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Synthesis 2015; 47(21): 3301-3308
DOI: 10.1055/s-0035-1560065
DOI: 10.1055/s-0035-1560065
paper
N-Arylation of Sterically Hindered NH-Nucleophiles: Copper-Mediated Syntheses of Diverse N-Arylindole-2-carboxylates
Further Information
Publication History
Received: 01 June 2015
Accepted after revision: 07 July 2015
Publication Date:
20 August 2015 (online)
Abstract
Indole-carboxylates are N-arylated with 2-bromopyridines using stoichiometric copper(II) oxide/potassium carbonate to give various N-(2-pyridyl)-substituted indole-2-carboxylates and with bromobenzenes using stoichiometric copper(I) iodide/N,N′-dimethylethylenediamine to give various N-(substituted phenyl)-substituted indole-2-carboxylates. These results expand the scope of metal-catalyzed N-arylation using heterocyclic amines with steric bulk and weak nucleophilicity.
Key words
copper - N-arylation - indoles - copper-mediated synthesis - heterocyclic amines - metal-catalyzedSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560065.
- Supporting Information
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For reviews of metal-catalyzed N-arylation of indoles, see
For reviews and selected reports, see: