Volume 42, Issue 5 pp. 471-477
Concise Report

Unusual Single Electron Transfer Reactions between Alkenes and Iodine Electrophiles

Zhengzhao Lou

Zhengzhao Lou

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

School of Physical Science and Technology, ShanghaiTech University, 100 Haike Road, Shanghai, 201210 China

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Jingyu Hu

Jingyu Hu

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

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Chuanfa Ni

Chuanfa Ni

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

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Xiu Wang

Xiu Wang

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

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Jinbo Hu

Corresponding Author

Jinbo Hu

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

School of Physical Science and Technology, ShanghaiTech University, 100 Haike Road, Shanghai, 201210 China

E-mail: [email protected]Search for more papers by this author
First published: 01 November 2023

These authors contributed equally to this work.

Dedicated to the Memory of Professor Xiyan Lu.

Comprehensive Summary

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.image

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