Electrochemical Three‐component Synthesis of Alkenesulfonates from Cinnamic Acids, SO <sub>2</sub> , and Alcohols

A novel, electrochemical three-component reaction for the synthesis of alkyl alkenesulfonates from cinnamic acids, SO<sub>2</sub>, and alkyl alcohols is reported. This metal-free process employs inexpensive and readily available graphite electrodes in combination with easy-to-use stock solutions of SO<sub>2</sub> and enables a straightforward construction of the styrene sulfonate scaffold via a decarboxylative transformation. Mechanistic studies indicate a pseudo-Kolbe type reaction. This novel reaction pathway enables a regioselective synthesis of alkenesulfonates from substituted cinnamic acids without double-bond translocation. Gram-scale and anolyte reusability experiments demonstrate the applicability of this process for the construction of alkenesulfonates from cinnamic acids as potential biogenic feedstock.

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Publication Details

Journal
ChemSusChem
Published
2025-03-11
DOI
https://doi.org/10.1002/cssc.202500186
Citations
3
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
2.81
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article

Electrochemical Three‐component Synthesis of Alkenesulfonates from Cinnamic Acids, SO 2 , and Alcohols

Harald Kelm, Po‐Chung Chien, Georg Manolikakes, Siegfried R. Waldvogel et al.
3 citations
ChemSusChem
Sulfur-Based Synthesis Techniques
2.81
article

Electrochemical Three‐component Synthesis of Alkenesulfonates from Cinnamic Acids, SO 2 , and Alcohols

Harald Kelm, Po‐Chung Chien, Georg Manolikakes, Siegfried R. Waldvogel, Florian A. Breitschaft
article en
3 citations

Abstract

A novel, electrochemical three-component reaction for the synthesis of alkyl alkenesulfonates from cinnamic acids, SO<sub>2</sub>, and alkyl alcohols is reported. This metal-free process employs inexpensive and readily available graphite electrodes in combination with easy-to-use stock solutions of SO<sub>2</sub> and enables a straightforward construction of the styrene sulfonate scaffold via a decarboxylative transformation. Mechanistic studies indicate a pseudo-Kolbe type reaction. This novel reaction pathway enables a regioselective synthesis of alkenesulfonates from substituted cinnamic acids without double-bond translocation. Gram-scale and anolyte reusability experiments demonstrate the applicability of this process for the construction of alkenesulfonates from cinnamic acids as potential biogenic feedstock.

ChemSusChemVol. 18(12)
University of Kaiserslautern (DE), Max Planck Institute for Chemical Energy Conversion (DE), Rheinland-Pfälzische Technische Universität Kaiserslautern-Landau (DE)
Clean water and sanitation
Openalex Percentile: Top 12%
Sulfur-Based Synthesis Techniques
2.81
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