Tetrahedron

An improved protocol for synthesis of N-arylamides and benzoxazoles by the copper-catalyzed reaction of aryl halides with nitriles

DX Zhang, SK Xiang, H Hu, W Tan, C Feng, BQ Wang…

Index: Zhang, Dong-Xue; Xiang, Shi-Kai; Hu, Hao; Tan, Wen; Feng, Chun; Wang, Bi-Qin; Zhao, Ke-Qing; Hu, Ping; Yang, Hua Tetrahedron, 2013 , vol. 69, # 47 p. 10022 - 10029

Full Text: HTML

Citation Number: 8

Abstract

Abstract An improved protocol for the synthesis of N-arylamides and benzoxazoles by the copper-catalyzed reaction of aryl halides with nitriles has been developed. Use of acetaldoxime as the hydrolysis reagent instead of H 2 O facilitates the operation of the reaction. The significantly decreased amount of nitriles, along with use of weak base K 2 CO 3 instead of strong base KOH, makes this transformation atom-efficient and ...

Related Articles:

A green route for the synthesis of 2-substituted benzoxazole derivatives catalyzed by Al 3+-exchanged K10 clay

[Suresh, Dhanusu; Dhakshinamoorthy, Amarajothi; Pitchumani, Kasi Tetrahedron Letters, 2013 , vol. 54, # 48 p. 6415 - 6419]

Poly (ethylene glycol)-bound sulphonic acid as a novel catalyst for synthesis of benzoxazoles

[Chikhale, Rupesh V.; Pant, Amit M.; Menghani, Sunil S.; Wadibhasme, Pankaj G.; Khedekar, Pramod B. South African Journal of Chemistry, 2013 , vol. 66, p. 254 - 262]

Copper-catalyzed synthesis of benzoxazoles via a regioselective C− H functionalization/C− O bond formation under an air atmosphere

[Ueda, Satoshi; Nagasawa, Hideko Journal of Organic Chemistry, 2009 , vol. 74, # 11 p. 4272 - 4277]

Direct arylation of benzoxazole C–H bonds with iodobenzene diacetates

[Yu, Peng; Zhang, Guangyou; Chen, Fan; Cheng, Jiang Tetrahedron Letters, 2012 , vol. 53, # 34 p. 4588 - 4590]

Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides

[Evindar, Ghotas; Batey, Robert A. Journal of Organic Chemistry, 2006 , vol. 71, # 5 p. 1802 - 1808]

More Articles...