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

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, Angew. Chem. Int. Ed., 2012, 51, 10866-10870.

DOI: 10.1002/anie.201206343 (free Supporting Information)


Abstract

A readily prepared, inexpensive thiolate-based catalyst enables a highly selective, atom-economical crossed Tishchenko disproportionation of ortho-substituted benzaldehydes with other aromatic aldehydes. The methodology is of exceptionally wide scope and exhibits a high functional-group tolerance.

see article for more examples

proposed catalytic cycle



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

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


Key Words

disproportionation, esters, hydride transfer, thiols, Tishchenko reaction, redox esterifications


ID: J06-Y2012-0610