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DOI: 10.1055/a-2360-9229
Thiourea/NCBSI/HCl System: Telescoping Alkyl Halide to Alkyl Sulfonyl Chloride by Recyclable N-Chloro-N-(phenylsulfonyl)benzene Sulfonamide (NCBSI)
Financial support was provided by Chhatrapati Shahu Maharaj Research, Training, and Human Development Institute, Govt. of Maharashtra, India (CSMNRF-2022/2022-23/2341).
Abstract
A convenient and efficient method to synthesize diverse alkyl sulfonyl chlorides through N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)-mediated oxidative chlorosulfonation of S-alkyl isothiouronium salts obtained from alkyl chlorides is presented. Synthesizing structurally diverse alkyl sulfonyl chloride in moderate to excellent yields up to 98% from alkyl halide was achieved via easy formation of S-alkyl isothiouronium salts using inexpensive thiourea. The mild reaction conditions and broad substrate scope make this method attractive for alkylsulfonyl chloride syntheses.
Key words
alkyl sulfonyl chlorides - N-chloro-N-(phenylsulfonyl)benzene sulfonamide - S-alkyl isothiouronium salts - alkyl halides - chlorosulfonationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2360-9229.
- Supporting Information
Publication History
Received: 27 September 2023
Accepted after revision: 05 July 2024
Accepted Manuscript online:
16 July 2024
Article published online:
26 August 2024
© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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