(Trifluoromethylselenyl)methylchalcogenyl as emerging fluorinated groups: synthesis under photoredox catalysis and determination of the lipophilicity
Résumé
The synthesis of molecules bearing (trifluoromethylselenyl)methylchalcogenyl groups is described via an efficient two-step strategy based on a metal-free photoredox catalyzed decarboxylative trifluoromethylselenolation with good yields up to 88% which raised to 98% in flow chemistry conditions. The flow methods allowed also to scale up the reaction. The mechanism of this key reaction was studied. The physico-chemical characterization of these emerging groups was performed by determining their Hansch-Leo lipophilicity parameters with high values up to 2.24. This reaction was also extended to perfluoroalkylselenolation with yields up to 95%. Finally, this method was successfully applied to the functionalization of relevant bioactive molecules such as tocopherol or estrone derivatives.
Domaines
Chimie organique| Origine | Fichiers produits par l'(les) auteur(s) |
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