Organocatalyzed Anodic Oxidation of Aldehydes

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 dem...

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Veröffentlicht in:Journal of the American Chemical Society 2012-08, Vol.134 (30), p.12374-12377
Hauptverfasser: Finney, Eric E, Ogawa, Kelli A, Boydston, Andrew J
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja304716r