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N-Arylation of Sterically Hindered NH-Nucleophiles: Copper-Mediated Syntheses of Diverse N-Arylindole-2-carboxylates

Authors
Lee, JinyongChoi, Ji HyeShin, SeunghoonHeo, Jung-NyoungLim, Hwan Jung
Issue Date
Nov-2015
Publisher
GEORG THIEME VERLAG KG
Keywords
copper; N-arylation; indoles; copper-mediated synthesis; heterocyclic amines; metal-catalyzed
Citation
SYNTHESIS-STUTTGART, v.47, no.21, pp.3301 - 3308
Indexed
SCIE
SCOPUS
Journal Title
SYNTHESIS-STUTTGART
Volume
47
Number
21
Start Page
3301
End Page
3308
URI
https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/142884
DOI
10.1055/s-0035-1560065
ISSN
0039-7881
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.
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