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

C Zhou, D Yang, X Jia, L Zhang, J Cheng

Index: Zhou, Changfeng; Yang, Dongpeng; Jia, Xiaofei; Zhang, Lixue; Cheng, Jiang Synlett, 2009 , # 19 p. 3198 - 3200

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Abstract

Initial studies were conducted using hydroxylamine hydrochloride (1.2 equiv) and phenylboronic acid 1a (0.2 mmol) in toluene as a model reaction under air in the presence of CuBr (20 mol%). Disappointingly, after the extensive screening of copper sources and solvents, no synthetically useful results were obtained. We realized that acid conditions provided by the hydroxylamine hydrochloride might inhibit the reaction. Thus, K 2 CO 3 was added to the reaction ...