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 iyn 2020
First published
11 iyn 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements