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.
Authors
- Harald Kelm (ORCID: https://orcid.org/0000-0001-9264-9437)
- Po‐Chung Chien (ORCID: https://orcid.org/0009-0003-2379-910X)
- Georg Manolikakes (ORCID: https://orcid.org/0000-0002-4013-5757)
- Siegfried R. Waldvogel (ORCID: https://orcid.org/0000-0002-7949-9638)
- Florian A. Breitschaft
Institutions
- University of Kaiserslautern (DE)
- Max Planck Institute for Chemical Energy Conversion (DE)
- Rheinland-Pfälzische Technische Universität Kaiserslautern-Landau (DE)
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