Results
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