Divergent Synthesis of 3-Trifluoroethyl Benzofurans through Rh-Catalyzed C−C bond Activation Coupled with Transfer Hydrogenation

Divergent Synthesis of 3-Trifluoroethyl Benzofurans through Rh-Catalyzed C−C bond Activation Coupled with Transfer Hydrogenation | Authorea try { document.documentElement.classList.add('js'); } catch (e) { } var _gaq = _gaq || []; _gaq.push(['_setAccount', 'G-8VDV14Y67G']); _gaq.push(['_trackPageview']); (function() { var ga = document.createElement('script'); ga.type = 'text/javascript'; ga.async = true; ga.src = ('https:' == document.location.protocol ? 'https://ssl' : 'http://www') + '.google-analytics.com/ga.js'; var s = document.getElementsByTagName('script')[0]; s.parentNode.insertBefore(ga, s); })(); Skip to main content Preprints Collections Wiley Open Research IET Open Research Ecological Society of Japan All Collections About About Authorea FAQs Contact Us Quick Search anywhere Search for preprint articles, keywords, etc. Search Search ADVANCED SEARCH SCROLL This is a preprint and has not been peer reviewed. Data may be preliminary. 9 April 2025 V1 Latest version Share on Divergent Synthesis of 3-Trifluoroethyl Benzofurans through Rh-Catalyzed C−C bond Activation Coupled with Transfer Hydrogenation Authors : Qi Tang , Qi Wang , Li-Juan Zhang , Bi-Qin Wang , Hai-Liang Ni , and Feijie Song [email protected] Authors Info & Affiliations https://doi.org/10.22541/au.174417327.72839324/v1 112 views 83 downloads Contents Abstract Supplementary Material Information & Authors Metrics & Citations View Options References Figures Tables Media Share Abstract not-yet-known not-yet-known not-yet-known unknown Text：The strategic incorporation of the pharmacologically privileged trifluoroethyl group into the biologically significant benzofuran scaffold offers considerable potential for medicinal and agrochemical applications. Herein, we report an atom-economical synthetic approach to 3-trifluoroethyl benzofurans through Rh-catalyzed cascade reaction of readily available trifluoromethyl alkene-tethered benzocyclobutenols. This transformation proceeds via a mechanistically intricate sequence involving C−C bond activation, migratory insertion, β-hydride elimination, chain walking, and transfer hydrogenation. A key challenge in this process, namely the selective β-H elimination of α-trifluoromethyl alkylrhodium species with the suppression of the β-F elimination, has been addressed through transfer hydrogenation strategy. By modulation of reaction conditions, both intermolecular and intramolecular transfer hydrogenation pathways have been developed, leading to the divergent synthesis of 4-β-keto and 4-β-hydroxy substituted 3-trifluoroethyl benzofurans. To our knowledge, this work represents the first general and practical synthetic method for 3-trifluoroethyl benzofurans. Supplementary Material File (song-manuscript-final.doc) Download 1.48 MB Information & Authors Information Version history V1 Version 1 09 April 2025 Copyright This work is licensed under a Non Exclusive No Reuse License. Keywords 3-trifluoroethylbenzofurans benzocyclobutenol c−c bond activation heck-type reaction transfer hydrogenation trifluoromethyl alkene Authors Affiliations Qi Tang Sichuan Normal University View all articles by this author Qi Wang Sichuan Normal University View all articles by this author Li-Juan Zhang Sichuan Normal University View all articles by this author Bi-Qin Wang Sichuan Normal University View all articles by this author Hai-Liang Ni Sichuan Normal University View all articles by this author Feijie Song [email protected] Sichuan Normal University View all articles by this author Metrics & Citations Metrics Article Usage 112 views 83 downloads .FvxKWukQNSOunydq8rnd { width: 100px; } Citations Download citation Qi Tang, Qi Wang, Li-Juan Zhang, et al. Divergent Synthesis of 3-Trifluoroethyl Benzofurans through Rh-Catalyzed C−C bond Activation Coupled with Transfer Hydrogenation. Authorea . 09 April 2025. DOI: https://doi.org/10.22541/au.174417327.72839324/v1 If you have the appropriate software installed, you can download article citation data to the citation manager of your choice. Simply select your manager software from the list below and click Download. For more information or tips please see 'Downloading to a citation manager' in the Help menu . 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