Issue 6, 2012

Amidines, isothioureas, and guanidines as nucleophilic catalysts

Abstract

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

Article information

Article type
Tutorial Review
Submitted
21 Oct 2011
First published
10 Jan 2012

Chem. Soc. Rev., 2012,41, 2109-2121

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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