Abstract
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 sp(2)-carbon connected to both F and CF(3) in good to excellent diastereoselectivities.