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Synlett 2009(19): 3198-3200  
DOI: 10.1055/s-0029-1218295
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

The Use of Hydroxylamine Hydrochloride in the Chan-Lam Reaction: A Simple Access to Symmetric Diarylamines

Changfeng Zhou, Dongpeng Yang, Xiaofei Jia, Lixue Zhang, Jiang Cheng*
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, P. R. of China
Fax: +86(577)88156826; e-Mail: jiangcheng@wzu.edu.cn;
Further Information

Publication History

Received 31 July 2009
Publication Date:
21 October 2009 (online)

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Abstract

A CuBr-catalyzed coupling reaction of hydroxylamine hydrochloride and arylboronic acids is described, providing a simple and efficient methodology for the synthesis of symmetric diaryl amines. The reaction shows good functional group tolerance.

Key words

copper(I)-catalyzed - arylboronic acids - diaryl amines - hydroxylamine hydrochloride - coupling reaction

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General Procedure
Under air, a reaction tube was charged with arylboronic acid (0.2 mmol), NH2OH˙HCl (0.24 mmol), CuBr (5.7 mg, 20 mol%), K2CO3 (41.4 mg, 0.3 mmol), MeCN (2 mL) at 70 ˚C for 24 h. After the completion of the reaction, as monitored by TLC, the solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatog-raphy on a silica gel to give the product.