Issue 61, 2020

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

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.

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

Article information

Article type
Feature Article
Submitted
07 May 2020
Accepted
11 Jun 2020
First published
11 Jun 2020

Chem. Commun., 2020,56, 8537-8552

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

T. K. Das and A. T. Biju, Chem. Commun., 2020, 56, 8537 DOI: 10.1039/D0CC03290E

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