Nickel-Catalyzed Stereoconvergent C(sp2)-F Alkenylation of Monofluoroalkenes

Abstract

The stereoconvergent synthesis of a single stereoisomer from E/Z-olefin mixtures remains one of the foremost challenges in organic synthesis. Herein, we describe a nickel-catalyzed stereoconvergent cross-coupling between E- and Z-mixed monofluoroalkenes and alkenyl electrophiles, which allows the construction of C(sp²)-C(sp²) bonds. This defluorinative transformation offers facile access to various 1,3-dienes with E-selectivity and good functional group tolerance. Preliminary mechanistic studies indicate that the reaction most likely proceeds through a migratory insertion/β-F elimination/isomerization process.