Synthesis of gem-Difluoroalkenes by Merging Ni-Catalyzed C-F and C-C Bond Activation in Cross-Electrophile Coupling.

Abstract

By merging C-F and C-C bond activation in the cross-electrophile coupling, we developed an efficient cyanide-free synthesis of diverse functional-group-rich cyano-substituted gem-difluoroalkenes using cyclobutanone oxime esters and trifluoromethyl alkenes as precursors. Notably, this Ni-catalyzed reaction is bestowed with broad substrate scope, low catalyst loading, complete regioselectivities, and high tolerance of a wide range of sensitive functional groups. Preliminary mechanistic studies indicate that an iminyl radical-initiated C-C bond cleavage is involved in the reaction pathway.