eCarbonyls: an electrochemical thioether mediated oxidation of alcohols to aldehydes and ketones

We report eCarbonyls, a scalable, metal-free electrochemical oxidation of alcohols that mimics key features of the classical Swern reaction while avoiding its reliance on cryogenic conditions and hazardous reagents. Operating at room temperature in an undivided cell, this process employs a stable thioether mediator to generate reactive radical cation intermediates that enable selective oxidation of primary and secondary alcohols to aldehydes and ketones. The method displays broad substrate scope, with up to 98% isolated yields across more than 25 examples, and excellent tolerance toward sensitive functional groups, including azides, boronates, and silyl ethers. Mechanistic studies confirm the role of anodically generated thioether radical cations and highlight the importance of the external base. Notably, eCarbonyls is readily scalable and adaptable to flow electrolysis, enabling multigram synthesis and offering a safe, sustainable platform for academic and industrial applications.

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Publication Details

Journal
Chemical Science
Published
2025-01-01
DOI
https://doi.org/10.1039/d5sc06546a
Primary Topic
Chemical Synthesis and Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

eCarbonyls: an electrochemical thioether mediated oxidation of alcohols to aldehydes and ketones

Katherine M. P. Wheelhouse, Kevin Lam, Cathryn Molloy, Lee J. Edwards et al.
Chemical Science
Chemical Synthesis and Reactions
article

eCarbonyls: an electrochemical thioether mediated oxidation of alcohols to aldehydes and ketones

Katherine M. P. Wheelhouse, Kevin Lam, Cathryn Molloy, Lee J. Edwards, Simon Kaltenberger
article en

Abstract

We report eCarbonyls, a scalable, metal-free electrochemical oxidation of alcohols that mimics key features of the classical Swern reaction while avoiding its reliance on cryogenic conditions and hazardous reagents. Operating at room temperature in an undivided cell, this process employs a stable thioether mediator to generate reactive radical cation intermediates that enable selective oxidation of primary and secondary alcohols to aldehydes and ketones. The method displays broad substrate scope, with up to 98% isolated yields across more than 25 examples, and excellent tolerance toward sensitive functional groups, including azides, boronates, and silyl ethers. Mechanistic studies confirm the role of anodically generated thioether radical cations and highlight the importance of the external base. Notably, eCarbonyls is readily scalable and adaptable to flow electrolysis, enabling multigram synthesis and offering a safe, sustainable platform for academic and industrial applications.

Chemical ScienceVol. 16(43)
University of Hertfordshire (GB), Christian-Albrechts-Universität zu Kiel (DE), University of Greenwich (GB)
Government of the United Kingdom, UK Research and Innovation, Christian-Albrechts-Universität zu Kiel, HORIZON EUROPE Framework Programme, HORIZON EUROPE European Innovation Council
Openalex Percentile: Top 78%
Chemical Synthesis and Reactions
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eCarbonyls: an electrochemical thioether mediated oxidation of alcohols to aldehydes and ketones — Katherine M. P. Wheelhouse, Kevin Lam, et al. · Chemical Science (2025) | TGRS Research Map | TGRS