Issue 45, 2023
From the journal:

Chemical Science

An efficient and mild oxidative approach from thiols to sulfonyl derivatives with DMSO/HBr†

Hongye Wang,a   Zhaoting Li,a   Rongheng Dai,a   Ning Jiao ORCID logo a  and  Song Song ORCID logo *a  

* Corresponding authors

a State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd 38, Beijing 100191, China
E-mail: ssong@bjmu.edu.cn
Fax: +86-10-82805294

Abstract

A mild and practical method for synthesizing sulfonyl derivatives, which have a wide range of applications in pharmaceuticals, materials, and organic synthesis, was described through the oxidative functionalization of thiols with DMSO/HBr. The simple conditions, low cost and ready availability of DMSO/HBr, as well as the versatility of the transformations, make this strategy very powerful in synthesizing a variety of sulfonyl derivatives including sulfonamides, sulfonyl fluorides, sulfonyl azides, and sulfonates. Mechanistic studies revealed that DMSO served as the terminal oxidant, and HBr acted as both a nucleophile and a redox mediator to transfer the oxygen atom.

Graphical abstract: An efficient and mild oxidative approach from thiols to sulfonyl derivatives with DMSO/HBr

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Article information

DOI
https://doi.org/10.1039/D3SC04945K
Article type
Edge Article
Submitted
20 Sep 2023
Accepted
30 Oct 2023
First published
01 Nov 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 13228-13234

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An efficient and mild oxidative approach from thiols to sulfonyl derivatives with DMSO/HBr

H. Wang, Z. Li, R. Dai, N. Jiao and S. Song, Chem. Sci., 2023, 14, 13228 DOI: 10.1039/D3SC04945K

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