Hypervalent Iodine Mediated Synthesis of Sulfinamidines from Sulfenamides

In this study, we present a novel, efficient method for the oxidative amination of sulfenamides using diacetoxyiodobenzene (PhI­(OAc)2) and amines under basic conditions. This innovative technique streamlines the synthesis of sulfinamidines under mild, metal-free conditions, achieving outstanding yi...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-08, Vol.88 (16), p.11728-11734
Main Authors: Huang, Guoling, Ye, Jianlin, Bashir, Muhammad Adnan, Chen, Yuetong, Chen, Wenjing, Lu, Xunbo
Format: Article
Language:English
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Summary:In this study, we present a novel, efficient method for the oxidative amination of sulfenamides using diacetoxyiodobenzene (PhI­(OAc)2) and amines under basic conditions. This innovative technique streamlines the synthesis of sulfinamidines under mild, metal-free conditions, achieving outstanding yields of up to 99%. Furthermore, we propose possible pathways that elucidate the observed molecular sequence of events in this reaction. This cutting-edge approach not only advances the synthesis of valuable sulfinamidine compounds but also expands the synthetic toolbox available to chemists, paving the way for future discoveries in organic synthesis and potential applications in medicinal chemistry.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00999