Palladium-catalyzed remote internal C(sp3)-H bond chlorination of alkenes
Yao-Xin Wang1,2, Zhen Wang1,2, Xiao-Hui Yang3,4,5
1Advanced Research Institute of Multidisciplinary Science, Beijing Institute of Technology, Zhuhai, Zhuhai, 519088, PR China.
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.
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