Rhodium-catalyzed Z-alkenylation of gem-difluoropropenes: access to fluorinated (1Z,4Z)-dienes

Abstract

An effective method for constructing thermodynamically unstable 1Z,4Z-dienes via Rh-catalysed cross-coupling of allylic gem-difluorides with tertiary Z-allylic alcohols has been developed. The fluoride elimination of the gem-difluoride propenes and β-Z-alkenyl elimination of the tertiary Z-allylic alcohols have been combined smoothly. This transformation furnishes a series of fluorinated (1Z,4Z)-dienes in moderate-to-high yields under mild conditions, exhibiting broad substrate scope, excellent functional group tolerance, and excellent chemo- and regioselectivity.