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Advanced Research Institute of Multidisciplinary Science, Beijing Institute of Technology, Zhuhai, Zhuhai, 519088, PR China.
Published: December 2024
AI Article Synopsis
- C(sp)-Cl bonds play a crucial role in many biologically active compounds and can serve as points for chemical modification through various reactions
- The study introduces a method for selective chlorination of C(sp)-H bonds in alkenes using a two-step process involving isomerization and hydrochlorination, leading to benzylic and tertiary chlorides with high selectivity
- The research highlights the ability to synthesize a specific alkyl chloride from mixed isomeric alkenes found in raw petrochemical materials, which could enhance the late-stage modification of natural products and pharmaceuticals
Article Abstract
C(sp)-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)-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.
