Frustrated Lewis pair catalyzed hydrodehalogenation of benzyl-halides

10 mol% B(2,6-C6F2H3)(3) in the presence of excess tetramethylpiperidine (TMP) and H-2 (or D-2) is shown to catalyze the hydrogenative dehalogenation of benzyl-halides to give corresponding toluene derivatives. These reactions proceed via an initial FLP activation of H-2 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.

Automated summary

In the presence of 10 mol% B(2,6-C6F2H3)(3), excess tetramethylpiperidine (TMP) and H-2 (or D-2), catalytic hydrogenative dehalogenation of benzyl-halides to yield corresponding toluene derivatives is achieved. This reaction proceeds through the initial FLP activation of H-2 to form ammonium hydridoborate [TMPH][HB(2,6-C6F2H3)(3)], which then cooperatively activates the C-X bond (X = Cl, Br, I) of benzyl-halides to generate the corresponding ammonium halide salts.