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Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (10): 1719-1722. Previous Articles     Next Articles

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含水四氢呋喃中二茂钛全氟辛基磺酸配合物催化锌粉还原二硫醚及其在合成硫代酸酯中的应用

许海南1,2，刘文奇*,3，彭丽芬1，邱仁华1，赵亚磊1，潘建高1，许新华*,1   

  1. (3湖南大学化学化工学院 长沙 410082)
    (2湖南省妇幼保健院 长沙 410008)
    (1湘南学院化学系 郴州 423000)
  • 收稿日期:2011-01-30 修回日期:2011-05-09 发布日期:2011-05-14
  • 通讯作者: 许新华 E-mail:xhx1581@21cn.com;xhx1581@yahoo.com.cn

Titanocene Perfluorooctanesulfonate-Catalyzed Reductive Cleavage of S—S Bond by Zinc in Commercial Tetrahedron and Its Application in Synthesis of Thioesters

Xu Hainan1,2 Liu Wenqi*,3 Peng Lifen1 Qiu Renhua1 Zhao Yalei1 Pan Jiangao1 Xu Xinhua*,1   

  1. (1 College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082)
    (2 Maternal and Child Health Hospital of Hunan Province, Changsha 410008)
    (3 Department of Chemistry, Xiangnan University, Chenzhou 42300)
  • Received:2011-01-30 Revised:2011-05-09 Published:2011-05-14

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In the presence of 5.0 mol% titanocene perfluorooctanesulfonate, reductive cleavage S—S bond by zinc at room temperature led to nucleophilic sulfur anion species, which reacted with acid anhydrides (α-bromocarbonyl compounds) to afford thioesters (α-arylthiocarbonyl compounds) in good to excellent yields. The catalyzed mechanism was discussed.

Key words: titanocene bis(perfluorooctanesulfonate)s, zinc, disulfide, thioester, α-arylthioesters