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Palladium-catalyzed remote internal C(sp3)−H bond chlorination of alkenes

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  • Yao-Xin Wang

    (Zhuhai
    Beijing Institute of Technology)

  • Zhen Wang

    (Zhuhai
    Beijing Institute of Technology)

  • Xiao-Hui Yang

    (Zhuhai
    Beijing Institute of Technology
    Nankai University)

Abstract

C(sp3)–Cl bonds are present in numerous biologically active molecules and can also be used as a site for diversification by substitution or cross-coupling reactions. Herein, we report a remote internal site-selective C(sp3)–H bond chlorination of alkenes through sequential alkene isomerization and hydrochlorination, enabling the synthesis of both benzylic and tertiary chlorides with excellent site-selectivity. This transformation offers exciting possibilities for the late-stage chlorination of derivatives of natural products and pharmaceuticals. We also demonstrate the regioconvergent synthesis of a single alkyl chloride from unrefined mixtures of isomeric alkenes, which can be extracted directly from petrochemical sources.

Suggested Citation

  • Yao-Xin Wang & Zhen Wang & Xiao-Hui Yang, 2024. "Palladium-catalyzed remote internal C(sp3)−H bond chlorination of alkenes," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-54896-6
    DOI: 10.1038/s41467-024-54896-6
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    References listed on IDEAS

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    1. Amanda J. Hickman & Melanie S. Sanford, 2012. "High-valent organometallic copper and palladium in catalysis," Nature, Nature, vol. 484(7393), pages 177-185, April.
    2. Ye-Wei Chen & Yang Liu & Han-Yu Lu & Guo-Qiang Lin & Zhi-Tao He, 2021. "Palladium-catalyzed regio- and enantioselective migratory allylic C(sp3)-H functionalization," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
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