Frustrated Lewis pair catalyzed hydrodehalogenation of benzyl-halides.

10 mol% B(2,6-CFH) in the presence of excess tetramethylpiperidine (TMP) and H (or D) is shown to catalyze the hydrogenative dehalogenation of benzyl-halides to give corresponding toluene derivatives. These reactions proceed an initial FLP activation of H yielding the ammonium hydridoborate [TMPH][HB(2,6-CFH)]. 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.