A diastereoselective Pd-catalyzed allylic C–F bond functionalization of pentafluoroethyl alkenes is described. Heteroatom nucleophiles including amines, alcohols, and thiols can be employed to construct new C–N, C–O, or C–S bonds with concomitant cleavage of an allylic C–F bond. Both 1,1- and 1,2-disubstituted pentafluoroalkenes can be utilized to synthesize novel tetra- and trisubstituted alkenes containing an sp2-carbon connected to both F and CF3 in good to excellent diastereoselectivities.
Fu et al. (Mon,) studied this question.