Synthesis of sulfoximines and sulfonimidamides using hypervalent iodine mediated NH transfer
File(s)molecules-28-01120-v2.pdf (4.19 MB)
Published version
Author(s)
Luisi, Renzo
Bull, James
Type
Journal Article
Abstract
The development of NH transfer reactions using hypervalent iodine and simple sources of ammonia has facilitated the synthesis of sulfoximines and sulfonimidamides for applications across the chemical sciences. Perhaps most notably, the methods have been widely applied in medicinal chemistry and in the preparation of biologically active compounds, including in the large-scale preparation of an API intermediate. This review provides an overview of the development of these synthetic methods involving an intermediate iodonitrene, since our initial report in 2016 on the conversion of sulfoxides to sulfoximines. This review covers the NH transfer to sulfoxides and sulfinamides, and the simultaneous NH/O transfer to sulfides and sulfenamides to form sul-foximines and sulfonimidamides respectively. The mechanism of the reactions and identification of key intermediates are discussed. Developments in the choice of reagents and in the reaction conditions and set-ups used are described.
Date Issued
2023-01-22
Date Acceptance
2023-01-12
Citation
Molecules, 2023, 28 (3), pp.1-15
ISSN
1420-3049
Publisher
MDPI AG
Start Page
1
End Page
15
Journal / Book Title
Molecules
Volume
28
Issue
3
Copyright Statement
© 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
License URL
Identifier
https://doi.org/10.3390/molecules28031120
Publication Status
Published
Article Number
1120
Date Publish Online
2023-01-22