Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


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