Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 183-191.DOI: 10.6023/cjoc201808036 Previous Articles     Next Articles

Special Issue: 庆祝陈庆云院士九十华诞 元素有机化学合辑2018-2019

Articles

全氟烷基次磺酸与炔烃和联烯的加成反应

李晓波, 赵娟, 刘倩, 蒋敏, 刘金涛   

  1. 中国科学院上海有机化学研究所 上海 200032
  • 收稿日期:2018-08-28 修回日期:2018-10-18 出版日期:2019-01-25 发布日期:2018-10-26
  • 通讯作者: 刘金涛 E-mail:jtliu@sioc.ac.cn
  • 基金资助:

    国家自然科学基金(Nos.21572257,21502213)资助项目.

Addition of Perfluoroalkanesulfenic Acids to Alkynes and Allenes

Li Xiaobo, Zhao Juan, Liu Qian, Jiang Min, Liu Jintao   

  1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2018-08-28 Revised:2018-10-18 Online:2019-01-25 Published:2018-10-26
  • Contact: 10.6023/cjoc201808036 E-mail:jtliu@sioc.ac.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21572257, 21502213).

The addition reaction of perfluoroalkanesulfenic acids, in-situ formed from imines, to alkynes and allenes were investigated. A series of perfluoroalkyl alkenyl sulfoxides were synthesized. Markovnikov adducts were obtained in good to excellent yields from the reactions of aryl or alkyl-substituted alkynes with perfluoroalkanesulfenic acids under mild conditions. However, the reaction of terminal alkynes containing an electron-withdrawing group afforded Michael-type adducts in good yields. The addition reaction of electron-rich allenes took place at the double bond with less steric hindrance, while the double bond connecting an electron-withdrawing group was the prior reaction site in the case of electron-deficient allenes.

Key words: perfluoroalkanesulfenic acid, alkyne, allene, perfluoroalkyl alkenyl sulfoxide, addition reaction