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 and
agrochemical research. As a result, the design of straightforward
methodologies to access to these targets remains a challenge.1
Among the fluorinated motifs, our research group was interested
in the introduction of the CF2CO2Et residue by means of direct
C-H bond functionalization.2 Our process based on the use of
inexpensive copper catalyst and the commercially available
BrCF2CO2Et was applied to a broad range of substrates eg.
glycals,3a enamides,3b furans/benzofurans3c and electron-rich
aryls derivatives.3d Mechanistic studies pointed out a plausible
Cu(I)/Cu(III) catalytic cycle involved in these reactions pathways.
In a second 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, 4 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.5,6
