Electrocatalytic oxidative cleavage of electron-deficient substituted stilbenes in acetonitrile-water employing a new high oxidation potential electrocatalyst. An electrochemical equivalent of ozonolysis

Xin Wu; Anthony P Davis; Albert J Fry

doi:10.1021/ol7026416

Electrocatalytic oxidative cleavage of electron-deficient substituted stilbenes in acetonitrile-water employing a new high oxidation potential electrocatalyst. An electrochemical equivalent of ozonolysis

Org Lett. 2007 Dec 20;9(26):5633-6. doi: 10.1021/ol7026416. Epub 2007 Nov 30.

Authors

Xin Wu¹, Anthony P Davis, Albert J Fry

Affiliation

¹ Chemistry Department, Wesleyan University, Middletown, Connecticut 06459, USA.

PMID: 18047368
DOI: 10.1021/ol7026416

Abstract

A series of symmetrical and unsymmetrical stilbenes bearing two or more strong electron-withdrawing groups were oxidatively cleaved to the corresponding aldehydes in high yield by electrocatalytic anodic oxidation in aqueous acetonitrile employing a new high oxidation potential triphenylamine electrocatalyst. The oxidations apparently involve the corresponding 1,2-diols, which are also converted to aldehydes in high yield under the same conditions.