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

• 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; Medicin och hälsovetenskap; 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
• DOI: 10.1002/anie.202002341

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.