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Alkoxysulfonyl radical species: acquisition and transformation towards sulfonate esters through electrochemistry

Sulfonyl radical mediated processes have been considered as a powerful strategy for the construction of sulfonyl compounds. However, an efficient and high atom-economical radical approach to the synthesis of sulfonate esters is still rare, owing to the limited tactics to achieve alkoxysulfonyl radic...

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Autores principales: Zhang, Chun, Yang, Man, Qiu, Yanjie, Song, Meijun, Wang, Hongyan, Yang, Min, Xie, Wenlin, Wu, Jie, Ye, Shengqing
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9580505/
https://www.ncbi.nlm.nih.gov/pubmed/36320920
http://dx.doi.org/10.1039/d2sc04027a
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author Zhang, Chun
Yang, Man
Qiu, Yanjie
Song, Meijun
Wang, Hongyan
Yang, Min
Xie, Wenlin
Wu, Jie
Ye, Shengqing
author_facet Zhang, Chun
Yang, Man
Qiu, Yanjie
Song, Meijun
Wang, Hongyan
Yang, Min
Xie, Wenlin
Wu, Jie
Ye, Shengqing
author_sort Zhang, Chun
collection PubMed
description Sulfonyl radical mediated processes have been considered as a powerful strategy for the construction of sulfonyl compounds. However, an efficient and high atom-economical radical approach to the synthesis of sulfonate esters is still rare, owing to the limited tactics to achieve alkoxysulfonyl radicals. Herein, an electrochemical anodic oxidation of inorganic sulfites with alcohols is developed to afford alkoxysulfonyl radical species, which are utilized in subsequent alkene difunctionalization to provide various sulfonate esters. This transformation features excellent chemoselectivity and broad functional group tolerance. This new discovery presents the potential prospect for the construction of sulfonate esters, and enriches the electrochemical reaction type.
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spelling pubmed-95805052022-10-31 Alkoxysulfonyl radical species: acquisition and transformation towards sulfonate esters through electrochemistry Zhang, Chun Yang, Man Qiu, Yanjie Song, Meijun Wang, Hongyan Yang, Min Xie, Wenlin Wu, Jie Ye, Shengqing Chem Sci Chemistry Sulfonyl radical mediated processes have been considered as a powerful strategy for the construction of sulfonyl compounds. However, an efficient and high atom-economical radical approach to the synthesis of sulfonate esters is still rare, owing to the limited tactics to achieve alkoxysulfonyl radicals. Herein, an electrochemical anodic oxidation of inorganic sulfites with alcohols is developed to afford alkoxysulfonyl radical species, which are utilized in subsequent alkene difunctionalization to provide various sulfonate esters. This transformation features excellent chemoselectivity and broad functional group tolerance. This new discovery presents the potential prospect for the construction of sulfonate esters, and enriches the electrochemical reaction type. The Royal Society of Chemistry 2022-09-30 /pmc/articles/PMC9580505/ /pubmed/36320920 http://dx.doi.org/10.1039/d2sc04027a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Zhang, Chun
Yang, Man
Qiu, Yanjie
Song, Meijun
Wang, Hongyan
Yang, Min
Xie, Wenlin
Wu, Jie
Ye, Shengqing
Alkoxysulfonyl radical species: acquisition and transformation towards sulfonate esters through electrochemistry
title Alkoxysulfonyl radical species: acquisition and transformation towards sulfonate esters through electrochemistry
title_full Alkoxysulfonyl radical species: acquisition and transformation towards sulfonate esters through electrochemistry
title_fullStr Alkoxysulfonyl radical species: acquisition and transformation towards sulfonate esters through electrochemistry
title_full_unstemmed Alkoxysulfonyl radical species: acquisition and transformation towards sulfonate esters through electrochemistry
title_short Alkoxysulfonyl radical species: acquisition and transformation towards sulfonate esters through electrochemistry
title_sort alkoxysulfonyl radical species: acquisition and transformation towards sulfonate esters through electrochemistry
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9580505/
https://www.ncbi.nlm.nih.gov/pubmed/36320920
http://dx.doi.org/10.1039/d2sc04027a
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