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

Authors

Camille Houle, Université Laval
Paul R. Savoie, Université Laval
Clotilde Davies, Université de Bordeaux
Damien Jardel, Université de Bordeaux
Pier Alexandre Champagne, New Jersey Institute of Technology
Brigitte Bibal, Université de Bordeaux
Jean François Paquin, Université Laval

Document Type

Article

Publication Date

8-17-2020

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.

Identifier

85088168149 (Scopus)

Publication Title

Chemistry A European Journal

External Full Text Location

https://doi.org/10.1002/chem.202001905

e-ISSN

15213765

ISSN

09476539

PubMed ID

32315102

First Page

10620

Last Page

10625

Issue

46

Volume

26

Grant

CCDC 1950216

Fund Ref

Université Laval

Recommended Citation

Houle, Camille; Savoie, Paul R.; Davies, Clotilde; Jardel, Damien; Champagne, Pier Alexandre; Bibal, Brigitte; and Paquin, Jean François, "Thiourea-Catalyzed C−F Bond Activation: Amination of Benzylic Fluorides" (2020). Faculty Publications. 5084.
https://digitalcommons.njit.edu/fac_pubs/5084