Synthesis of gem-Difluoroalkenes by Copper-catalyzed Regioselective Hydrodefluorination of 1-Trifluoromethylalkenes

A copper-catalyzed regioselective hydrodefluorination of 1-trifluoromethylalkenes with hydrosilanes has been developed. The copper catalysis is compatible with several functional groups, including alkyl chloride, ether, ester, nitrile, and imide moieties, to form the corresponding gem-difluoroalkenes in good yields. Additionally, asymmetric induction is also possible by using the chiral DTBM-SEGPHOS ligand, and gem-difluoroalkene with point chirality at the allylic position is obtained with high enantioselectivity. A copper-catalyzed regioselective hydrodefluorination of 1-trifluoromethylalkenes with hydrosilanes has been developed. The copper catalysis is compatible with several functional groups to form the corresponding gem-difluoroalkenes in good yields. Additionally, the asymmetric induction is also possible by using the chiral DTBM-SEGPHOS ligand, and the gem-difluoroalkene with the point chirality at the allylic position is obtained with high enantioselectivity.