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Issue 14, 2016
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25 years of N-heterocyclic carbenes: activation of both main-group element–element bonds and NHCs themselves

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Abstract

N-Heterocyclic carbenes (NHCs) are widely used ligands and reagents in modern inorganic synthesis as well as in homogeneous catalysis and organocatalysis. However, NHCs are not always innocent bystanders. In the last few years, more and more examples were reported of reactions of NHCs with main-group elements which resulted in modification of the NHC. Many of these reactions lead to ring expansion and the formation of six-membered heterocyclic rings involving insertion of the heteroatom into the C–N bond and migration of hydrides, phenyl groups or boron-containing fragments. Furthermore, a few related NHC rearrangements were observed some decades ago. In this Perspective, we summarise the history of NHC ring expansion reactions from the 1960s till the present.

Graphical abstract: 25 years of N-heterocyclic carbenes: activation of both main-group element–element bonds and NHCs themselves

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Publication details

The article was received on 19 Oct 2015, accepted on 02 Dec 2015 and first published on 07 Dec 2015


Article type: Perspective
DOI: 10.1039/C5DT04106F
Dalton Trans., 2016,45, 5880-5895

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    25 years of N-heterocyclic carbenes: activation of both main-group element–element bonds and NHCs themselves

    S. Würtemberger-Pietsch, U. Radius and T. B. Marder, Dalton Trans., 2016, 45, 5880
    DOI: 10.1039/C5DT04106F

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