Access to Vinyl Gem-Difluorinated Cyclopropanes Via Photopromoted Palladium-Catalyzed Heck Reaction

Abstract

A photopromoted Pd-catalyzed Heck reaction of gem-difluorocyclopropyl bromides (DFCBs) with styrenes to deliver vinyl gem-difluorinated cyclopropanes (VDFCs) under mild conditions has been developed. The reaction demonstrates good functional group compatibility while providing high E/Z ratio of the products. Furthermore, the desired VDFCs can be easily transformed into fluorinated cyclic/acyclic architectures, which may broaden its applications in organic synthesis.

Keywords: Heck reaction; Palladium catalysis; Photocatalysis; Vinyl gem-difluorinated cyclopropanes.