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- Title
Additions to N‐Sulfinylamines as an Approach for the Metal‐free Synthesis of Sulfonimidamides: O‐Benzotriazolyl Sulfonimidates as Activated Intermediates.
- Authors
Bremerich, Maximilian; Conrads, Christian M.; Langletz, Tim; Bolm, Carsten
- Abstract
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.
- Subjects
ARYL radicals; TERTIARY amines; TETRAFLUOROBORATES; DIAZONIUM compounds; CARBONATES
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 52, p19190
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201911075