(Trifluoromethylselenyl)methylchalcogenyl as emerging fluorinated groups: synthesis under photoredox catalysis and determination of the lipophilicity - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2021

(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
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Dates et versions

hal-03407531 , version 1 (28-10-2021)

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Kevin Grollier, Arnaud de Zordo‐banliat, Flavien Bourdreux, Bruce Pegot, Guillaume Dagousset, et al.. (Trifluoromethylselenyl)methylchalcogenyl as emerging fluorinated groups: synthesis under photoredox catalysis and determination of the lipophilicity. Chemistry - A European Journal, 2021, 27 (19), pp.6028-6033. ⟨10.1002/chem.202100053⟩. ⟨hal-03407531⟩
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