Issue 3, 2017

Organocatalytic activation of isocyanides: N-heterocyclic carbene-catalyzed enaminone synthesis from ketones

Abstract

The first example of the use of an N-heterocyclic carbene (NHC) as an organocatalyst for the activation of isocyanides was demonstrated. On the basis of previous reports on the interaction between NHCs and isocyanides, we developed a catalytic cycle involving transient imidoyl intermediate. The reaction of ketones with isocyanides produced the corresponding enaminones with high efficiency. Control experiments suggested a novel role for the carbene in the activation of isocyanides, and a proton transfer process was found to be crucial for the generation of two activated species in the catalytic cycle. Various enaminones, some of which are not easily accessible by other methods, were synthesized in excellent yields. This study clearly demonstrates the potential of the nucleophilic activation of isocyanides in the expansion of their reactivity scope.

Graphical abstract: Organocatalytic activation of isocyanides: N-heterocyclic carbene-catalyzed enaminone synthesis from ketones

Supplementary files

Article information

Article type
Edge Article
Submitted
01 Dec 2016
Accepted
19 Dec 2016
First published
20 Dec 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2017,8, 2401-2406

Organocatalytic activation of isocyanides: N-heterocyclic carbene-catalyzed enaminone synthesis from ketones

J. Kim and S. H. Hong, Chem. Sci., 2017, 8, 2401 DOI: 10.1039/C6SC05266E

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