Jump to main content
Jump to site search

Issue 61, 2020
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Article information


Submitted
07 May 2020
Accepted
11 Jun 2020
First published
11 Jun 2020

Chem. Commun., 2020,56, 8537-8552
Article type
Feature Article

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

Social activity

Search articles by author

Spotlight

Advertisements