Photoredox-Catalyzed Aminosulfonylation of <i>gem</i> -Difluoroalkenes via the Ritter Reaction

A photocatalytic aminosulfonylation reaction of <i>gem</i>-difluoroalkenes, sulfonyl chlorides, and nitriles was successfully developed through a three-component Ritter-type reaction, with nitriles serving as both reactants and solvents. This efficient difunctionalization protocol is allowed for the synthesis of α,α-difluoromethyl-β-amidesulfonyl compounds in one step under mild conditions. The reaction exhibited broad functional group compatibility and particularly good reactivity with various nitriles. These products can be used as platform molecules for further modification. A possible mechanism was also proposed based on mechanistic experiments.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-11-24
DOI
https://doi.org/10.1021/acs.joc.5c02494
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Photoredox-Catalyzed Aminosulfonylation of gem -Difluoroalkenes via the Ritter Reaction

S. İsmat Shah, Ahmad Raheel, Jinkui Chai, Junliang Wu et al.
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
article

Photoredox-Catalyzed Aminosulfonylation of gem -Difluoroalkenes via the Ritter Reaction

S. İsmat Shah, Ahmad Raheel, Jinkui Chai, Junliang Wu, Fengqian Zhao, Lijuan Han
article en

Abstract

A photocatalytic aminosulfonylation reaction of <i>gem</i>-difluoroalkenes, sulfonyl chlorides, and nitriles was successfully developed through a three-component Ritter-type reaction, with nitriles serving as both reactants and solvents. This efficient difunctionalization protocol is allowed for the synthesis of α,α-difluoromethyl-β-amidesulfonyl compounds in one step under mild conditions. The reaction exhibited broad functional group compatibility and particularly good reactivity with various nitriles. These products can be used as platform molecules for further modification. A possible mechanism was also proposed based on mechanistic experiments.

The Journal of Organic ChemistryVol. 90(48)
Henan University of Technology (CN), Zhengzhou University (CN), Henan Institute of Technology (CN)
Openalex Percentile: Top 71%
Fluorine in Organic Chemistry
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