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John R Box1, Mickaël E Avanthay1, Darren L Poole2

  • 1School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS, UK.

Angewandte Chemie (International Ed. in English)
|January 27, 2023
PubMed
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Researchers developed a new electrochemical method for removing fluorine from trifluoromethyl (CF3) compounds. This process selectively converts CF3 groups into fluoromethyl moieties, enabling rapid diversification of chemical libraries.

Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Fluorine Chemistry

Background:

  • Trifluoromethyl (CF3) groups are important in medicinal chemistry and materials science.
  • Direct modification of CF3 groups can be challenging.
  • Existing methods for CF3 modification may lack selectivity or scalability.

Purpose of the Study:

  • To develop a general and selective procedure for the direct hydrodefluorination of ArCF3 compounds.
  • To enable the late-stage modification of CF3-containing molecules.
  • To facilitate the diversification of chemical libraries and lead compounds.

Main Methods:

  • Utilized electrochemistry with a tunable Ni cathode.
  • Developed a general procedure for mono- and di-hydrodefluorination.
Keywords:
DefluorinationElectrochemistryFluorineNickelReduction

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  • Operated the reaction under conditions achieving high selectivity and yields.

    • Main Results:

    • Achieved direct mono- and di-hydrodefluorination of ArCF3 compounds.
    • Demonstrated high selectivity and good to excellent yields.
    • Successfully scaled the reaction up to gram quantities.

    Conclusions:

    • The developed electrochemical method provides a versatile approach for modifying CF3 groups.
    • This technique allows for the late-stage peripheral editing of CF3 feedstocks.
    • The method aids in the rapid diversification of lead compounds and compound libraries.