Palladium-catalyzed remote internal C(sp<sup>3</sup>)-H bond chlorination of alkenes.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 39639004.
- Also identified by DOI 10.1038/s41467-024-54896-6 and PMC identifier 11621330.
- Licence recorded as CC BY-NC-ND.
- Because redistribution is not established, this page shows the abstract only. Follow the links below for the full text.
Abstract
C(sp<sup>3</sup>)-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<sup>3</sup>)-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.