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

• DOI: 10.1021/acs.orglett.2c01245
• Publication Date: 2022-05-05T16:07:00Z
• Authors: Xiaochun He; Jiangjun Liu; Gang Chen; Baojian Xiong; Xue Xiao; Lei Chen; Xuemei Zhang; Lin Dong; Xuelei Ma; Zhong Lian
• Keywords: Nickel; Acetates; 01 natural sciences; Catalysis; 0104 chemical sciences

A nickel-catalyzed cross-electrophile coupling of allylic acetates and gem-difluorovinyl tosylate is presented, which first achieves allylic gem-difluoroolefins via C(sp3)-C(sp2) cross-electrophile coupling. In addition, this protocol was performed under mild reaction conditions, affording a variety of allylic gem-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.