Vanadium-Mediated Carbon Isotope Exchange of Terminal Alkenes
Year: 2025
Type: article
Abstract: The incorporation of carbon isotopes into bioactive compounds is of great importance in chemistry, biology, and medicine. Especially valuable are catalytic procedures that rely on a limited collection of available labeled materials. Recently we introduced a conceptually novel solution to carbon isotope exchange (CIE) for terminal olefins based on the preference of V alkylidenes for degenerate metathesis. However, the previous report utilized a V catalyst that suffered from functional group tolerance due to the high electrophilicity of the V center, making it impractical for biological compounds. Herein, we utilized V catalysts containing electron-donating groups to overcome those challenges. We utilize isotopically labeled substituted styrene as a labeled ═ 13 CH 2 moiety source, prepared from 13 C-labeled iodomethane. The isotope source can be easily removed from the reaction mixture, recovered, and reused. A diverse range of terminal alkenes, including bioactive molecules, were tested to showcase the capabilities and limitations of the developed method.
DOI: 10.1021/jacs.5c05880
Institution: Florida International University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W4411081803