Photoinduced Perfluoroalkyloximation of Alkenes with Simple Perfluoroalkyl Halides  

作　　者：Wei Li Zhongji Li Deliang Zhong Nianxing Wang Huaifeng Li 

机构地区：[1]State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources,School of Chemistry and Pharmaceutical Sciences,Guangxi Normal University,Guilin,Guangxi 541004,China [2]School of Chemistry and Pharmacy,Qilu University of Technology,Jinan,Shandong 250353,China

出　　处：《Chinese Journal of Chemistry》2024年第18期2217-2222,共6页中国化学（英文版）

基　　金：support of this work by the Guangxi Natural Science Foundation of China(2020GXNSFAA297213);the Guangxi Science and Technology Base and Special Talents(AD21075017);the National Natural Science Foundation of China(22161006);the Natural Science Foundation of Shandong Province(ZR2020MB016)isgratefully acknowledged。

摘　　要：In this paper,the difunctionalizative perfluoroalkyloximation of alkenes has been developed for the first time.This photochemical method allows for the synthesis of various perfluoroalkyl ethanone oximes with excellent regioselectivity and good functional group tolerance.Our method employs the most common perfluoroalkyl source,perfluoroalkyl iodides,as Rf reagents.Besides long-chain perfluoroalkyl groups,this approach could be extended to incorporating additional groups,including trifluoromethyl,difluoromethyl,sulfonyl,and malonate,selectively into olefins,resulting in a range ofβ-substituted ethanone oximes.Notably,the potential of this method in the Fukuyama indole synthesis,generating novel 2-perfluoroalkylated 3-(α-oximidobenzyl)indoles via a radical cascade mechanism with 2-vinylphenylacryloyl isocyanate as the radical acceptor,presents a compelling avenue for drug synthesis.The protocol is efficient,scalable,and useful for late-stage modification of bioactive molecules.

关 键 词：Perfluoroalkyloximation RADICAL Fukuyama indole synthesis Difunctionalization EDA complex Regioselectivity PHOTOCHEMISTRY ALKENES 

分 类 号：O62[理学—有机化学]