An Approach to Aliphatic Sulfonyl Fluorides
Polina Dychkova1, Oleksandr P Datsenko1, Iryna Sadkova1
1Enamine Ltd., Chervonotkatska 78, 02094 Kyiv, Ukraine.
Organic Letters
|September 11, 2025
Summary
This study introduces a new method for C-H bond functionalization using decatungstate catalysts and vinyl sulfonyl fluoride. The process efficiently produces aliphatic sulfonyl fluorides from simple starting materials in scalable quantities.
Area of Science:
- Organic Chemistry
- Catalysis
- Flow Chemistry
Background:
- C-H bond functionalization is a key area in organic synthesis.
- Developing efficient and scalable methods for introducing functional groups is crucial.
- Vinyl sulfonyl fluoride is a versatile reagent for introducing sulfonyl fluoride moieties.
Purpose of the Study:
- To develop a photochemical method for C-H bond functionalization using vinyl sulfonyl fluoride.
- To utilize decatungstate catalysis in a flow chemistry setup.
- To achieve rapid and scalable synthesis of aliphatic sulfonyl fluorides.
Main Methods:
- Photochemical reactions catalyzed by decatungstate.
- Continuous flow processing for efficient reaction control and scalability.
- Utilizing vinyl sulfonyl fluoride as the functionalizing agent for C-H bonds.
Main Results:
- Rapid formation of aliphatic sulfonyl fluorides from various C-H substrates.
- Compatibility with simple and inexpensive starting materials like aldehydes, alcohols, and alkanes.
- Successful synthesis in milligram to multigram scales (up to 265 g).
Conclusions:
- Photochemical decatungstate catalysis in flow offers an efficient route to aliphatic sulfonyl fluorides.
- The method is versatile, scalable, and uses readily available C-H substrates.
- This approach provides a valuable tool for synthesizing sulfonyl fluoride compounds.
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