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Transfer of Electrophilic NH Using Convenient Sources of Ammonia. Direct Synthesis of N–H Sulfoximines from Sulfoxides

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Title: Transfer of Electrophilic NH Using Convenient Sources of Ammonia. Direct Synthesis of N–H Sulfoximines from Sulfoxides
Authors: Zenzola, M
Doran, R
Degennaro, L
Luisi, R
Bull, JA
Item Type: Journal Article
Abstract: © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.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+.
Issue Date: 29-Apr-2016
Date of Acceptance: 22-Mar-2016
URI: http://hdl.handle.net/10044/1/30457
DOI: https://dx.doi.org/10.1002/anie.201602320
ISSN: 1433-7851
Publisher: Wiley
Start Page: 7203
End Page: 7207
Journal / Book Title: Angewandte Chemie - International Edition
Volume: 55
Issue: 25
Sponsor/Funder: Engineering & Physical Science Research Council (EPSRC)
Engineering & Physical Science Research Council (E
The Royal Society
Funder's Grant Number: EP/J001538/1
EP/K503733/1
UF140161
Keywords: hypervalent compounds
nitrogen
reactive intermediates
sulfur
synthetic methods
Organic Chemistry
Chemical Sciences
Publication Status: Published
Appears in Collections:Chemistry
Faculty of Natural Sciences



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