u003ctd align=\"left\"\u003e\n \u003cp\u003e80\u003c/p\u003e\n \u003c/td\u003e\n \u003c/tr\u003e\n \u003c/tbody\u003e\n \u003c/table\u003e\n\u003c/div\u003e\n\u003cdiv\u003e\n \u003cp\u003e\u003csup\u003ea\u003c/sup\u003e Reaction conditions: iodobenzene (1 mmol), phenylboronic acid (1 mmol), Se (1.5 mmol), base (4 mmol), catalyst and solvent (2 mL), \u003csup\u003eb\u003c/sup\u003e Isolated yield.\u003c/p\u003e\n\u003c/div\u003e\n\u003cp\u003eUnder optimal conditions (Scheme \u003cspan\u003e5\u003c/span\u003e), we studied the coupling reaction of different aryl halides and phenylboronic acid or 4-methylphenylboronic acid using the M-MCF@Gua-Cu magnetic nanocatalyst (Table \u003cspan\u003e5\u003c/span\u003e). The corresponding diaryl selenides were synthesized with good to high yields, ranging from 70\u0026ndash;94%, as shown in Table \u003cspan\u003e5\u003c/span\u003e. Among the different types of aryl halides, it is worth noting that aryl iodides show the highest levels of reactivity, as shown in Table \u003cspan\u003e5\u003c/span\u003e. It is interesting to observe that even aryl bromides and chlorides, which are considered to be less reactive substrates, can still be converted to the corresponding unsymmetrical diaryl selenides with good to high yields under similar reaction conditions. It was observed that aryl halides containing electron-donating groups underwent a slow conversion. Aryl halides containing electron-withdrawing groups showed good reactivity. In addition, to investigate the selectivity of this system, the reaction of dihalogenated 4-Chlorobromobenzene was studied in heterogeneous conditions. The test results showed that the bromide functional group exhibited a higher level of reactivity (Table \u003cspan\u003e5\u003c/span\u003e, entry 11).\u003c/p\u003e\n\u003cdiv id=\"Sec5\"\u003e\n \u003ch2\u003eReusability of the catalyst\u003c/h2\u003e\n \u003cp\u003eIn addition to showing high catalytic performance, the cyclability of heterogeneous catalysts represents a great advantage. To achieve this, the catalytic recycling experiment was conducted using the reaction of iodobenzene and phenylboronic acid as model reactions. After each run, the nanocatalyst was recovered with a magnetic instrument, washed with ethanol, dried before use, and its efficiency was evaluated in the next step. The above procedure was repeated, finding that the nanocatalyst could be reused more than five times without significant decrease in its performance (Fig. \u003cspan\u003e11\u003c/span\u003e).\u003c/p\u003e\n\u003c/div\u003e"},{"header":"Conclusion","content":"\u003cp\u003eIn summary, a new and concise route for the synthesis of unsymmetrical diarylselenides has been developed for the first time using a copper-catalyzed three-component coupling reaction of aryl halides, phenylboronic acid, and selenium powder. One of the advantages of this method is the in site production of highly reactive aryl selenolates using arylboronic acid with selenium powder to prevent the use of selenols and diphenyl diselenides. Using CuI as a homogeneous catalyst in DMSO at 100\u0026deg;C, various unsymmetrical diaryl selenides were synthesized from the reaction of arylboronic acid and aryl halides containing electron-withdrawing and electron-donating groups in good to high yields. Also, we used M-MCF@Gua-Cu as a new and magnetically reusable heterogeneous nanocatalyst for the synthesis of the desired unsymmetrical diaryl selenides using this system, and all the products were obtained with good yield in a suitable reaction time.\u003c/p\u003e"},{"header":"Experimental","content":"\u003cp\u003e \u003cb\u003ePreparation of M-MCF\u003c/b\u003e \u003c/p\u003e \u003cp\u003eFor the synthesis of M-MCF, in the first step, mesocellular silica foams (MCF) were synthesized using the method previously reported in the literature \u003csup\u003e\u003cspan citationid=\"CR64\" class=\"CitationRef\"\u003e64\u003c/span\u003e,\u003cspan citationid=\"CR65\" class=\"CitationRef\"\u003e65\u003c/span\u003e\u003c/sup\u003e. Then, to prepare magnetic mesocellular silica foam, magnetic nanoparticles were incorporated into the pores of MCF in the following method. Fe(NO\u003csub\u003e3\u003c/sub\u003e)\u003csub\u003e3\u003c/sub\u003e\u0026middot;9H\u003csub\u003e2\u003c/sub\u003eO was added to methanol solution containing 1 g of foam and subsequently subjected to drying process at 80\u0026deg;C. To synthesize the iron propionate complex, a mixture of propionic acid (4.6 ml) and foam impregnated with Fe(NO\u003csub\u003e3\u003c/sub\u003e)\u003csub\u003e3\u003c/sub\u003e\u0026middot;9H\u003csub\u003e2\u003c/sub\u003eO was stirred at 80\u0026deg;C for 4 h. Subsequently, the resulting composite was subjected to heat treatment at 300\u0026deg;C for 30 min, resulting in the production of a solid product identified as M-MCF \u003csup\u003e\u003cspan citationid=\"CR60\" class=\"CitationRef\"\u003e60\u003c/span\u003e,\u003cspan citationid=\"CR66\" class=\"CitationRef\"\u003e66\u003c/span\u003e\u003c/sup\u003e.\u003c/p\u003e \u003cp\u003e \u003cb\u003ePreparation of M-MCF@Gua-Cu\u003c/b\u003e \u003c/p\u003e \u003cp\u003eSynthesis of the M-MCF@Gua-Cu nanocatalyst involved combining 1 g of M-MCF magnetic nanoparticles with 3 mL (3-chloropropyl)trimethoxysilane (CPTMS) in 30 mL of toluene under reflux conditions for 24 h. The resulting M-MCF@n-Pr-Cl was then separated using a magnetic field and dried at 50\u0026deg;C for 5 h. Next, M-MCF@n-Pr-Cl (1 g) and guanine (2.5 mmol) were mixed in ethanol (30 mL). This mixture was stirred at 80\u0026deg;C for 24 h. A magnetic field was used to separate M-MCF@Gua, after which it was washed with ethanol and dried at 60\u0026deg;C. Finally, the preparation of M-MCF@Gua-Cu nanocatalyst consisted of dispersing 1 g of modified M-MCF@Gua in ethanol with a volume of 30 ml. After that, the reaction mixture was stirred for 24 hours following the addition of 2.5 mmol of Cu(NO\u003csub\u003e3\u003c/sub\u003e)\u003csub\u003e2\u003c/sub\u003e\u0026middot;3H\u003csub\u003e2\u003c/sub\u003eO. Upon the end of the reaction, the final product was gathered with a magnet, rinsed with ethanol, and subjected to a drying process at 50\u0026deg;C.\u003c/p\u003e \u003cdiv id=\"Sec8\" class=\"Section2\"\u003e \u003ch2\u003ePreparation of diaryl selenides in the presence of a homogeneous catalyst (CuI)\u003c/h2\u003e \u003cp\u003eIn the synthesis process, a 5 mL round-bottom flask was employed, which contained 2 mL of DMSO as the solvent. Then, CuI (50 mg, 25 mol%), phenylboronic acid or 4-methylphenylboronic acid (1.0 mmol), selenium powder (1.5 mmol), aryl halide (1.0 mmol), and KOH ( 3.0 mmol) were added. The mixture was stirred at 100\u0026deg;C and the progress of the reaction was continuously monitored by thin layer chromatography (TLC). After the reaction was finished, the catalyst underwent filtration and the mixture was subjected to extraction with ethyl acetate and water. The resulting organic layer was dried using anhydrous sodium sulfate and concentrated by evaporation of the solvent. The obtained crude material was purified \u003cem\u003evia\u003c/em\u003e silica gel column chromatography. Finally, the desired products were obtained with a yield of 70\u0026ndash;95%.\u003c/p\u003e \u003cp\u003e \u003cb\u003ePreparation of diaryl selenides in the presence of a heterogeneous catalyst (M-MCF@Gua-Cu)\u003c/b\u003e \u003c/p\u003e \u003cp\u003eA mixture of phenylboronic acid or 4-methylphenylboronic acid (1.0 mmol), Se (1.5 mmol), aryl halides (1.0 mmol), KOH (4.0 mmol) and M-MCF@Gua-Cu (30 mg, 3.5 mol%) in 2 mL of PEG was stirred at 120\u0026deg;C. The reaction progress was monitored using TLC and the M-MCF@Gua-Cu nanocatalyst was magnetically removed once the reaction was complete. Next, the organic layer was separated using ethyl acetate and dehydrated with Na\u003csub\u003e2\u003c/sub\u003eSO\u003csub\u003e4\u003c/sub\u003e, followed by concentrating the solvent under reduced pressure. Finally, silica gel column chromatography using \u003cem\u003en\u003c/em\u003e-hexane-ethyl acetate was used to purify the products further, and pure products were obtained with a yield of 70\u0026ndash;94%.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec9\" class=\"Section2\"\u003e \u003ch2\u003eSelected spectral data\u003c/h2\u003e \u003cp\u003e \u003cb\u003eDiphenyl selenide.\u003c/b\u003e Oil, \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eH NMR (500 MHz, DMSO): \u003cem\u003eδ\u003c/em\u003e (ppm)\u0026thinsp;=\u0026thinsp;7.66\u0026ndash;7.62 (m, 4 H), 7.36\u0026ndash;7.30 (m, 6 H) (Fig. \u003cspan refid=\"MOESM1\" class=\"InternalRef\"\u003eS1\u003c/span\u003e).\u003c/p\u003e \u003cp\u003e \u003cb\u003ePhenyl(p-methoxyphenyl) selenide.\u003c/b\u003e Oil, \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eH NMR (300 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e): \u003cem\u003eδ\u003c/em\u003e (ppm)\u0026thinsp;=\u0026thinsp;7.60\u0026ndash;7.53 (m, 4H), 7.47\u0026ndash;7.42 (m, 2H), 7.36\u0026ndash;7.33 (m, 1H), 7.04\u0026ndash;6.98 (m, 2H), 3.88 (s, 3H) (Fig. S2).\u003c/p\u003e \u003cp\u003e \u003cb\u003eDi(p-tolyl) selenide.\u003c/b\u003e Yellow oil, \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eH NMR (300 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e): \u003cem\u003eδ\u003c/em\u003e (ppm)\u0026thinsp;=\u0026thinsp;7.29 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.1 Hz, 4H), 7.15 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.8 Hz, 4H), 2.37 (s, 6H) (Fig. S3).\u003c/p\u003e \u003cp\u003e \u003cb\u003ePhenyl(p-tolyl) selenide.\u003c/b\u003e Yellow oil, \u003csup\u003e\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u003c/sup\u003eH NMR (300 MHz, CDCl\u003csub\u003e3\u003c/sub\u003e): \u003cem\u003eδ\u003c/em\u003e (ppm)\u0026thinsp;=\u0026thinsp;7.46\u0026ndash;7.42 (m, 4H), 7.29\u0026ndash;7.25(m, 3H), 7.14 (d, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;8.0 Hz, 2H), 2.36 (s, 3H) (Fig. S4).\u003c/p\u003e \u003c/div\u003e"},{"header":"Declarations","content":"\u003cp\u003e\u003cstrong\u003eAcknowledgements\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eWe gratefully acknowledge the financial support of this research by the University of Kurdistan.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAuthor\u003c/strong\u003e\u003cstrong\u003e\u0026nbsp;contributions\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eZeinab Shirvandi did experimental works and manuscript draft.\u0026nbsp;Nadya Ghorashi\u003csup\u003e\u0026nbsp;\u003c/sup\u003edid the experimental works. Amin Rostami supervised the research project and is the corresponding author of the manuscript.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eConflicts of interest\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThere are no conflicts to declare.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eData availability statement\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe \u003csup\u003e1\u003c/sup\u003eH-NMR spectra of the selected products are available in the supporting information of this article.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\n\u003cli\u003eReich, H. J. \u0026amp; Hondal, R. J. Why nature chose selenium. \u003cem\u003eACS Chem. Biol.\u003c/em\u003e \u003cstrong\u003e11\u003c/strong\u003e, 821-841 (2016).\u003c/li\u003e\n\u003cli\u003eKumar, S., Sharma, N., Maurya, I. K., Bhasin, A. K., Wangoo, N., Brandao, P., F\u0026eacute;lix, V., Bhasin, K. \u0026amp; Sharma, R. K. 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Chem.\u003c/em\u003e \u003cstrong\u003e34\u003c/strong\u003e, e5899 (2020).\u003c/li\u003e\n\u003c/ol\u003e"},{"header":"Table 3 and 5","content":"\u003cp\u003eTable 3 and 5 are available in the Supplementary Files section.\u003c/p\u003e"},{"header":"Schemes ","content":"\u003cp\u003eSchemes are available in the Supplementary Files section.\u003c/p\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":false,"highlight":"","institution":"","isAcceptedByJournal":true,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"scientific-reports","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"scirep","sideBox":"Learn more about [Scientific Reports](http://www.nature.com/srep/)","snPcode":"","submissionUrl":"","title":"Scientific Reports","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"stoa","reportingPortfolio":"Scientific Reports","inReviewEnabled":true,"inReviewRevisionsEnabled":true},"keywords":"Homogeneous catalyst, C–Se bond, Copper complex, Diaryl selenide, Mesocellular silica foam","lastPublishedDoi":"10.21203/rs.3.rs-4742185/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-4742185/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eThis is the first report for C-Se bond formation involving the reaction of aryl halides with arylboronic acid and selenium powder to synthesis of unsymmetrical diaryl selenides in the presence of CuI as a homogeneous catalyst. A wide range of aryl halides react with various substituted groups under optimal conditions to provide the desired unsymmetrical diaryl selenides with good to high yields. Also, the same reactions were investigated in the presence of M-MCF@Gua-Cu as a reusable magnetic nanocatalyst under optimal conditions. The M-MCF@Gua-Cu catalyst allows for simpler (easy work-up) and greener methodology. In addition, the advantages of the presented method include the use of arylboronic acid/Se as a safe and cost-effective arylselenating system, the simplicity of operation, and green and cheap solvent.\u003c/p\u003e","manuscriptTitle":"Copper catalyzed carbon-selenium bond formation via the coupling reaction of aryl halides, phenylboronic acid and Se","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2024-08-08 08:26:48","doi":"10.21203/rs.3.rs-4742185/v1","editorialEvents":[{"type":"communityComments","content":0},{"type":"decision","content":"Revision requested","date":"2024-08-05T05:22:05+00:00","index":"","fulltext":""},{"type":"reviewerAgreed","content":"32474553625987958805928130066605379997","date":"2024-08-01T13:52:55+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2024-07-23T20:05:09+00:00","index":"hide","fulltext":""},{"type":"editorInvitedReview","content":"","date":"2024-07-21T18:14:27+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"300536089575101525797036692874858517472","date":"2024-07-18T01:55:54+00:00","index":"hide","fulltext":""},{"type":"reviewerAgreed","content":"304294691995397479987867989115329106964","date":"2024-07-17T23:49:32+00:00","index":"hide","fulltext":""},{"type":"reviewersInvited","content":"","date":"2024-07-17T19:54:22+00:00","index":"","fulltext":""},{"type":"editorAssigned","content":"","date":"2024-07-17T19:52:55+00:00","index":"","fulltext":""},{"type":"editorInvited","content":"","date":"2024-07-17T17:43:02+00:00","index":"","fulltext":""},{"type":"checksComplete","content":"","date":"2024-07-16T07:09:03+00:00","index":"","fulltext":""},{"type":"submitted","content":"Scientific Reports","date":"2024-07-15T10:30:09+00:00","index":"","fulltext":""}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"scientific-reports","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":false,"externalIdentity":"scirep","sideBox":"Learn more about [Scientific Reports](http://www.nature.com/srep/)","snPcode":"","submissionUrl":"","title":"Scientific Reports","twitterHandle":"","acdcEnabled":true,"dfaEnabled":true,"editorialSystem":"stoa","reportingPortfolio":"Scientific Reports","inReviewEnabled":true,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"39230daf-e52b-48de-b213-cf9de4c3a924","owner":[],"postedDate":"August 8th, 2024","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"published-in-journal","subjectAreas":[],"tags":[],"updatedAt":"2025-04-21T16:01:41+00:00","versionOfRecord":{"articleIdentity":"rs-4742185","link":"https://doi.org/10.1038/s41598-025-96747-4","journal":{"identity":"scientific-reports","isVorOnly":false,"title":"Scientific Reports"},"publishedOn":"2025-04-16 15:57:48","publishedOnDateReadable":"April 16th, 2025"},"versionCreatedAt":"2024-08-08 08:26:48","video":"","vorDoi":"10.1038/s41598-025-96747-4","vorDoiUrl":"https://doi.org/10.1038/s41598-025-96747-4","workflowStages":[]},"version":"v1","identity":"rs-4742185","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-4742185","identity":"rs-4742185","version":["v1"]},"buildId":"qtupq5eGEP_6zYnWcrvyt","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}