Triol-promoted activation of C–F bonds: Amination of benzylic fluorides under highly concentrated conditions mediated by 1,1,1-tris(hydroxymethyl)propane

• Pier Alexandre Champagne,
• Alexandre Saint-Martin,
• Mélina Drouin and
• Jean-François Paquin

Beilstein J. Org. Chem. 2013, 9, 2451–2456, doi:10.3762/bjoc.9.283

• 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. Keywords: C–F bond activation; highly concentrated

• fluorides, activated alkyl fluorides [22], using 1,1,1-tris(hydroxymethyl)propane as the triol. Furthermore, optimization of the reaction conditions have revealed that the reaction was best run under highly concentrated conditions [23]. Results and Discussion Our initial investigations were performed using

• conditions; nucleophilic substitution; hydrogen bond; organofluorine; triol; Introduction The discovery of mild methods for the activation of C–F bonds is of high importance both from a fundamental point of view as well as for potential practical applications [1]. Specifically for aliphatic monofluorides, a