Direct Carbon Isotope Exchange through Decarboxylative Carboxylation

• DOI: 10.1021/jacs.8b12035
• Publication Date: 2019-01-03T20:30:01Z
• Authors: Cian Kingston; Michael A. Wallace; Alban J. Allentoff; Justine N. deGruyter; Jason S. Chen; Sharon X. Gong; Samuel Bonacorsi; Phil S. Baran
• Keywords: Carboxylation; Kinetic isotope effect; Carbon-14; Decarboxylation; Carbon fibers

A two-step degradation–reconstruction approach to the carbon-14 radiolabeling of alkyl carboxylic acids is presented. Simple activation via redox-active ester formation was followed by nickel-mediated decarboxylative carboxylation afford a range complex compounds with ample isotopic incorporations for drug metabolism and pharmacokinetic studies. The practicality operational simplicity protocol were demonstrated its use in an industrial setting.