Photoinduced Perfluoroalkyloximation of Alkenes with Simple Perfluoroalkyl Halides
Wei Li , Zhongji Li , Deliang Zhong , Nianxing Wang , Huaifeng Li
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (18) : 2217 -2222.
Photoinduced Perfluoroalkyloximation of Alkenes with Simple Perfluoroalkyl Halides
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 R f 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 of β-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.
Perfluoroalkyloximation / Radical / Fukuyama indole synthesis / Difunctionalization / EDA complex / Regioselectivity / Photochemistry / Alkenes
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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