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N-Heterocyclic Carbenes in Organocatalysis

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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

The use of N-heterocyclic carbenes (NHCs) to promote organocatalytic transformations has rapidly expanded in recent years, building upon the classic use of these compounds to generate acyl anion equivalents from aldehydes. This chapter gives an overview of the recent progress made in this area, describing the use of NHCs to generate synthetic intermediates from a range of readily accessible starting materials and recent developments in their reactivity. The reaction of an NHC can result in the formation of a range of d1, d2 and d3 synthons (acyl anion, azolium enol or enolate, and azolium homoenolate intermediates) or an electrophilic a1 acylazolium species, with typical processes that proceed through each of these intermediates described. The use of NHCs to participate in stereoselective reaction processes within each of these areas is also described, with an emphasis upon a mechanistic understanding of these processes given where appropriate.

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Authors and Affiliations

  1. EaStCHEM School of Chemistry, University of St Andrews, St Andrews, KY16 9ST, UK

    Andrew D. Smith

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  1. Craig D. Campbell
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  2. Kenneth B. Ling
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  3. Andrew D. Smith
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Correspondence to Andrew D. Smith .

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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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Campbell, C.D., Ling, K.B., Smith, A.D. (2010). N-Heterocyclic Carbenes in Organocatalysis. 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_12

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