Rhodium-Catalyzed Synthesis of Diaryl Sulfides Using Aryl Fluorides and Sulfur/Organopolysulfides

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• 作者：Mieko Arisawa ; Takuya Ichikawa ; Masahiko Yamaguchi
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：October 19, 2012
• 年：2012
• 卷：14
• 期：20
• 页码：5318-5321
• 全文大小：239K
• 年卷期：v.14,no.20(October 19, 2012)
• ISSN：1523-7052

文摘

Substituted pentafluorobenzenes react with sulfur to give bis(4-substituted 2,3,5,6-tetrafluorophenyl) sulfides in the presence of RhH(PPh₃)₄, 1,2-bis(diphenylphosphino)benzene (dppBz), and tributylsilane. The reaction proceeds efficiently between room temperature and 80 掳C. A comparative study of the reactivities of an organic trisulfide and a tetrasulfide showed notable substrate specificity. Di-tert-butyl tetrasulfide reacted with reactive aryl monofluorides and substituted pentafluorobenzenes. Di-tert-butyl trisulfide reacted with aryl monofluorides. The reactivity was explained on the basis of the difference in S鈥揝 bond energy.