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N-Heterocyclic Carbene Complexes: Decomposition Pathways

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N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis

Part of the book series: Catalysis by Metal Complexes ((CMCO,volume 32))

Abstract

N-heterocyclic carbenes, and their derivatives, are powerful donor ligands that form strong M–NHC bonds, particularly with late transition metals. Interest in these species has largely focused on their application as ligands in catalysis, in which they have shown some promise. However, they have not had the impact originally anticipated; NHCs undergo a number of processes that lead to catalyst deactivation and in the following chapter the range of deactivation reactions that have been reported will be discussed. By far the most detrimental deactivation process uncovered to date is reductive elimination, in which the NHC is lost as an imidazolium salt and the metal centre is reduced. This decomposition pathway is discussed in some detail and its impact on catalysis is put in context. Nevertheless, as apparent from some of the following discussion, the opportunity exists for an imaginative approach to the problem of catalyst decomposition, and it is possible to develop novel synthetic chemistry utilising these reaction pathways.

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Authors and Affiliations

  1. School of Chemistry, Cardiff University, Main Building, Park Place, CF10 3AT, Cardiff, UK

    Kingsley J. Cavell

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  1. Kingsley J. Cavell
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  2. Adrien T. Normand
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Correspondence to Kingsley J. Cavell .

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Editors and Affiliations

  1. School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, United Kingdom

    Catherine S.J. Cazin

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Cavell, K.J., Normand, A.T. (2010). N-Heterocyclic Carbene Complexes: Decomposition Pathways. In: Cazin, C. (eds) N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis. Catalysis by Metal Complexes, vol 32. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-2866-2_13

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