期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 52, 页码 19014-19020出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201911075
关键词
diazonium salts; N-hydroxybenzotriazoles; N-tritylsulfinylamines; sulfonimidamides; sulfonimidates
Sulfonimidamides are obtained in moderate to very good yields from the key intermediates O-benzotriazolyl sulfonimidates, which are formed by reacting aryldiazonium tetrafluoroborates, N-tritylsulfinylamine, and N-hydroxybenzotriazole hydrate in a process mediated by a tertiary amine. The formation of the sulfonimidate proceeds in inexpensive and environmentally benign dimethyl carbonate as the solvent, it does not require anhydrous conditions, and the product yields generally exceed 70%. The substrate scope is broad, and a wide range of sensitive organic functionalities is well tolerated. The reactions probably proceed via aryl radicals formed from diazonium cations with assistance from both the tertiary amine and the sulfinylamine.
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