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

Yao-Xin Wang, Zhen Wang and Xiao-Hui Yang ()
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Yao-Xin Wang: Zhuhai
Zhen Wang: Zhuhai
Xiao-Hui Yang: Zhuhai

Nature Communications, 2024, vol. 15, issue 1, 1-8

Abstract: 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.

Date: 2024
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DOI: 10.1038/s41467-024-54896-6

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