Regioselective C–F Bond Transformations of Silyl Difluoroenolates

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Herein, we report the development of a nickel-catalyzed cross-coupling reaction of silyl difluoroenolates with aryl zinc reagents via C–F bond cleavage. Treatment of a stoichiometric amount of Ni(0)/ N -heterocyclic carbene (NHC) with silyl difluoroenolates in the presence of a lithium salt resulted in C–F bond cleavage to selectively afford the corresponding ( Z )-alkenyl Ni complexes. On the basis of the observations, we developed a catalytic cross-coupling reaction that selectively delivers a single geometric isomer of a fluoroenolate.