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Synlett 2010(9): 1355-1358  
DOI: 10.1055/s-0029-1219922
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Room-Temperature Copper-Catalyzed Synthesis of Primary Arylamines from Aryl Halides and Aqueous Ammonia

Chuanzhou Tao*a, Weiwei Liua, Aifeng Lvb, Mingming Suna, Ying Tiana, Qi Wanga, Jing Zhao*b
a School of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, P. R. of China
Fax: +86(518)85895121; e-Mail: cztao@mail.ustc.edu.cn;
b State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing 210093, P. R. of China
Fax: +86(25)83592672; e-Mail: jingzhao@nju.edu.cn;
Further Information

Publication History

Received 11 February 2010
Publication Date:
06 May 2010 (online)

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Abstract

Primary arylamines can be prepared via a copper-catalyzed cross-coupling between aryl halides and aqueous ammonia using K3PO4 as a base and DMF as a solvent at room temperature.

Key words

copper - catalysis - cross-coupling - room temperature - aqueous ammonia - primary arylamine

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9

Coupling of Aryl Halides with Aqueous Ammonia at Room Temperature - General Procedure An oven-dried Schlenk tube was charged with CuI (18 mg, 10 mol%), K3PO4 (424 mg, 2.0 mmol), and aryl halide
(1.0 mmol). The tube was evacuated and backfilled with nitrogen. Then, aq NH3 (6.5 mmol, 0.5 mL) and DMF (1.0 mL) were added under nitrogen. The tube was sealed, and the reaction mixture was stirred at r.t. for 36-48 h. The reaction mixture was quenched with H2O, extracted with Et2O, and dried over anhyd MgSO4. The solvents were removed under vacuum, and the residue was purified by column chromatography (silica gel, EtOAc-PE) to afford the product.