Unusual Single Electron Transfer Reactions between Alkenes and Iodine Electrophiles  

作　　者：Zhengzhao Lou Jingyu Hu Chuanfa Ni Xiu Wang Jinbo Hu 

机构地区：[1]Key Laboratory of Organofluorine Chemistry,Shanghai Institute of Organic Chemistry,University of Chinese Academy of Sciences,Chinese Academy of Sciences,345 Ling Ling Road,Shanghai,200032 China [2]School of Physical Science and Technology,ShanghaiTech University,100 Haike Road,Shanghai,201210 China

出　　处：《Chinese Journal of Chemistry》2024年第5期471-477,共7页中国化学（英文版）

基　　金：supported by National Key Research and Development Program of China(2021YFF0701700);the National Natural Science Foundationof China(22271299 and 22261132514).

摘　　要：The electrophilic addition to an alkene with an electrophile has been widely studied and applied in organic synthesis.The organic chemistry textbook describes the classical reaction between an alkene and an iodine electrophile(such as elemental iodine and N-iodosuccinimide(NIS))as a typical ionic reaction,in which an iodonium ion is formed and then attacked by a nucleophile.However,in this article,we report a new and unusual reaction mode between an alkene and NIS;that is,a single electron transfer(SET)process occurs between these two reactants by forming an electron-donor acceptor complex.Not only does this unusual single electron transfer reaction between an alkene and NIS add fundamentally important knowledge to organic chemistry,it also provides a valuable synthetic method as the new SET reaction mode with opposite regioselectivity as compared with the traditional ionic mode.

关 键 词：Electrophilic addition Radical ions Reaction mechanisms ALKENES FLUORINE 

分 类 号：O62[理学—有机化学]