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Direct Carbon Isotope Exchange through Decarboxylative Carboxylation.

ABSTRACT: 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 to afford a range of complex compounds with ample isotopic incorporations for drug metabolism and pharmacokinetic studies. The practicality and operational simplicity of the protocol were demonstrated by its use in an industrial carbon-14 radiolabeling setting.

SUBMITTER: Kingston C

PROVIDER: S-EPMC7000106 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Direct Carbon Isotope Exchange through Decarboxylative Carboxylation.

Kingston Cian C Wallace Michael A MA Allentoff Alban J AJ deGruyter Justine N JN Chen Jason S JS Gong Sharon X SX Bonacorsi Samuel S Baran Phil S PS

Journal of the American Chemical Society 20190103 2

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 to afford a range of complex compounds with ample isotopic incorporations for drug metabolism and pharmacokinetic studies. The practicality and operational simplicity of the protocol were demonstrated by its use in an industrial carbon-14 radiolabeling setting. ...[more]

PMID: 30605319

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