Additions to N-Sulfinylamines as an Approach for the Metal-free Synthesis of Sulfonimidamides: O-Benzotriazolyl Sulfonimidates as Activated Intermediates
Additions to N-Sulfinylamines as an Approach for the Metal-free Synthesis of Sulfonimidamides: O-Benzotriazolyl Sulfonimidates as Activated Intermediates
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DOI：
10.1002/anie.201911075
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发表时间：
2019-11-11
影响因子：
16.6
通讯作者：
Bolm, Carsten
中科院分区：
文献类型：
--
作者：
Bremerich, Maximilian;Conrads, Christian M.;Bolm, Carsten
主要中间体o -苯并三唑基磺酰酰咪甲酸酯是由芳基重氮四氟硼酸盐、n -三烷基亚胺和n -羟基苯并三唑水合物在叔胺介导的反应过程中生成的。磺胺咪酯的生成以廉价、环保的碳酸二甲酯为溶剂，不需要无水条件，产品收率一般超过70%。底物范围广，对各种敏感的有机功能具有良好的耐受性。该反应可能通过重氮离子在叔胺和亚砜胺的辅助下形成的芳基自由基进行。
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.