Conférence de chimie avec le professeur Thomas Poisson de l’INSA de Rouen

Titre: ''Copper Mediated Difluoromethylation Reactions''

Endroit : Pavillon Roger-Gaudry, salle G-615

Heure : 11:00 AM

Hôte : Professeur André Charette

Résumé : 

Fluorinated molecules are of great interest in pharmaceutical andagrochemical research. As a result, the design of straightforwardmethodologies to access to these targets remains a challenge.1Among the fluorinated motifs, our research group was interestedin the introduction of the CF2CO2Et residue by means of directC-H bond functionalization.2 Our process based on the use ofinexpensive copper catalyst and the commercially availableBrCF2CO2Et was applied to a oad range of substrates eg.glycals,3a enamides,3b furans/benzofurans3c and electron-richaryls derivatives.3d Mechanistic studies pointed out a plausibleCu(I)/Cu(III) catalytic cycle involved in these reactions pathways.In a second part, our effort to develop a straightforward method tointroduce the CF2PO(OEt)2 group will be disclosed. Indeed, due tothe importance of this phosphate bioisoster, 4 the need to developefficient access is of prime importance in medicinal chemistry. Theuse of the CuCF2PO(OEt)2 reagent to introduce this motif will bedepicted as well as the discovery of a Cu-salt controlled productdistribution.5,6

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