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Unexpected catalysis: aprotic pyridinium ions as active and recyclable Brønsted acid catalysts in protic media

Barbara Procuranti and Stephen J. Connon*

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

B. Procuranti, S. J. Connon, Org. Lett., 2008, 10, 4935-4938.

DOI: 10.1021/ol802008m (free Supporting Information)


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Abstract

Simple pyridinium salt derivatives unexpectedly catalyze highly efficient acetalizations of aldehydes at ambient temperature. The aprotic catalyst promotes the formation of benzaldehyde dimethyl acetal at low  loadings more efficiently than a protic Brønsted acid catalyst with a pKa of 2.2. The ionic catalyst can be readily recovered by precipitation and reused without loss of activity.

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Key Words

dimethyl acetals, organocatalysis


ID: J54-Y2008-3300