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

A highly diastereoselectivePd(0)-catalyzed Mizoroki-Heckreaction of gem-difluoroalkenes is described. Unlikepreviously reported C-F bond functionalization with organometallicreagents, this reaction takes place between two different alkenesto achieve a formal C-F and C-H bond cross-couplingvia a distinct pathway. Monofluorinated 1,3-diene products can besynthesized with control of the geometry of each alkene and good functionalgroup tolerability.

Automated summary

A highly diastereoselective Pd(0)-catalyzed Mizoroki-Heck reaction of gem-difluoroalkenes is reported. This reaction allows for cross-coupling of a C-F and C-H bond by reacting two different alkenes through a distinct pathway. Mono-fluorinated 1,3-diene products can be synthesized with control over each alkene's geometry and good functional group tolerance.