A general and efficient approach to aryl thiols: CuI-catalyzed coupling of aryl iodides with sulfur and subsequent reduction.
A CuI-catalyzed coupling reaction of aryl iodides and sulfur powder takes place in the presence of K(2)CO(3) at 90 degrees C. The coupling mixture is directly treated with NaBH(4) 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 assembled through this procedure.
Jiang
Yongwen
Y
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China. jiangyw@mail.sioc.ac.cn
Qin
Yuxia
Y
Xie
Siwei
S
Zhang
Xiaojing
X
Dong
Jinhua
J
Ma
Dawei
D
D002254:Carbonates / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011188:Potassium / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013455:Sulfur / Q000737:chemistry*
D002254:Carbonates; D006847:Hydrocarbons, Iodinated; D007454:Iodides; D013438:Sulfhydryl Compounds; D013455:Sulfur; D003300:Copper; C073870:cuprous iodide; C037593:potassium carbonate; D011188:Potassium