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Issue 6, 2012
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Amidines, isothioureas, and guanidines as nucleophilic catalysts

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Over the last ten years there has been a huge increase in development and applications of organocatalysis in which the catalyst acts as a nucleophile. Amidines and guanidines are often only thought of as strong organic bases however, a number of small molecules containing basic functional groups have been shown to act as efficient nucleophilic catalysts. This tutorial review highlights the use of amidine, guanidine, and related isothiourea catalysts in organic synthesis, as well as the evidence for the nucleophilic nature of these catalysts. The most common application of these catalysts to date has been in acyl transfer reactions, although the application of these catalysts towards other reactions is an increasing area of interest. In this respect, amidine and guanidine derived catalysts have been shown to be effective in catalysing aldol reactions, Morita–Baylis–Hillman reactions, conjugate additions, carbonylations, methylations, silylations, and brominations.

Graphical abstract: Amidines, isothioureas, and guanidines as nucleophilic catalysts

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Publication details

The article was received on 21 Oct 2011 and first published on 10 Jan 2012

Article type: Tutorial Review
DOI: 10.1039/C2CS15288F
Citation: Chem. Soc. Rev., 2012,41, 2109-2121

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    Amidines, isothioureas, and guanidines as nucleophilic catalysts

    J. E. Taylor, S. D. Bull and J. M. J. Williams, Chem. Soc. Rev., 2012, 41, 2109
    DOI: 10.1039/C2CS15288F

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