Photoinduced Perfluoroalkyloximation of Alkenes with Simple Perfluoroalkyl Halides
Wei Li
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi, 541004 China
These authors contributed equally to this work.
Search for more papers by this authorZhongji Li
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi, 541004 China
These authors contributed equally to this work.
Search for more papers by this authorDeliang Zhong
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi, 541004 China
These authors contributed equally to this work.
Search for more papers by this authorNianxing Wang
School of Chemistry and Pharmacy, Qilu University of Technology, Jinan, Shandong, 250353 China
Search for more papers by this authorCorresponding Author
Huaifeng Li
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi, 541004 China
E-mail: [email protected]Search for more papers by this authorWei Li
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi, 541004 China
These authors contributed equally to this work.
Search for more papers by this authorZhongji Li
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi, 541004 China
These authors contributed equally to this work.
Search for more papers by this authorDeliang Zhong
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi, 541004 China
These authors contributed equally to this work.
Search for more papers by this authorNianxing Wang
School of Chemistry and Pharmacy, Qilu University of Technology, Jinan, Shandong, 250353 China
Search for more papers by this authorCorresponding Author
Huaifeng Li
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin, Guangxi, 541004 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
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 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.
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- 10The tBuO radical could react with TMEDA radical cations or iodide ions (either through HAT from radical cations or reduction by I-) to produce tBuOH. Further efforts to understand the detailed mechanism of this method are ongoing.
