Regioselective Alkylpolyfluoroarylation of Styrenes by Copper-Catalyzed C(sp 3 )-H and C(sp 2 )-H Double Activation.

A novel dehydrogenative dicarbofunctionalization of vinyl arenes with polyfluoroarenes and unactivated alkanes enabled by copper catalysis has been accomplished under mild conditions. This transformation provides a regioselective route to highly functionalized polyfluoroaryl compounds that occur as structural scaffolds in a variety of pharmaceuticals and materials. Preliminary mechanistic studies indicate that the carbon-based radical and copper intermediate are involved in the reaction, and the reaction pathway is dominated by the bond dissociation energy (BDE) of C(sp 3 )-H bonds.