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Direct Carbon Isotope Exchange Through Decarboxylative Carboxylation

preprint
submitted on 09.11.2018 and posted on 09.11.2018 by Cian Kingston, Michael Wallace, Alban J. Allentoff, Justine deGruyter, Jason Chen, Sharon Gong, Samuel Bonacorsi, Jr., Phil Baran
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 was demonstrated by its use in an industrial carbon-14 radiolabeling setting.

Funding

Bristol-Myers Squibb and NSF GRFP (J. N. D.)

History

Email Address of Submitting Author

pbaran@scripps.edu

Institution

The Scripps Research Institute

Country

United States

ORCID For Submitting Author

0000-0001-9193-9053

Declaration of Conflict of Interest

No conflict of interest

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in Journal of the American Chemical Society

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