Synthesis of <i>gem</i>-Difluoroalkenes via Nickel-Catalyzed Allylic Defluorinative Reductive Cross-Coupling

Abstract

In this protocol, we report an allylic defluorinative reductive cross-coupling reaction for C–C bond formation. Under the Ni-catalysis the challenging C(sp3)–F bond cleavage of trifluoromethyl-substituted alkenes was achieved with easily accessible primary, secondary and tertiary alkyl halides as the coupling partners and Zn-powder as reducing agent. This process provides an efficient and convenient entry to gem-difluoroalkenes bearing various sensitive functional groups under mild reaction conditions. Moreover, this method proves to be suitable for late-stage functionalization of multifunctional complex molecules.