NCS-Mediated Direct Synthesis of β-Chlorosulfoxides from Unactivated Alkenes and Thiophenols

We report a streamlined one-pot methodology for the efficient synthesis of β-chlorosulfoxides from unactivated alkenes and aryl thiophenols using environmentally benign ethyl acetate as the reaction medium. The protocol utilizes N-chlorosuccinimide (NCS) in a dual capacity as both chlorine donor and intrinsic oxidant, thereby eliminating hazardous hydrochloric acid and external oxidizing agents. The scalability and reduced environmental impact position this strategy as a practical alternative to traditional multistep approaches.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-06-30
DOI
https://doi.org/10.1021/acs.joc.5c00884
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

NCS-Mediated Direct Synthesis of β-Chlorosulfoxides from Unactivated Alkenes and Thiophenols

Jin Zhang, Kai Huai Yang, Xin Huang, Gehua Bi et al.
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
article

NCS-Mediated Direct Synthesis of β-Chlorosulfoxides from Unactivated Alkenes and Thiophenols

Jin Zhang, Kai Huai Yang, Xin Huang, Gehua Bi, Zihan Cheng, Weimin Zhang, Siqiao Li, Mingyang Deng
article en

Abstract

We report a streamlined one-pot methodology for the efficient synthesis of β-chlorosulfoxides from unactivated alkenes and aryl thiophenols using environmentally benign ethyl acetate as the reaction medium. The protocol utilizes N-chlorosuccinimide (NCS) in a dual capacity as both chlorine donor and intrinsic oxidant, thereby eliminating hazardous hydrochloric acid and external oxidizing agents. The scalability and reduced environmental impact position this strategy as a practical alternative to traditional multistep approaches.

The Journal of Organic ChemistryVol. 90(27)
Shandong University of Technology (CN)
Openalex Percentile: Top 88%
Sulfur-Based Synthesis Techniques
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