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: connons
tcd.ie
S. P. Curran, S. J. Connon, Angew. Chem. Int. Ed., 2012, 51, 10866-10870.
DOI: 10.1002/anie.201206343
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
