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Synlett 2010(19): 2891-2894  
DOI: 10.1055/s-0030-1259012
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Preparation of Aryl Sulfides Using Palladium Catalysis under Mild Conditions

Tatsuo Okauchi*, Kouji Kuramoto, Mitsuru Kitamura
Department of Applied Chemistry, Kyushu Institute of Technology, 1-1 Sensui-cho, Tobata, Kitakyushu, 804-8550, Japan
Fax: +81(93)8843314; e-Mail: okauchi@che.kyutech.ac.jp;
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Publication History

Received 16 September 2010
Publication Date:
22 October 2010 (online)

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Abstract

A convenient method for C-S cross-coupling of aryl bromides with various thiols has been developed that involves the use of a 1,1′-bis(diphenylphosphino)ferrocene (DPPF)-ligated palladium complex with N,N-diisopropylethylamine (DIPEA) as the base. This coupling is tolerant of a wide range of functional groups, including hydroxy, amino, cyano, nitro, formyl, and carboxyl groups.

Key words

palladium - thiols - cross-coupling - C-S bond formation - sulfide

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Typical Experimental Procedure: To a solution of [Pd2(dba)3] (9.2 mg, 0.010 mmol) and DPPF (11.1 mg, 0.020 mmol) in toluene (1.0 mL) were added bromobenzene (0.11 mL, 1.0 mmol), DIPEA (0.19 mL, 1.1 mmol) and octanethiol (0.17 mL, 1.0 mmol) at r.t. The solution was stirred under reflux for 3 h then cooled to r.t. The reaction was quenched by addition of H2O and extracted with EtOAc (3 × 10 mL), and the combined organic layers were washed with brine, dried (Na2SO4), and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chroma-tography on silica gel to afford octyl phenyl sulfide (222.3 mg, quantitative).