全氟烷基次磺酸与炔烃和联烯的加成反应
收稿日期: 2018-08-28
修回日期: 2018-10-18
网络出版日期: 2018-10-26
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
Received date: 2018-08-28
Revised date: 2018-10-18
Online published: 2018-10-26
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21572257, 21502213).
李晓波 , 赵娟 , 刘倩 , 蒋敏 , 刘金涛 . 全氟烷基次磺酸与炔烃和联烯的加成反应[J]. 有机化学, 2019 , 39(1) : 183 -191 . DOI: 10.6023/cjoc201808036
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.
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