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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...

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Autores principales: Laudadio, Gabriele, Bartolomeu, Aloisio de A., Verwijlen, Lucas M. H. M., Cao, Yiran, de Oliveira, Kleber T., Noël, Timothy
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
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.
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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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