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

被引:7
|
作者
Alam, Tipu [1 ]
Patel, Bhisma K. [1 ]
机构
[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, Assam, India
关键词
cross-coupling between two nucleophiles; metal and oxidant-free; Late-stage functionalizations; H-2 and N-2 as only by-product; radical mechanism; OXIDATION; ACIDS;
D O I
10.1002/chem.202303444
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
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页数:9
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