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An overview of N-heterocyclic carbenes

Nature volume 510, pages 485–496 (2014)Cite this article

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Abstract

The successful isolation and characterization of an N-heterocyclic carbene in 1991 opened up a new class of organic compounds for investigation. From these beginnings as academic curiosities, N-heterocyclic carbenes today rank among the most powerful tools in organic chemistry, with numerous applications in commercially important processes. Here we provide a concise overview of N-heterocyclic carbenes in modern chemistry, summarizing their general properties and uses and highlighting how these features are being exploited in a selection of pioneering recent studies.

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Figure 1: Major applications of NHCs.
Figure 2: Structural features of NHCs.
Figure 3: Major applications of NHCs coordinated to transition metals.
Figure 4: NHCs as ligands in ruthenium-catalysed olefin metathesis.
Figure 5: NHCs as ligands in palladium-catalysed cross-coupling.
Figure 6: NHC coordination to nanoparticles and metal surfaces.
Figure 7: Major applications of NHCs coordinated to p-block elements.
Figure 8: Stabilization of p-block species by NHCs.
Figure 9: Major applications of NHCs in organocatalysis.
Figure 10: Major NHC-catalysed reactions of aldehydes.
Figure 11: NHC-catalysed β-functionalization of saturated esters.

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Acknowledgements

We thank the European Research Council under the European Community’s Seventh Framework Program (FP7 2007-2013)/ERC grant agreement number 25936, the Deutsche Forschungsgemeinschaft (Leibniz Award and SFB 858), the Alexander von Humboldt Foundation (to M.N.H.) and the Fonds der Chemischen Industrie (to M.S.) for financial support.

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  1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany,

    Matthew N. Hopkinson, Christian Richter, Michael Schedler & Frank Glorius

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  1. Matthew N. Hopkinson
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All authors worked together to outline the content of the review and define its scope. The text was primarily written by M.N.H. and F.G. with contributions from all authors. The figures were prepared by M.N.H., C.R. and M.S. Editing of the manuscript, figures and references was done by all authors.

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Correspondence to Frank Glorius.

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Hopkinson, M., Richter, C., Schedler, M. et al. An overview of N-heterocyclic carbenes. Nature 510, 485–496 (2014). https://doi.org/10.1038/nature13384

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