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Synergistic silver-mediated and palladium-catalyzed nondirected olefination of aryl C–H bond: quick access to multi-substituted aryl olefins

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Science China Chemistry 2024年第3期67卷 882-889页

作者： Jian Yao Lili Shao Xiaohong Huo Xiaoming Wang Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs Frontiers Science Center for Transformative MoleculesSchool of Chemistry and Chemical EngineeringShanghai Jiao Tong UniversityShanghai 200240China State Key Laboratory of Organometallic Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 20032China School of Chemistry and Materials Science Hangzhou Institute for Advanced StudyUniversity of Chinese Academy of SciencesHangzhou 310024China

Transition metal-catalyzed olefination of aryl C-H bond is a powerful tool for the synthesis of alkenes. While the Pd-catalyzed oxidative C-H olefination of arenes, also known as Fujiwara-Moritani reaction, has been established as one of the most efficient methods, the substrates are largely limited to terminal olefins with electron-withdrawing group(s). Herein, we report a synergistic silver-mediated and palladium-catalyzed non-directed C-H olefination of arenes with vinyl(pseudo)halides, which offers a complementary strategy to the typical Fujiwara-Moritani reaction. The reactions proceeded well for a variety of halogenated arenes, heteroarenes, and olefin substrates, providing an efficient access to various multi-substituted aryl olefins, including trisubstituted/tetrasubstituted olefins and several complex olefins derived from medicines or natural products. Mechanistic studies indicated a bimetallic Pd/Ag cooperation is operative in the catalysis, i.e., the reaction is initiated by aryl C-H bond cleavage via ligation with phosphine/Ag species, followed by transferring of the aryl moiety to a vinyl palladium intermediate,which is in turn formed by oxidative addition of vinyl(pseudo)halide to a Pd complex. This method enables the synthesis of a wide range of challenging multi-substituted vinyl products from simple arenes(directing-group free) in a streamlined and controllable fashion.

关键词： direct C–H olefination multi-substituted aryl alkenes bimetallic Pd/Ag cooperation C–H functionalization

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