Cross-dehydrogenative coupling enables enantioselective access to CF(3)-substituted all-carbon quaternary stereocenters

A cross-dehydrogenative coupling strategy for enantioselective access to acyclic CF(3)-substituted all-carbon quaternary stereocenters has been established. By using catalytic DDQ with MnO(2) as an inexpensive terminal oxidant, asymmetric cross coupling of racemic δ-CF(3)-substituted phenols with indoles proceeded smoothly, providing CF(3)-bearing all-carbon quaternary stereocenters with excellent chemo- and enantioselectivities. The generality of the strategy is further demonstrated by efficient construction of all-carbon quaternary stereocenters bearing other polyfluoroalkyl and perfluoroalkyl groups such as CF(2)Cl, C(2)F(5), and C(3)F(7).