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 excellen...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.展开更多
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)+1 种基金the National Natural Science Foundation of China(22161006)the Natural Science Foundation of Shandong Province(ZR2020MB016)isgratefully acknowledged。
文摘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.
