Organic letters

Iron-catalyzed 2-arylbenzoxazole formation from o-nitrophenols and benzylic alcohols

M Wu, X Hu, J Liu, Y Liao, GJ Deng

Index: Wu, Mingyue; Hu, Xiong; Liu, Juan; Liao, Yunfeng; Deng, Guo-Jun Organic Letters, 2012 , vol. 14, # 11 p. 2722 - 2725

Full Text: HTML

Citation Number: 44

Abstract

The iron-catalyzed 2-arylbenzoxazole formation from o-nitrophenols and benzylic alcohols using hydrogen transfer is described. Various 2-arylbenzoxazoles were selectively obtained in good to excellent yields. The reaction tolerated a wide range of functionalities. The alcohol oxidation, nitro reduction, condensation, and dehydrogenation were realized in a cascade without external reducing reagent and oxidant.

~82%

~84%

~80%

~76%

~82%

~76%

~75%

~77%

A green route for the synthesis of 2-substituted benzoxazole...

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

Poly (ethylene glycol)-bound sulphonic acid as a novel catal...

[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 regioselect...

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

Direct arylation of benzoxazole C–H bonds with iodobenzene d...

[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 benzothi...

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