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Issue 37, 2016
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Chemoselective acylation of benzimidazoles with phenylacetic acids under different Cu catalysts to give fused five-membered N-heterocycles or tertiary amides

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Abstract

C–N bond formation via a copper-catalyzed aerobic oxidative decarboxylative tandem protocol was realized. The phenylacetic acids which contain ortho-X (X = F or Br) on the aromatic ring will render a fused five-membered heterocycle via a tandem aromatic nucleophilic substitution and aerobic oxidative decarboxylative acylation at the C(sp2)–H bond of benzimidazoles under the Cu(OAc)2/K2CO3/BF3·Et2O catalytic system, while with CuBr as the catalyst and pyridine as the base, N-acylation occurred and tertiary amides were obtained.

Graphical abstract: Chemoselective acylation of benzimidazoles with phenylacetic acids under different Cu catalysts to give fused five-membered N-heterocycles or tertiary amides

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Article information


Submitted
28 May 2016
Accepted
09 Jul 2016
First published
12 Jul 2016

Org. Biomol. Chem., 2016,14, 8685-8690
Article type
Paper

Chemoselective acylation of benzimidazoles with phenylacetic acids under different Cu catalysts to give fused five-membered N-heterocycles or tertiary amides

S. Mai, Y. Zhao and Q. Song, Org. Biomol. Chem., 2016, 14, 8685
DOI: 10.1039/C6OB01167E

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