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- Title
Thiourea‐Catalyzed C−F Bond Activation: Amination of Benzylic Fluorides.
- Authors
Houle, Camille; Savoie, Paul R.; Davies, Clotilde; Jardel, Damien; Champagne, Pier Alexandre; Bibal, Brigitte; Paquin, Jean‐François
- 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.
- Subjects
THIOUREA; FLUORIDES; AMINATION; CATALYSTS; HYDROGEN bonding; ENERGY level transitions
- Publication
Chemistry - A European Journal, 2020, Vol 26, Issue 46, p10620
- ISSN
0947-6539
- Publication type
Academic Journal
- DOI
10.1002/chem.202001905