Frustrated Lewis pair catalyzed hydrodehalogenation of benzyl-halides.
Tongtong WangMaotong XuAndrew R JuppShi-Ming ChenZheng-Wang QuStefan GrimmeDouglas W StephanPublished in: Chemical communications (Cambridge, England) (2022)
10 mol% B(2,6-C 6 F 2 H 3 ) 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-C 6 F 2 H 3 ) 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.