(Trifluoromethylselenyl)methylchalcogenyl as Emerging Fluorinated Groups: Synthesis under Photoredox Catalysis and Determination of the Lipophilicity

    • Kevin Grollier[a]
    • Arnaud De Zordo-Banliat[b]
    • Flavien Bourdreux[b]
    • Bruce Pegot[b]
    • Guillaume Dagousset[b]
    • Emmanuel Magnier*[b]
    • Thierry Billard*[a, c]
    • [a]Institute of Chemistry and Biochemistry (ICBMS, UMR CNRS 5246) Univ Lyon, Universite Lyon 1, CNRS,CPE, INSA43 Bd du 11 novembre 1918, 69622 Villeurbanne (France)
    • [b]InstitutLavoisierdeVersailles (UMR CNRS 8180)Universit Paris-Saclay,UVSQ,CNRS78035 Versailles (France)
    • [c]CERMEP-In vivo imaging59 Bd Pinel, 69677 Lyon (France)

    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 physicochemical 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.

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