Issue 37, 2018

The importance of N-heterocyclic carbene basicity in organocatalysis

Abstract

N-Heterocyclic carbenes (NHCs) are versatile species that figure prominently as catalysts. Despite their widespread use in organocatalysis, studies of the relationship between the basicity of NHCs and their catalytic ability are limited. Herein we review work on both the examination of NHC basicity as well as its impact on organocatalysis. The review is divided into three main parts: an overview of NHC basicity studies, both in solution and in the gas phase; the role of basicity in Umpolung-type catalysis; and the relationship between NHC basicity and its growing role as a Brønsted base catalyst. This review is not an exhaustive catalog of all NHC catalysis, but rather focuses on work that specifically examines and discusses the effect of NHC basicity on catalyst function.

Graphical abstract: The importance of N-heterocyclic carbene basicity in organocatalysis

Article information

Article type
Review Article
Submitted
13 Jul 2018
Accepted
29 Ago 2018
First published
07 Sep 2018

Org. Biomol. Chem., 2018,16, 8230-8244

Author version available

The importance of N-heterocyclic carbene basicity in organocatalysis

N. Wang, J. Xu and J. K. Lee, Org. Biomol. Chem., 2018, 16, 8230 DOI: 10.1039/C8OB01667D

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