A General Procedure for the Regioselective Synthesis of Aryl Thioethers and Aryl Selenides Through C-H Activation of Arenes

A general procedure for the synthesis of aryl thioethers and aryl selenides in one-pot through sequential iridium-catalyzed C-H borylation and copper-promoted C-S and C-Se bond formation is described. Functional groups including chloro, nitro, fluoro, trifluoromethyl, and nitrogen-containing heterocycles were all tolerated under the reaction conditions. Importantly, not only aryl thiols and selenides but also their alkyl analogs were suitable coupling partners, and the products were obtained in good yields with high meta regioselectivity.