Electrochemical Three-Component Synthesis of Vinyl Sulfonamides via Decarboxylative Sulfonylation of Cinnamic Acids

An efficient, electrochemical three-component reaction for the synthesis of vinyl sulfonamides from cinnamic acids, SO₂, and amines is reported. This metal-free protocol utilizes inexpensive graphite electrodes and easy-to-use SO₂ stock solutions to facilitate a decarboxylative transformation under mild conditions. The reaction proceeds with high regio- and stereoselectivity, affording (E)-β-styryl sulfonamides without double-bond translocation. The use of cinnamic acid derivatives as biobased feedstocks, combined with the demonstrated scalability and anolyte reusability, highlights the potential of this approach for a sustainable synthesis of the important vinyl sulfonamide scaffold.

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Publication Details

Journal
ChemRxiv
Published
2025-08-21
DOI
https://doi.org/10.26434/chemrxiv-2025-gsqzx
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

Electrochemical Three-Component Synthesis of Vinyl Sulfonamides via Decarboxylative Sulfonylation of Cinnamic Acids

Harald Kelm, Po‐Chung Chien, Georg Manolikakes
ChemRxiv
Sulfur-Based Synthesis Techniques
article

Electrochemical Three-Component Synthesis of Vinyl Sulfonamides via Decarboxylative Sulfonylation of Cinnamic Acids

Harald Kelm, Po‐Chung Chien, Georg Manolikakes
article en

Abstract

An efficient, electrochemical three-component reaction for the synthesis of vinyl sulfonamides from cinnamic acids, SO₂, and amines is reported. This metal-free protocol utilizes inexpensive graphite electrodes and easy-to-use SO₂ stock solutions to facilitate a decarboxylative transformation under mild conditions. The reaction proceeds with high regio- and stereoselectivity, affording (E)-β-styryl sulfonamides without double-bond translocation. The use of cinnamic acid derivatives as biobased feedstocks, combined with the demonstrated scalability and anolyte reusability, highlights the potential of this approach for a sustainable synthesis of the important vinyl sulfonamide scaffold.

ChemRxiv
Openalex Percentile: Top 84%
Sulfur-Based Synthesis Techniques
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