Electrochemical N-Aroylation of Sulfoximines by Using Benzoyl Hydrazines with H2 Generation

Developed here is a robust electrochemical cross-coupling reaction between aroyl hydrazine and NH-sulfoximine via concomitant cleavage and formation of C(sp(2))-N bonds with the evolution of H-2 and N-2 as innocuous by-products. This sustainable protocol avoids the use of toxic reagents and occurs at room temperature. The reaction proceeds via the generation of an aroyl and a sulfoximidoyl radical via anodic oxidation under constant current electrolysis (CCE), affording N-aroylated sulfoximine. The strategy is applied to late-stage sulfoximidation of L-menthol, (-)-borneol, D-glucose, vitamin-E derivatives, and marketed drugs such as probenecid, ibuprofen, flurbiprofen, ciprofibrate, and sulindac. In addition, the present methodology is mild, high functional group tolerance with broad substrate scope and scalable.