A simple protocol for stereoselective construction of novel β-sulfanyl vinyl sulfonyl fluorides

The addition of thiols to 2-bromoprop-2-ene-1-sulfonyl fluoride (BPESF) in the presence of an organic base has been successfully employed for the synthesis of highly functionalized sulfanyl vinyl sulfonyl fluorides. This reaction features a broad substrate scope, mild reaction conditions, high atom economy, good to excellent isolated yields of up to 100%, and remarkable stereoselectivity, making it valuable for applications in chemical biology and medicinal chemistry. Further product diversification resulted in the construction of enaminyl sulfonyl fluorides.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc00029g
Citations
2
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
1.58

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article

A simple protocol for stereoselective construction of novel β-sulfanyl vinyl sulfonyl fluorides

Fayez Althobaiti, Hanadi A. Katouah, Eman Elsayed Fayad, Hua‐Li Qin et al.
2 citations
Chemical Communications
Fluorine in Organic Chemistry
1.58
article

A simple protocol for stereoselective construction of novel β-sulfanyl vinyl sulfonyl fluorides

Fayez Althobaiti, Hanadi A. Katouah, Eman Elsayed Fayad, Hua‐Li Qin, Monday Peter Ajisafe, Heba H. Mohamedy
article en
2 citations

Abstract

The addition of thiols to 2-bromoprop-2-ene-1-sulfonyl fluoride (BPESF) in the presence of an organic base has been successfully employed for the synthesis of highly functionalized sulfanyl vinyl sulfonyl fluorides. This reaction features a broad substrate scope, mild reaction conditions, high atom economy, good to excellent isolated yields of up to 100%, and remarkable stereoselectivity, making it valuable for applications in chemical biology and medicinal chemistry. Further product diversification resulted in the construction of enaminyl sulfonyl fluorides.

Chemical CommunicationsVol. 61(31)
Taif University (SA), Wuhan University of Technology (CN), Umm al-Qura University (SA)
Taif University
Openalex Percentile: Top 18%
Fluorine in Organic Chemistry
1.58
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