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Organocatalyzed Anodic Oxidation of Aldehydes

Author:
Finney, Eric E., Ogawa, Kelli A., Boydston, Andrew J.
Source:
Journal of the American Chemical Society 2012 v.134 no.30 pp. 12374-12377
ISSN:
1520-5126
Subject:
alcohols, aldehydes, esters, hydrogen, oxidation
Abstract:
A method for the catalytic formation of electroauxiliaries and subsequent anodic oxidation has been developed. The process interfaces N-heterocyclic carbene-based organocatalysis with electro-organic synthesis to achieve direct oxidation of catalytically generated electroactive intermediates. We demonstrate the applicability of this method as a one-pot conversion of aldehydes to esters for a broad range of aldehyde and alcohol substrates. Furthermore, the anodic oxidation reactions are very clean, producing only H₂ gas as a result of cathodic reduction.
Agid:
5386187