CEISAM Conference: Frédéric LEROUX

As part of CEISAM’s lecture series, Frédéric Leroux from the University of Strasbourg will be presenting his work on Tuesday June 24 at 10:30 a.m. in the Marie Curie room.

Expanding the Toolbox of Fluorinated Motifs: Selective Strategies for
Fluoroalkylation and PFAS Alternatives

Frédéric R. Leroux,*
Université de Strasbourg, CNRS, UMR7042-LIMA, ECPM, 25 rue Becquerel, 67087 Strasbourg
*e-mail: frederic.leroux@unistra.fr

CV

Fluorinated groups are omnipresent in bioactive compounds due to their profound influence on key physicochemical properties. Strategically incorporating fluorinated chains allows fine-tuning of lipophilicity,
while metabolic stability and biological activity can be markedly enhanced through targeted fluorination.[1]
Our research has long focused on the synthesis of functionalized heteroarenes bearing emerging fluorinated substituents. One of our key approaches leverages fluoroalkylated amine reagents (FARs) as powerful and versatile tools for the regioselective introduction of fluorinated motifs.[2]
Building on this, we recently developed SO₂F₂-mediated fluoroalkylation strategies based on the activation
of fluorinated alcohols. [3] This approach enables selective N- and O-polyfluoroalkylation, unlocking valuable fluorinated building blocks with high relevance in life sciences. In parallel, we have pioneered direct deprotonative functionalization of the difluoromethyl group, providing streamlined access to
difluoromethylene-containing compounds with enhanced chemical properties.[4]
Beyond these synthetic advancements, we are also actively exploring sustainable alternatives to fluorinated
substituents that fall under PFAS regulations. Here, we will present our latest results in this emerging field,
highlighting promising strategies for next-generation fluorine chemistry.[5]

References

  • [1] S. Pazenok, D. Bernier, M. Donnard, G. Hanquet, A. Panossian, F. R. Leroux, Modern Fluorine-Containing Agrochemicals, in PATAI’S Chemistry of Functional Groups, 2022, pp. 1-77.
  • [2] a) E. Schmitt, A. Panossian, J. P. Vors, C. Funke, N. Lui, S. Pazenok, F. R. Leroux, Chem. Eur. J. 2016, 22, 11239-11244; b) E. Schmitt, B. Commare, A. Panossian, J. P. Vors, S. Pazenok, F. R. Leroux, Chem. Eur. J. 2018,24, 1311-1316.
  • [3] a) L. Santos, M. Donnard, A. Panossian, J. P. Vors, P. Jeschke, D. Bernier, S. Pazenok, F. R. Leroux, J. Org. Chem.2022, 87, 2012-2021; b) L. Santos, F. Audet, M. Donnard, A. Panossian, J. P. Vors, D. Bernier, S. Pazenok, F. R.Leroux, Chem. Eur. J. 2023, 29, e202300792; c) C. Plaçais, L. Wisson, I. Chataigner, M. Donnard, A. Panossian, J.-P. Vors, D. Bernier, S. Pazenok, F. R. Leroux, Org. Lett. 2024.
  • [4] a) L. Santos, A. Panossian, M. Donnard, J. P. Vors, S. Pazenok, D. Bernier, F. R. Leroux, Org. Lett. 2020, 22, 8741-8745; b) A. Messara, N. Vanthuyne, P. Diter, M. Elhabiri, A. Panossian, G. Hanquet, E. Magnier, F. R.Leroux, Eur.J. Org. Chem. 2021, 2021, 5019-5026; c) A. Messara, A. Panossian, K. Mikami, G. Hanquet, F. R. Leroux, Angew.Chem. Int. Ed. 2023, 62, e202215899.
  • [5] F. Audet, M. Donnard, A. Panossian, P. M. Holstein, D. Bernier, S. Pazenok, F. R. Leroux, Adv. Synth. Catal. 2024,366, 3466-3473.
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