Thiourea-Catalyzed C−F Bond Activation: Amination of Benzylic Fluorides

Camille Houle, Paul R. Savoie, Clotilde Davies, Damien Jardel, Pier Alexandre Champagne, Brigitte Bibal, Jean François Paquin

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

We describe the first thiourea-catalyzed C−F bond activation. The use of a thiourea catalyst and Ti(OiPr)4 as a fluoride scavenger allows the amination of benzylic fluorides to proceed in moderate to excellent yields. Preliminary results with S- and O-based nucleophiles are also presented. DFT calculations reveal the importance of hydrogen bonds between the catalyst and the fluorine atom of the substrate to lower the activation energy during the transition state.

Original languageEnglish (US)
Pages (from-to)10620-10625
Number of pages6
JournalChemistry - A European Journal
Volume26
Issue number46
DOIs
StatePublished - Aug 17 2020

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Keywords

  • C−F activation
  • benzyl amines
  • benzyl fluorides
  • organocatalysis
  • thiourea

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