@article{beb9690f798d42a8bc319187e66c59af,
title = "Thiourea-Catalyzed C−F Bond Activation: Amination of Benzylic Fluorides",
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.",
keywords = "C−F activation, benzyl amines, benzyl fluorides, organocatalysis, thiourea",
author = "Camille Houle and Savoie, {Paul R.} and Clotilde Davies and Damien Jardel and Champagne, {Pier Alexandre} and Brigitte Bibal and Paquin, {Jean Fran{\c c}ois}",
note = "Funding Information: We thank Aline Lacoudre (CESAMO, UMR 5255) for X‐ray crystallography of compounds (CCDC 1950215) and (CCDC 1950216). This work was supported by the Universit{\'e} de Bordeaux, the Centre National de la Recherche Scientifique (CNRS), the Natural Sciences and Engineering Research Council of Canada (NSERC), the FRQNT Network for Research on Protein Function, Engineering, and Applications (PROTEO), Universit{\'e} Laval and the New Jersey Institute of Technology (NJIT). Calculations were performed on the Kong cluster at NJIT. 2 c 2 h Funding Information: We thank Aline Lacoudre (CESAMO, UMR 5255) for X-ray crystallography of compounds 2 c (CCDC 1950215) and 2 h (CCDC 1950216). This work was supported by the Universit{\'e} de Bordeaux, the Centre National de la Recherche Scientifique (CNRS), the Natural Sciences and Engineering Research Council of Canada (NSERC), the FRQNT Network for Research on Protein Function, Engineering, and Applications (PROTEO), Universit{\'e} Laval and the New Jersey Institute of Technology (NJIT). Calculations were performed on the Kong cluster at NJIT. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",
year = "2020",
month = aug,
day = "17",
doi = "10.1002/chem.202001905",
language = "English (US)",
volume = "26",
pages = "10620--10625",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "46",
}