Synthesis of the bulky m-terphenyl phenol Ar*OH (Ar* =C6H3-2,6-Mes(2), Mes=2,4,6-trimethylphenyl) and the preparation and structural characterization of several of its metal complexes

The bulky in-terphenyl phenol Ar*OH 1 (Ar* = C6H3-2,6-Mes(2), Mes = 2,4,6-trimethylphenyl) was synthesized via the treatment of Ar*Li with nitrobenzene. The phenol 1 is prepared in modest to good yield using this method. Attempts were also made to prepare 1 through oxidation of the bulky boronic acid Ar*B(OH)(2) with Oxone (R), but this reaction was not suitable for preparative-scale reactions. Side products of the reaction between Ar*Li and nitrobenzene were identified as Ar*[N(O)Ph] and [C6H5N(O)](2) and were characterized by X-ray crystallography and EPR spectroscopy. A variety of main-group and transition-metal complexes of Ar*OH were prepared, namely Sn(OAr*)(2), Ge(OAr*)(2), [N(SiMe3)(2)]Ge(OAr*), [MeAl(OAr*)](2), and Ti(NMe2)(OAr*)(2). All compounds were characterized spectroscopically and most were studied by single-crystal X-ray diffraction as well.