Titre : Copper and Organofluorine Chemistry : an Interesting
Partnership
Endroit: Pavillon Roger-Gaudry, Salle G-815
Hôte : Prof. : Lebel Hélène
Résumé : Fluorinated molecules are of great interest in pharmaceutical and agrochemical research. As a result, the design of straightforward methodologies to access to these targets remains a challenge.1
Since 2011, our group focused on the development of Copper-based ransformation to access fluorinated molecules.
In a first part, our effort to develop a straightforward method to introduce the CF2PO(OEt)2 group will be disclosed. Indeed, due to the importance of this phosphate bioisoster,2 the need to develop efficient access is of prime importance in medicinal chemistry. The use of the CuCF2PO(OEt)2 reagent to introduce this motif will be depicted as well as the discovery of a Cu-salt controlled product distribution.3 A second part will describe our recent efforts to build up chiral fluorinated molecules using catalytic asymmetric process. 4 Finally, our first contribution in the field of copper photocatalyzed reactions will be disclosed.5
1 For selected reviews, see: (a) Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem. Int. Ed. 2013, 52, 8214.(b)
Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470. (c) Egami, H.; Shimizu, R.; Kawamura, S.; Sodeoka,
- Angew. Chem. Int. Ed. 2013, 52, 4000. (d) For a special issue on fluorine chemistry, see: Chem. Rev. 2015,
115, 563−1306.
2 Ivanova, M. V.; Bayle, A.; Besset, T.; Pannecoucke, X.; Poisson, T. Chem. Eur. J. 2016, 22, 10284.
3 (a) Ivanova, M. V.; Bayle, A.; Besset, T.; Poisson, T.; Pannecoucke, X. Angew. Chem. Int. Ed. 2015, 54, 13406.
(b) Ivanova, M. V.; Bayle, A.; Besset, T.; Pannecoucke, X.; Poisson, T. Angew. Chem. Int. Ed. 2016, 55, 14141.(c) Ivanova, M.; Besset, T.; Pannecoucke, X.; Poisson, T. Synthesis 2018, 50, 778. (d) Ivanova, M. V.; Bayle, A.;
Besset, T.; Pannecoucke, X.; Poisson, T. Chem. Eur. J. 2017, 23, 17318. (e) Ivanova, M. V.; Bayle, A.;
Pannecoucke, X.; Besset, T.; Poisson, T. Eur. J. Org. Chem. 2017, 2475.
4 (a) Pons, A.; Tognetti, V. T.; Joubert, L.; Poisson, T.; Pannecoucke, X.; Charette, A. B. C.; Jubault, P. ACSCatal. 2019, 9, 2594. (b) Huang, W.-S.; Delcourt, M.-L.; Pannecoucke, X.; Charette, A. B.; Poisson, T.; Jubault, P.
Org. Lett. 2019, 10.1021/acs.orglett.9b02792. (c) Poutrel, P.; Ivanova, M. V.; Pannecoucke, P.; Jubault, P.;
Poisson, T. Chem. Eur. J. 2019, 10.1002/chem.201904192.
5 Nitelet, A.; Thevenet, D.; Schiavi, B.; Hardouin, C.; Fournier, J.; Tamion, R.; Pannecoucke, X.; Jubault, P.;
Poisson, T. Chem. Eur. J. 2019, 25, 3262.
