Electroredox carbene organocatalysis with iodide as promoter

Peng Zhou, Wenchang Li, Jianyong Lan and Tingshun Zhu ()
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Peng Zhou: Sun Yat-sen University
Wenchang Li: Sun Yat-sen University
Jianyong Lan: Sun Yat-sen University
Tingshun Zhu: Sun Yat-sen University

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: Abstract Oxidative carbene organocatalysis, inspired from Vitamin B1 catalyzed oxidative activation from pyruvate to acetyl coenzyme A, have been developed as a versatile synthetic method. To date, the α-, β-, γ-, δ- and carbonyl carbons of (unsaturated)aldehydes have been successfully activated via oxidative N-heterocyclic carbene (NHC) organocatalysis. In comparison with chemical redox or photoredox methods, electroredox methods, although widely used in mechanistic study, were much less developed in NHC catalyzed organic synthesis. Herein, an iodide promoted electroredox NHC organocatalysis system was developed. This system provided general solutions for electrochemical single-electron-transfer (SET) oxidation of Breslow intermediate towards versatile transformations. Radical clock experiment and cyclic voltammetry results suggested an anodic radical coupling pathway.

Date: 2022
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DOI: 10.1038/s41467-022-31453-7

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