The Thiolate-Catalyzed Intermolecular Crossed Tishchenko Reaction: Highly Chemoselective Coupling of Two Different Aromatic Aldehydes†
Simon P. Curran
Centre for Synthesis and Chemical Biology, Trinity, Biomedical Sciences Institute, School of Chemistry, The University of Dublin, Trinity College, Dublin 2 (Ireland)
Search for more papers by this authorCorresponding Author
Prof. Stephen J. Connon
Centre for Synthesis and Chemical Biology, Trinity, Biomedical Sciences Institute, School of Chemistry, The University of Dublin, Trinity College, Dublin 2 (Ireland)
Centre for Synthesis and Chemical Biology, Trinity, Biomedical Sciences Institute, School of Chemistry, The University of Dublin, Trinity College, Dublin 2 (Ireland)Search for more papers by this authorSimon P. Curran
Centre for Synthesis and Chemical Biology, Trinity, Biomedical Sciences Institute, School of Chemistry, The University of Dublin, Trinity College, Dublin 2 (Ireland)
Search for more papers by this authorCorresponding Author
Prof. Stephen J. Connon
Centre for Synthesis and Chemical Biology, Trinity, Biomedical Sciences Institute, School of Chemistry, The University of Dublin, Trinity College, Dublin 2 (Ireland)
Centre for Synthesis and Chemical Biology, Trinity, Biomedical Sciences Institute, School of Chemistry, The University of Dublin, Trinity College, Dublin 2 (Ireland)Search for more papers by this authorFinancial support from the European Research Council is gratefully acknowledged.
Graphical Abstract
Crossed products: Ortho-substituted benzaldehydes react with other aromatic aldehydes in a highly selective, atom-economical Tishchenko disproportionation (see scheme) in the presence of a readily prepared, inexpensive thiolate-based catalyst. The methodology is of exceptionally wide scope and exhibits a high functional-group tolerance.
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