title: Triol-promoted activation of C-F bonds: Amination of benzylic fluorides under highly concentrated conditions mediated by 1,1,1-tris(hydroxymethyl)propane.
abstract: Activation of the C-F bond of benzylic fluorides was achieved using 1,1,1-tris(hydroxymethyl)propane (2) as a hydrogen bond-donating agent. Investigations demonstrated that hydrogen bond-donating solvents are promoting the activation and hydrogen bond-accepting ones are hindering it. However, the reaction is best run under highly concentrated conditions, where solvents cannot interfere with the interaction between the organofluorine compound and the triol. Various benzylic fluorides react with secondary amines or anilines to form benzylic amines in good yields.
authors.affiliation: Canada Research Chair in Organic and Medicinal Chemistry, CCVC, PROTEO, Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC, Canada G1V 0A6.
authors.forename: Pier Alexandre
authors.initials: PA
authors.lastname: Champagne
authors.affiliation: Canada Research Chair in Organic and Medicinal Chemistry, CCVC, PROTEO, Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC, Canada G1V 0A6.
authors.forename: Alexandre
authors.initials: A
authors.lastname: Saint-Martin
authors.affiliation: Canada Research Chair in Organic and Medicinal Chemistry, CCVC, PROTEO, Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC, Canada G1V 0A6.
authors.forename: Mélina
authors.initials: M
authors.lastname: Drouin
authors.affiliation: Canada Research Chair in Organic and Medicinal Chemistry, CCVC, PROTEO, Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC, Canada G1V 0A6.
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Paquin
keywords: C–F bond activation; highly concentrated conditions; hydrogen bond; nucleophilic substitution; organofluorine; triol