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Fluorous phase, fluorinated alcohols

Fluoroalkyl alcohols TFE and HFIP possessed particular properties (acidity, polarity, high H-Bond donor, …), and allowed to perform clean and selective reactions without external promotor (Lewis acid, or Brönsted acid).

 Hexafluoroisopropanol (HFIP) and trifluoroethanol (TFE):

  • Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol (J. Org. Chem. 2018, 83, 930; highlighted in Synfacts 2018, 14(03), 0244).
  • Highly regioselective C–H amination between azodicarboxylate derivatives and a wide range of anilines. This approach provided a wide range of para-substituted anilines. The compatibility of a free amino group in this procedure is of high synthetic value (Eur. J. Org. Chem. 2017, 4753).
  • Effective and clean Friedel-Craft alkylation between β-nitroalkenes and arenes in HFIP. Further, this methodology can be applied to one-pot synthesis of biologically active tryptamine derivatives. (RSC Adv., 2018, 8, 10314)
  • Unprecedented 1,4-addition of poor nucleophiles onto sluggish (cumbersome) Michael acceptors by combining hexafluoroisopropanol and hyperbaric conditions (10−15 kbar). In collaboration with J. Maddaluno and J. Legros (Laboratoire COBRA UMR 6014, University of Rouen). (J. Org. Chem. 2015, 80, 10375).

 Fluorous phase (perfluoroethers) :

Perfluorinated solvents have the particularity of dissolving large quantities of gases such as oxygen and CO2. Although the exploitation of the solubility of oxygen in these solvents has been widely developed in the literature, the exploitation of the very high solubility of CO2 has not been studied at all.

Thus, we have shown that the opening reaction of epoxides into cyclic carbonates can be effective in perfluorinated solvents and in particular in the HydroFluoroEthers (HFE), the HFE-7500. The reactions can be carried out under mild conditions under a CO2 atmosphere at room temperature (Chem Commun. 2015, 51, 12736).