Amidines, isothioureas, and guanidines as nucleophilic catalysts

James E Taylor, Steven D Bull, Jonathan M J Williams

Research output: Contribution to journalArticle

274 Citations (Scopus)
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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.
Original languageEnglish
Pages (from-to)2109-2121
Number of pages13
JournalChemical Society Reviews
Volume41
Issue number6
DOIs
Publication statusPublished - 2012

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