Chemoselective acylation of benzimidazoles with phenylacetic acids under different Cu catalysts to give fused five-membered N-heterocycles or tertiary amides. Issue 37 (19th July 2016)

• Record Type: Journal Article
• Authors: Mai, Shaoyu; Zhao, Yingwei; Song, Qiuling
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 37(2016)
• Page Start: 8685
• Page End: 8690
• Publication Date: 2016-07-19
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob01167e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Chemoselective C–N bond formations via aerobic oxidative decarboxylative tandem protocols under different Cu catalysts were realized. 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(sp 2 )–H bond of benzimidazoles under the Cu(OAc)2 /K2 CO3 /BF3 ·Et2 O catalytic system, while with CuBr as the catalyst and pyridine as the base, N -acylation occurred and tertiary amides were obtained.