Electrochemical Dehydration of Sulfonic Acids to Their Anhydrides

We developed an electrochemical method for sulfonic anhydride synthesis and one-pot derivatization into sulfonamides and mesylates under mild conditions. Aliphatic sulfonic anhydrides were electrogenerated in up to a 74% yield. Since isolating these moisture-sensitive intermediates is challenging, the in situ-generated sulfonic anhydrides were directly converted into sulfonamides or alkyl sulfonates using amines or alcohols, respectively. This scalable process enables the synthesis of various nitrogen- and oxygen-based products in the multigram range.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-08-22
DOI
https://doi.org/10.1021/acs.joc.5c01155
Citations
2
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
1.87

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article

Electrochemical Dehydration of Sulfonic Acids to Their Anhydrides

Siegfried R. Waldvogel, Johannes Schneider, Enrico Lunghi, Annemijn M. van Koten
2 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
1.87
article

Electrochemical Dehydration of Sulfonic Acids to Their Anhydrides

Siegfried R. Waldvogel, Johannes Schneider, Enrico Lunghi, Annemijn M. van Koten
article en
2 citations

Abstract

We developed an electrochemical method for sulfonic anhydride synthesis and one-pot derivatization into sulfonamides and mesylates under mild conditions. Aliphatic sulfonic anhydrides were electrogenerated in up to a 74% yield. Since isolating these moisture-sensitive intermediates is challenging, the in situ-generated sulfonic anhydrides were directly converted into sulfonamides or alkyl sulfonates using amines or alcohols, respectively. This scalable process enables the synthesis of various nitrogen- and oxygen-based products in the multigram range.

The Journal of Organic ChemistryVol. 90(35)
Karlsruhe Institute of Technology (DE), Johannes Gutenberg University Mainz (DE), Max Planck Institute for Chemical Energy Conversion (DE)
Deutsche Forschungsgemeinschaft, Max-Planck-Gesellschaft
Clean water and sanitation
Openalex Percentile: Top 14%
Sulfur-Based Synthesis Techniques
1.87
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Electrochemical Dehydration of Sulfonic Acids to Their Anhydrides — Siegfried R. Waldvogel, Johannes Schneider, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS