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

Abstract

Developed here is a robust electrochemical cross‐coupling reaction between aroyl hydrazine and NH‐sulfoximine via concomitant cleavage and formation of C(sp2)−N bonds with the evolution of H2 and N2 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.

PIDA/I2-mediated photo-induced aerobic N-acylation of sulfoximines with methylarenes

“…Our group is actively involved in exploring sulfoximine chemistry and developed thermal, photochemical, and electrochemical strategies for sulfoximine functionalization. 10 As a part of the ongoing research, we envisioned designing a strategy between methylarenes and NH-sulfoximines under the influence of visible light. To synchronize this assumption, a reaction was carried out between S -phenyl- S -methylsulfoximine ( a , 1 equiv.…”

Electrochemical N(sp2)–H/C(sp3)–H cross-coupling reaction between sulfoximines and alkylarenes

“…Particularly, the advantages, such as using trace electricity to realize the oxidation and reduction, bearing the characteristics of external oxidants and reductants free, mild reaction conditions and low waste emission, make electrochemical synthesis more attractive. 11 In fact, the electrochemical method has been employed for the N–H functionalization reactions of sulfoximines, including arylation reactions, 12 acylation reactuons, 13 three-component alkylation reaction, 14 sulfenylation and phosphinylation. 15 Among them, however, we find that there is only one example of the hetero-CDC reaction of sulfoximines with C(sp 3 )–H bonds.…”