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

Chuanzhou Tao; Weiwei Liu; Aifeng Lv; Mingming Sun; Ying Tian; Qi Wang; Jing Zhao

doi:10.1055/s-0029-1219922

LETTER

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

Chuanzhou Tao*^a, Weiwei Liu^a, Aifeng Lv^b, Mingming Sun^a, Ying Tian^a, Qi Wang^a, 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;

Abstract

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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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References

References and Notes

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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.

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