Issue 100, 2016

Umpolung synthesis of branched α-functionalized amines from imines via photocatalytic three-component reductive coupling reactions

Abstract

A three component reductive coupling reaction of a (hetero)aromatic amine, a (hetero)aromatic aldehyde and an electron deficient olefin catalysed by eosin Y under green LED light irradiation, for the direct generation of γ-amino acid derivatives, is described. This new umpolung synthesis of amines, which exploits the high nucleophilicity of a putative α-amino radical intermediate, generated via single electron reduction of the in situ generated imine from the Hantzsch ester terminal reductant, is efficient, operationally simple, broad in scope and offers a complementary strategy to existing synthetic approaches.

Graphical abstract: Umpolung synthesis of branched α-functionalized amines from imines via photocatalytic three-component reductive coupling reactions

Supplementary files

Article information

Article type
Communication
Submitted
05 Oct 2016
Accepted
23 Nov 2016
First published
24 Nov 2016
This article is Open Access
Creative Commons BY license

Chem. Commun., 2016,52, 14434-14437

Umpolung synthesis of branched α-functionalized amines from imines via photocatalytic three-component reductive coupling reactions

A. L. Fuentes de Arriba, F. Urbitsch and D. J. Dixon, Chem. Commun., 2016, 52, 14434 DOI: 10.1039/C6CC09172E

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