e-Carbonyl: Electrochemical Synthesis of α-Keto Esters via α-Carbonyl Carbocations

Herein, we report a general and practical electrochemical method for the synthesis of α-keto esters from malonic acid derivatives via α-carbonyl carbocations. Although these cations are typically unstable, they can be efficiently generated under Hofer-Moest-type conditions when stabilized by an α-acetoxy substituent. This metal- and supporting-electrolyte-free approach grants straightforward access to α-keto esters that are otherwise challenging to obtain using conventional methods.

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Publication Details

Journal
Organic Letters
Published
2025-12-26
DOI
https://doi.org/10.1021/acs.orglett.5c04372
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

e-Carbonyl: Electrochemical Synthesis of α-Keto Esters via α-Carbonyl Carbocations

Hamid Salehzadeh, Charles A. I. Goodall, Antonio Del Vecchio, Marco Lessi et al.
Organic Letters
Radical Photochemical Reactions
article

e-Carbonyl: Electrochemical Synthesis of α-Keto Esters via α-Carbonyl Carbocations

Hamid Salehzadeh, Charles A. I. Goodall, Antonio Del Vecchio, Marco Lessi, Caterina Campinoti, Ewan V. Tushkanov, Kevin Lam
article en

Abstract

Herein, we report a general and practical electrochemical method for the synthesis of α-keto esters from malonic acid derivatives via α-carbonyl carbocations. Although these cations are typically unstable, they can be efficiently generated under Hofer-Moest-type conditions when stabilized by an α-acetoxy substituent. This metal- and supporting-electrolyte-free approach grants straightforward access to α-keto esters that are otherwise challenging to obtain using conventional methods.

Organic LettersVol. 28(1)
University of Pisa (IT), University of Greenwich (GB)
Openalex Percentile: Top 33%
Radical Photochemical Reactions
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