Copper-Catalyzed Regioselective Intramolecular Electrophilic Sulfenoamination via Lewis Acid Activation of Disulfides under Aerobic Conditions

Abstract

The activation of disulfides by Cu(II) salts has been realized, which triggers a highly efficient electrophilic sulfenoamination of alkenes under aerobic conditions. Various sulfenyl N-heterocycles and their Selena counterparts were produced regioselectively, with no competing disulfidation products detected. Mechanistic studies suggest a profound influence of the counterions on the Lewis acidic copper center, and the important roles of oxygen and DMSO as co-oxidants for these cyclization processes.