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Unactivated C(sp3)-H functionalization via vinyl cations

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Abstract

Direct functionalization of inert C(sp3)–H bonds is a topic of immense contemporary interest and exceptional value in organic synthesis. The recent research has established a novel and practical protocol which features the engagement of vinyl cation species to functionalize C(sp3)–H bonds. The discussion of the topic is arranged by the strategies to generate the reactive intermediates, including ionization of vinyl triflates, addition of electrophiles to alkynes, tandem cyclization of enynes or diynes, and decomposition of β-hydroxy-α-diazo ketones. This review closes with a personal perspective on the dynamic research area of unactivated C(sp3)–H functionalization via vinyl cations. Hopefully, it will provide timely illumination and beneficial guidance for organic chemists who are interested in this area. Meanwhile continued development of the field is strongly anticipated in the future.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21772161, 21828102), the Natural Science Foundation of Fujian Province (2019J02001), the President Research Funds from Xiamen University (20720180036), NFFTBS (J1310024), the Foundation of Wenzhou Science & Technology Bureau (ZY2020027), and the Science & Technology Co-operation Program of Xiamen (3502Z20183015).

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Key Laboratory of Environmental Functional Materials Technology and Application of Wenzhou City, College of Chemistry & Materials Engineering, Institute of New Materials & Industry Technology, Wenzhou University, Wenzhou, 325035, China

    Xi-Jia Liu, Conghui Tang & Peng-Cheng Qian

  2. Key Laboratory of Chemical Biology of Fujian Province, State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China

    Yin Xu & Long-Wu Ye

  3. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China

    Long-Wu Ye

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  1. Xi-Jia Liu
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  2. Yin Xu
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  4. Peng-Cheng Qian
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Correspondence to Peng-Cheng Qian or Long-Wu Ye.

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Liu, XJ., Xu, Y., Tang, C. et al. Unactivated C(sp3)-H functionalization via vinyl cations. Sci. China Chem. 65, 20–30 (2022). https://doi.org/10.1007/s11426-021-1117-2

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