Transition‐Metal‐Free Carbon Isotope Exchange of Phenyl Acetic Acids

A transition‐metal‐free carbon isotope exchange procedure on phenyl acetic acids is described. Utilizing the universal precursor CO2, this protocol allows the carbon isotope to be inserted into the carboxylic acid position, with no need of precursor synthesis. This procedure enabled the labeling of...

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Bibliographic Details
Published in:Angewandte Chemie International Edition Vol. 59; no. 32; pp. 13490 - 13495
Main Authors: Destro, Gianluca, Horkka, Kaisa, Loreau, Olivier, Buisson, David‐Alexandre, Kingston, Lee, Del Vecchio, Antonio, Schou, Magnus, Elmore, Charles S., Taran, Frédéric, Cantat, Thibault, Audisio, Davide
Format: Journal Article
Language:English
Published: WEINHEIM Wiley 03.08.2020
Wiley Subscription Services, Inc
Wiley-VCH Verlag
John Wiley and Sons Inc
Edition:International ed. in English
Subjects:
Acetic acid
Carbon
Carbon 13
Carbon 14
Carbon dioxide
Carbon isotopes
carbon-11
Carboxylic acids
Chemical Sciences
Chemistry
Chemistry, Multidisciplinary
Communication
Communications
Exchanging
isotope exchange
isotope labeling
Isotopes
Organic chemistry
Physical Sciences
Precursors
Radiochemistry
Science & Technology
carbon dioxide
CO2
LIGHT
isotope exchange
STEP
DISCOVERY
RADIOLABELED COMPOUNDS
METABOLISM
BONDS
DRUGS
CHEMISTRY
carbon-11
carbon-14
isotope labeling
CARBOXYLIC-ACIDS
Carbon-14
Carbon-11
Isotope exchange
Isotope labeling
Carbon dioxide
ISSN:1433-7851, 1521-3773, 1521-3773
Online Access:Get full text
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Summary:A transition‐metal‐free carbon isotope exchange procedure on phenyl acetic acids is described. Utilizing the universal precursor CO2, this protocol allows the carbon isotope to be inserted into the carboxylic acid position, with no need of precursor synthesis. This procedure enabled the labeling of 15 pharmaceuticals and was compatible with carbon isotopes [14C] and [13C]. A proof of concept with [11C] was also obtained with low molar activity valuable for distribution studies. Just labeled: Transition‐metal‐free carbon isotope exchange on phenyl acetic acids is described. Utilizing the universal precursor CO2, the carbon isotope can be inserted into the carboxylic acid position, with no need of precursor synthesis. This procedure enabled the labeling of 15 pharmaceuticals and was compatible with [14C] and [13C]. A proof of concept with [11C] was also obtained with low molar activity valuable for distribution studies.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202002341