A General and Efficient Approach to Aryl Thiols: CuI-Catalyzed Coupling of Aryl Iodides with Sulfur and Subsequent Reduction

Yongwen Jiang*, Yuxia Qin, Siwei Xie, Xiaojing Zhang, Jinhua Dong and Dawei Ma*

*Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, Email: jiangywmail.sioc.ac.cn, madwmail.sioc.ac.cn

Y. Jiang, Y. Qin, S. Xie, X. Zhang, J. Dong, D. Ma, Org. Lett., 2009, 11, 5250-5253.

DOI: 10.1021/ol902186d

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Abstract

A CuI-catalyzed coupling reaction of aryl iodides and sulfur powder takes place in the presence of K₂CO₃ at 90°C in DMF as solvent. The coupling mixture is directly treated with NaBH₄ or triphenylphosphine to afford aryl thiols in good to excellent yields. A wide range of substituted aryl thiols that bear methoxy, hydroxyl, carboxylate, amido, keto, bromo, and fluoro groups can be synthesized.

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Key Words

Aryl Thiols, Sodium Borohydride, Triphenylphosphine

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ID: J54-Y2009-3370