Nickel-catalyzed cross-electrophile coupling of alkenyl sulfonium salts with alkyl bromides.

An efficient nickel-catalyzed C(sp2)-C(sp3) cross-electrophile coupling reaction between alkenyl sulfonium salts and alkyl bromides has been developed. This transformation proceeds smoothly through C-S bond functionalization under mild conditions, providing convenient access to diverse alkylated alkenes in modest to good yields. Notably, direct alkene alkylation can be achieved through a one-pot process without the isolation of alkenylsulfonium salts. The protocol features broad substrate scope, ease of scale-up, and applicability in the late-stage modification of complex molecules. Mechanistic studies suggested that the in situ-formed alkyl radical serves as the key intermediate in this cross-electrophile coupling process.