Citation: Li Xiaobo, Zhao Juan, Liu Qian, Jiang Min, Liu Jintao. Addition of Perfluoroalkanesulfenic Acids to Alkynes and Allenes[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 183-191. doi: 10.6023/cjoc201808036 shu

Addition of Perfluoroalkanesulfenic Acids to Alkynes and Allenes

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Liu Jintao, jtliu@sioc.ac.cn
Received Date: 28 August 2018
Revised Date: 18 October 2018
Available Online: 26 January 2018
Fund Project: the National Natural Science Foundation of China 21572257Project supported by the National Natural Science Foundation of China (Nos. 21572257, 21502213)the National Natural Science Foundation of China 21502213

Figures(3)

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.
- perfluoroalkanesulfenic acid,
- alkyne,
- allene,
- perfluoroalkyl alkenyl sulfoxide,
- addition reaction
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