Frustrated Lewis pair catalyzed hydrodehalogenation of benzyl-halides

Abstract

10 mol% B(2,6-C₆F₂H₃)₃ in the presence of excess tetramethylpiperidine (TMP) and H₂ (or D₂) is shown to catalyze the hydrogenative dehalogenation of benzyl-halides to give corresponding toluene derivatives. These reactions proceed via an initial FLP activation of H₂ yielding the ammonium hydridoborate [TMPH][HB(2,6-C₆F₂H₃)₃]. This species acts in analogy to a FLP to cooperatively activate C–X bond (X = Cl, Br, I) of benzyl-halides delivering hydride and generating the corresponding ammonium halide salts.