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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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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