Synthesis
DOI: 10.1055/s-0043-1775384
paper
SuFEx Chemistry

A Convenient One-Pot Process for Converting Thiols into Sulfonyl Fluorides Using H2O2 as an Oxidant

Guang Tao
a   School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, Wuhan 430070, P. R. of China
,
Eman Fayad
b   Department of Biotechnology, College of Sciences, Taif University, P.O. Box 11099, Taif 21944, Saudi Arabia
,
Ola A. Abu Ali
c   Department of Chemistry, College of Science, Taif University, Taif 21944, Saudi Arabia
,
Bright Oyom
a   School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, Wuhan 430070, P. R. of China
,
Hua-Li Qin
a   School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, Wuhan 430070, P. R. of China
› Author Affiliations
We are grateful to the National Natural Science Foundation of China (Grant No. 22071190) and Wuhan University of Technology for financial support. The authors also extend our appreciation to Taif University, Saudi Arabia, for supporting this work through project number (TU-DSPP-2024-85).


Abstract

A novel protocol for synthesizing sulfonyl fluorides from thiols in one pot is reported. Utilizing SOCl2 and H2O2 as low-cost and convenient reagents allows the direct oxidative chlorination of readily available thiol derivatives to give the corresponding sulfonyl chlorides, with subsequent fluoride–chloride exchange mediated by KHF2 giving access to the desired sulfonyl fluorides. This transformation features mild conditions, operational simplicity and high efficiency, and utilizes a broad substrate scope, including a variety of aryl, alkyl, benzyl and heteroaryl thiols.

Supporting Information



Publication History

Received: 24 April 2024

Accepted after revision: 25 June 2024

Article published online:
19 July 2024

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