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Palladium-catalyzed remote internal C(sp3)−H bond chlorination of alkenes
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Palladium-catalyzed remote internal C(sp3)−H bond chlorination of alkenes
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Palladium-catalyzed remote internal C(sp3)−H bond chlorination of alkenes
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Journal Article
Palladium-catalyzed remote internal C(sp3)−H bond chlorination of alkenes
2024
Overview
C(
sp
3
)–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(
sp
3
)–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.
C(sp
3
)–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. Here, the authors report a remote internal site-selective C(sp
3
)–H bond chlorination of alkenes through sequential alkene isomerization and hydrochlorination, enabling the synthesis of both benzylic and tertiary chlorides with excellent site-selectivity.
