Stereoselective Palladium-Catalyzed C-F Bond Alkenylation of Tetrasubstituted gem-Difluoroalkenes via Mizoroki-Heck Reaction.

ABSTRACT

A highly diastereoselective Pd(0)-catalyzed Mizoroki-Heck reaction of gem-difluoroalkenes is described. Unlike previously reported C-F bond functionalization with organometallic reagents, this reaction takes place between two different alkenes to achieve a formal C-F and C-H bond cross-coupling via a distinct pathway. Monofluorinated 1,3-diene products can be synthesized with control of the geometry of each alkene and good functional group tolerability.