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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 (free Supporting Information)



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Abstract

A CuI-catalyzed coupling reaction of aryl iodides and sulfur powder takes place in the presence of K2CO3 at 90C 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


ID: J54-Y2009-3370