Rhodium-Catalyzed Z-Alkenylation of gem-Difluoropropenes for the Synthesis of Fluorinated (1Z,4Z)-Dienes

Abstract

A rhodium-catalyzed Z-alkenylation of gem-difluorpropenes has been developed. This is an effective method for constructing thermodynamically unstable 1Z,4Z-dienes via Rh-catalysed cross-coupling of allylic gem-difluorides with tertiary Z-allylic alcohols under mild conditions. In this procedure, the fluoride elimination of the gem-difluoride propenes and β-Z-alkenyl elimination of the tertiary Z-allylic alcohols have been combined smoothly, and provide the thermodynamically unstable fluoride skipped dienes with high chemoselectivity and stereoselectivity. This reaction exhibits a broad substrate scopes, moderate to high yields, good functional group tolerance, and excellent regioselectivity.