Oxidant-Triggered C1-Benzylation of Isoquinoline by Iodine-­Catalyzed Cross-Dehydrogenative-Coupling with Methylarenes

A practical iodine-catalyzed oxidative functionalization of isoquinolines with methylarenes is developed, which can be triggered by the selected oxidants to produce C 1 - or N -benzyl-substituted products selectively. This method utilizes readily available isoquinolines and methylarenes as starting materials and proceeds under metal-free conditions with broad substrate scope with respect to methylarenes, avoiding the usage of expensive metal catalysts and generation of halide and metal wastes.