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Selective Construction of Xanthate-Functionalized Allylic Sulfonyl Fluorides via a Three-Component Process
Monday Peter Ajisafe1, Idrees Idrees Aliyu1, Bright Bassey Oyom2
1School of Materials Science and Engineering, Wuhan University of Technology, Wuhan 430070, China.
The Journal of Organic Chemistry
|February 3, 2026
Summary
A new one-pot method synthesizes novel xanthate-functionalized allylic sulfonyl fluorides using alcohols, carbon disulfide, and 2-chloroprop-2-ene-1-sulfonyl fluoride (CESF). This efficient process shows promise for medicinal chemistry applications.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
Background:
- Sulfonyl fluorides are versatile building blocks in organic synthesis.
- Sulfur (VI) fluoride exchange (SuFEx) click chemistry offers efficient molecular construction.
- Novel functionalized sulfonyl fluorides are needed for drug discovery.
Purpose of the Study:
- To develop a novel one-pot protocol for synthesizing xanthate-functionalized allylic sulfonyl fluorides.
- To explore the utility of these novel compounds in subsequent SuFEx reactions.
- To demonstrate the modification of natural and pharmaceutical compounds using the synthesized molecules.
Main Methods:
- A one-pot reaction involving alcohols, carbon disulfide, and 2-chloroprop-2-ene-1-sulfonyl fluoride (CESF).
- Purification and characterization of the synthesized xanthate-functionalized allylic sulfonyl fluorides.
- Subsequent Sulfur (VI) fluoride exchange (SuFEx) reactions and compound modifications.
Main Results:
- Selective synthesis of novel xanthate-functionalized allylic sulfonyl fluorides.
- High isolated yields achieved, up to 99%.
- Remarkable efficiency in subsequent SuFEx transformations and compound modifications.
Conclusions:
- The developed one-pot protocol provides efficient access to valuable xanthate-functionalized allylic sulfonyl fluorides.
- The synthesized compounds are highly effective in SuFEx click chemistry.
- This methodology holds significant potential for applications in biological and medicinal chemistry.
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