Imines as acceptors and donors in N-heterocyclic carbene (NHC) organocatalysis

Das, TK and Biju, AT (2020) Imines as acceptors and donors in N-heterocyclic carbene (NHC) organocatalysis. In: Chemical Communications, 56 (61). pp. 8537-8552.

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Abstract

The synthetic potential of imines as electrophiles or as a source of nucleophilic coupling partner in N-heterocyclic carbene (NHC) catalysis for the synthesis of various nitrogen heterocycles and functionalized amines is highlighted in this Feature Article. Electrophilic imines are suitable candidates for intercepting the NHC-derived acyl anions, homoenolate equivalents, and (di)enolates for the synthesis of α-amino ketones and a variety of lactam derivatives. Moreover, enamines generated from imines bearing α-hydrogen could be trapped with α,β-unsaturated acylazoliums for the synthesis of functionalized dihydropyridinones. NHCs are also useful for the umpolung of imines for the generation of aza-Breslow intermediates thus leading to the synthesis of indoles, quinolines, dihydroquinoxalines etc. A concise account of the diverse reactivity of imines in NHC catalysis has been presented.

Item Type:	Journal Article
Publication:	Chemical Communications
Publisher:	Royal Society of Chemistry
Additional Information:	The copyright for this article belongs to Royal Society of Chemistry.
Keywords:	Amines; Catalysis; Ketones, Acyl anions; Electrophiles; Enamines; Enolates; Functionalized; N-heterocyclic carbenes; Nitrogen heterocycles; Organocatalysis, Synthesis (chemical), alpha ketone derivative; alpha,beta unsaturated acylazolium derivative; amine; anion; carbene; chemical compound; dihydroquinoxaline derivative; functional group; heterocyclic compound; hydrogen; imine; indole derivative; ketone derivative; lactam derivative; nitrogen; pyridone derivative; quinoline derivative; unclassified drug, Article; catalysis; chemical interaction; chemical reaction; electrophilicity; synthesis
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	15 Feb 2023 11:15
Last Modified:	15 Feb 2023 11:15
URI:	https://eprints.iisc.ac.in/id/eprint/80255

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