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

The stereoconvergent synthesis of a single stereoisomer from <i>E</i>/<i>Z</i>-olefin mixtures remains one of the foremost challenges in organic synthesis. Herein, we describe a nickel-catalyzed stereoconvergent cross-coupling between <i>E</i>- and <i>Z</i>-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 <i>E</i>-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.