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Synlett 2011(1): 134-138  
DOI: 10.1055/s-0030-1259079
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Ligand-Free Copper-Catalyzed Synthesis of Diaryl Thioethers from Aryl Halides and Thioacetamide

Chuanzhou Tao*a,b, Aifeng Lvb, Nan Zhaoa, Shuai Yanga, Xiaolang Liua, Jian Zhoua, Weiwei Liua, 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;
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Publikationsverlauf

Received 18 September 2010
Publikationsdatum:
07. Dezember 2010 (online)

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Abstract

Diaryl thioethers can be prepared via a copper-catalyzed cross-coupling between aryl halides and thioacetamide using Cs2CO3 as a base and DMSO-H2O as a solvent at 120 ˚C.

Key words

copper - catalysis - cross-coupling - diaryl thioether - aryl­ation - thioacetamide

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11

Coupling of Aryl Halides with Thioacetamide - General Procedure An oven-dried Schlenk tube was charged with CuI (18 mg, 10 mol%), MeCSNH2 (75 mg, 1.0 mmol), Cs2CO3 (978 mg, 3.0 mmol), and aryl halide (2.5 mmol). The tube was evacuated and backfilled with argon. Then, DMSO-H2O (0.5 mL/0.25 mL) were added under argon. The tube was sealed, and the reaction mixture was stirred at 120 ˚C for
24-36 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.