Synthesis 2013; 45(12): 1675-1682
DOI: 10.1055/s-0033-1338743
paper
© Georg Thieme Verlag Stuttgart · New York

Convenient and Environment-Friendly Synthesis of Sulfonyl Chlorides from S-Alkylisothiourea Salts via N-Chlorosuccinimide Chlorosulfonation

Zhanhui Yang
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Fax: +86(10)64435565   Email: jxxu@mail.buct.edu.cn
,
Jiaxi Xu*
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Fax: +86(10)64435565   Email: jxxu@mail.buct.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 19 March 2013

Accepted after revision: 17 April 2013

Publication Date:
15 May 2013 (online)


Abstract

A convenient, practical, and environmentally friendly method for the synthesis of sulfonyl chlorides has been developed. Structurally diverse sulfonyl chlorides were synthesized in moderate to excellent yields from S-alkylisothiourea salts, which can be easily prepared from readily accessible alkyl halides or mesylates and inexpensive thiourea, via N-chlorosuccinimide chlorosulfonation. In large-scale syntheses, the byproduct succinimide from ‘waste water’ can be conveniently converted into the starting reagent N-chlorosuccinimide with sodium hypochlorite (bleach) to make the method sustainable.

Supporting Information

 
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