Nickel-Catalyzed Cross-Electrophile Coupling Reactions between Allylic Acetates and -Difluorovinyl Tosylate.

Org Lett

West China School of Pharmacy and State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, Sichuan University, Chengdu, Sichuan 610041, People's Republic of China.

Published: May 2022

A nickel-catalyzed cross-electrophile coupling of allylic acetates and -difluorovinyl tosylate is presented, which first achieves allylic -difluoroolefins via C(sp)-C(sp) cross-electrophile coupling. In addition, this protocol was performed under mild reaction conditions, affording a variety of allylic -difluorovinyl arenes in moderate to good yields. Moreover, both linear and branched allylic acetate could produce a linear cross-coupling product exclusively. Mechanistic studies reveal that the reaction involves two different Ni(0)/Ni(II) catalytic cycles.

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http://dx.doi.org/10.1021/acs.orglett.2c01245DOI Listing

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