Canadian journal of chemistry

Condensation of thiophenols with aryl halides using metallic copper as a reactant. Intermediation of cuprous thiophenolates

T Yamamoto, Y Sekine

Index: Yamamoto, Takakazu; Sekine, Yasuhiro Canadian Journal of Chemistry, 1984 , vol. 62, p. 1544 - 1547

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Citation Number: 71

Abstract

The reaction of thiophenol (PhSH) with metallic copper affords CuSPh and H2 through Cu- catalyzed dehydrogenative coupling of PhSH to PhSSPh and ensuing addition of PhSSPh to Cu. Condensation between thiophenols (ArSH) and aryl iodides or bromides (Ar'X) in the presence of Cu affords diaryl sulfides (ArSAr') in good or moderate yields (ArSH+ Ar'X+ Cu→ ArSAr'+ CuX+ 1/2H2). Use of alkyl iodides (RI), instead of Ar'X, affords alkyl aryl sulfides ( ...