Selenide Ions as Catalysts for Homo- and Crossed-Tishchenko Reactions of Expanded Scope

Simon P. Curran and Stephen J. Connon*

*School of Chemistry, Centre for Synthesis and Chemical Biology, Trinity Biomedical Sciences Institute, University of Dublin, Trinity College, Dublin 2, Ireland, Email: connonstcd.ie

S. P. Curran, S. J. Connon, Org. Lett., 2012, 14, 1074-1077.

DOI: 10.1021/ol203439g

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Abstract

For Tishchenko reactions, selenide ions are superior catalysts to previously reported thiolate analogues. These catalysts promote the disproportionation of aldehydes with increased reaction rates and broader scope at lower catalyst loadings and temperatures. Significantly improved catalyst performance was also observed in the aryl selenide mediated crossed intermolecular Tishchenko reaction.

see article for more examples

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The Thiolate-Catalyzed Intermolecular Crossed Tishchenko Reaction: Highly Chemoselective Coupling of Two Different Aromatic Aldehydes

S. P. Curran, S. J. Connon, Angew. Chem. Int. Ed., 2012, 51, 10866-10870.

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Key Words

Tishchenko Reaction, Redox Esterifications

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ID: J54-Y2012-0420