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Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride
[Image: see text] Sulfonyl fluorides are valuable synthetic motifs for a variety of applications, among which sulfur(VI) fluoride exchange-based “click chemistry” is currently the most prominent. Consequently, the development of novel and efficient synthetic methods to access these functional groups...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2019
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6676414/ https://www.ncbi.nlm.nih.gov/pubmed/31303004 http://dx.doi.org/10.1021/jacs.9b06126 |
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author | Laudadio, Gabriele Bartolomeu, Aloisio de A. Verwijlen, Lucas M. H. M. Cao, Yiran de Oliveira, Kleber T. Noël, Timothy |
author_facet | Laudadio, Gabriele Bartolomeu, Aloisio de A. Verwijlen, Lucas M. H. M. Cao, Yiran de Oliveira, Kleber T. Noël, Timothy |
author_sort | Laudadio, Gabriele |
collection | PubMed |
description | [Image: see text] Sulfonyl fluorides are valuable synthetic motifs for a variety of applications, among which sulfur(VI) fluoride exchange-based “click chemistry” is currently the most prominent. Consequently, the development of novel and efficient synthetic methods to access these functional groups is of great interest. Herein, we report a mild and environmentally benign electrochemical approach to prepare sulfonyl fluorides using thiols or disulfides, as widely available starting materials, in combination with KF, as an inexpensive, abundant and safe fluoride source. No additional oxidants nor additional catalysts are required and, due to mild reaction conditions, the reaction displays a broad substrate scope, including a variety of alkyl, benzyl, aryl and heteroaryl thiols or disulfides. |
format | Online Article Text |
id | pubmed-6676414 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-66764142019-08-07 Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride Laudadio, Gabriele Bartolomeu, Aloisio de A. Verwijlen, Lucas M. H. M. Cao, Yiran de Oliveira, Kleber T. Noël, Timothy J Am Chem Soc [Image: see text] Sulfonyl fluorides are valuable synthetic motifs for a variety of applications, among which sulfur(VI) fluoride exchange-based “click chemistry” is currently the most prominent. Consequently, the development of novel and efficient synthetic methods to access these functional groups is of great interest. Herein, we report a mild and environmentally benign electrochemical approach to prepare sulfonyl fluorides using thiols or disulfides, as widely available starting materials, in combination with KF, as an inexpensive, abundant and safe fluoride source. No additional oxidants nor additional catalysts are required and, due to mild reaction conditions, the reaction displays a broad substrate scope, including a variety of alkyl, benzyl, aryl and heteroaryl thiols or disulfides. American Chemical Society 2019-07-13 2019-07-31 /pmc/articles/PMC6676414/ /pubmed/31303004 http://dx.doi.org/10.1021/jacs.9b06126 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes. |
spellingShingle | Laudadio, Gabriele Bartolomeu, Aloisio de A. Verwijlen, Lucas M. H. M. Cao, Yiran de Oliveira, Kleber T. Noël, Timothy Sulfonyl Fluoride Synthesis through Electrochemical Oxidative Coupling of Thiols and Potassium Fluoride |
title | Sulfonyl
Fluoride Synthesis through Electrochemical
Oxidative Coupling of Thiols and Potassium Fluoride |
title_full | Sulfonyl
Fluoride Synthesis through Electrochemical
Oxidative Coupling of Thiols and Potassium Fluoride |
title_fullStr | Sulfonyl
Fluoride Synthesis through Electrochemical
Oxidative Coupling of Thiols and Potassium Fluoride |
title_full_unstemmed | Sulfonyl
Fluoride Synthesis through Electrochemical
Oxidative Coupling of Thiols and Potassium Fluoride |
title_short | Sulfonyl
Fluoride Synthesis through Electrochemical
Oxidative Coupling of Thiols and Potassium Fluoride |
title_sort | sulfonyl
fluoride synthesis through electrochemical
oxidative coupling of thiols and potassium fluoride |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6676414/ https://www.ncbi.nlm.nih.gov/pubmed/31303004 http://dx.doi.org/10.1021/jacs.9b06126 |
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