Davide Audisio, CEA, Université Paris Saclay, Département Médicaments et Technologies pour la Santé, SCBM, 91191 Gif-sur-Yvette, France

Late state carbon-14 labeling and isotope exchange

Carbon-14 radiolabeling is a unique tool that, in association with -counting and -imaging technologies, provides vital knowledge on the fate of synthetic organic molecules such as pharmaceuticals and agrochemicals.1 Traditional multistep synthesis and the associated costs have limited its utilization.2
Recently, we have explored late-stage carbon isotope labeling technologies starting from readily available 14C sources, such as [14C]CO2, [14C]CO and [14C]CN-.3 In this context, we have developed transitions metal catalyzed and photocatalyzed methodologies, to enable effective carbon-isotope exchange on carboxylic acids and nitrile containing molecules.4 These reactions expand the concept of late-stage carbon radiolabeling and provide a direct access to end-use labeled pharmaceuticals.

References

1.  E. M. Isin, C. S. Elmore, G. N. Nilsson, R. A. Thompson, L. Weidolf, Chem. Res. Toxicol. 2012, 25, 532.
2. R. Voges, J. R. Heys, T. Moenius, in “Preparation of Compounds Labeled with Tritium and Carbon-14”, John Wiley & Sons, Ltd, 2009, 393.
3. a) G. Destro, O. Loreau, E. Marcon, F. Taran, T. Cantat, D. Audisio J. Am. Chem. Soc. 2019, 141, 780.
   b) C. Kingston, M. A. Wallace, A. J. Allentoff, J. N. de Gruyter, J. S. Chen, S. X. Gong, S. Bonacorsi, Jr., P. S. Baran J. Am. Chem. Soc. 2019, 141, 774.
   c) G. Destro, K. Horkka, O. Loreau, D.-A. Buisson, L. Kingston, A. Del Vecchio, M. Schou, C. S. Elmore, F. Taran, T. Cantat, D. Audisio Angew. Chem. Int. Ed. 2020, 59, 13490.
4. M. Feng, J. De Oliveira, A. Sallustrau, G. Destro, P. Thuéry, S. Roy, T. Cantat, C. S. Elmore, J. Blankenstein, F. Taran, D. Audisio J. Am. Chem. Soc. 2021, 143, 5659.