Bremerich Maximilian, Conrads Christian M, Langletz Tim, Bolm Carsten
Institut für Organische Chemie, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
Angew Chem Int Ed Engl. 2019 Dec 19;58(52):19014-19020. doi: 10.1002/anie.201911075. Epub 2019 Nov 11.
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.
磺酰亚胺酰胺可由关键中间体O-苯并三唑基磺酰亚胺酯以中等至非常好的产率获得，该中间体是通过在叔胺介导的过程中使芳基四氟硼酸重氮盐、N-三苯基亚磺酰基胺和N-羟基苯并三唑水合物反应形成的。磺酰亚胺酯的形成在廉价且环境友好的碳酸二甲酯作为溶剂中进行，不需要无水条件，并且产物产率通常超过70%。底物范围广泛，多种敏感的有机官能团都能很好地耐受。反应可能是通过重氮阳离子形成的芳基自由基在叔胺和亚磺酰基胺的共同协助下进行的。
