Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents

[Image: see text] The direct α-sulfidation of tertiary amides using sulfoxide reagents under electrophilic amide activation conditions is described. Employing convenient and readily available reagents, selective functionalization takes place to generate isolable sulfonium ions en route to α-sulfide...

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Autores principales: Leypold, Mario, D’Angelo, Kyan A., Movassaghi, Mohammad
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7680396/
https://www.ncbi.nlm.nih.gov/pubmed/33048547
http://dx.doi.org/10.1021/acs.orglett.0c03160
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author Leypold, Mario
D’Angelo, Kyan A.
Movassaghi, Mohammad
author_facet Leypold, Mario
D’Angelo, Kyan A.
Movassaghi, Mohammad
author_sort Leypold, Mario
collection PubMed
description [Image: see text] The direct α-sulfidation of tertiary amides using sulfoxide reagents under electrophilic amide activation conditions is described. Employing convenient and readily available reagents, selective functionalization takes place to generate isolable sulfonium ions en route to α-sulfide amides. Mechanistic studies identified activated sulfoxides as promoters of the desired transformation and enabled the extension of the methodology from benzylic to aliphatic amide substrates.
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spelling pubmed-76803962020-11-25 Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents Leypold, Mario D’Angelo, Kyan A. Movassaghi, Mohammad Org Lett [Image: see text] The direct α-sulfidation of tertiary amides using sulfoxide reagents under electrophilic amide activation conditions is described. Employing convenient and readily available reagents, selective functionalization takes place to generate isolable sulfonium ions en route to α-sulfide amides. Mechanistic studies identified activated sulfoxides as promoters of the desired transformation and enabled the extension of the methodology from benzylic to aliphatic amide substrates. American Chemical Society 2020-10-13 2020-11-20 /pmc/articles/PMC7680396/ /pubmed/33048547 http://dx.doi.org/10.1021/acs.orglett.0c03160 Text en © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Leypold, Mario
D’Angelo, Kyan A.
Movassaghi, Mohammad
Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents
title Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents
title_full Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents
title_fullStr Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents
title_full_unstemmed Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents
title_short Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents
title_sort chemoselective α-sulfidation of amides using sulfoxide reagents
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7680396/
https://www.ncbi.nlm.nih.gov/pubmed/33048547
http://dx.doi.org/10.1021/acs.orglett.0c03160
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