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

Camille HoulePaul R SavoieClotilde DaviesDamien JardelPier Alexandre ChampagneBrigitte BibalJean-François Paquin

Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2020)

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.

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