Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 25, Pages 7203-7207Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201602320
Keywords
hypervalent compounds; nitrogen; reactive intermediates; sulfur; synthetic methods
Categories
Funding
- EPSRC [CAF] [EP/J001538/1]
- EPSRC [Impact Acceleration Account] [EP/K503733/1]
- Royal Society
- Imperial College London
- Regione Puglia: Reti di Laboratori pubblici di ricerca Project [20]
- Project Laboratorio Sistema - MIUR [PONa300369]
- University of Bari
- Engineering and Physical Sciences Research Council [EP/K503733/1, EP/J001538/1] Funding Source: researchfish
- EPSRC [EP/J001538/1] Funding Source: UKRI
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A new system for NH transfer is developed for the preparation of sulfoximines, which are emerging as valuable motifs for drug discovery. The protocol employs readily available sources of nitrogen without the requirement for either preactivation or for metal catalysts. Mixing ammonium salts with diacetoxyiodobenzene directly converts sulfoxides into sulfoximines. This report describes the first example of using of ammonia sources with diacetoxyiodobenzene to generate an electrophilic nitrogen center. Control and mechanistic studies suggest a short-lived electrophilic intermediate, which is likely to be PhINH or PhIN+.
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