Polyfluorinated Functionalized m‑Terphenyls. New Substituents and Ligands in Organometallic Synthesis

The synthesis and structural characterization of polyfluorinated arenes 2,4,6-(C6F5)3C6H2X and 2,6-(C6F5)2-4-BrC6H2X (X = NO2, Cl, Br) obtained in the Ullmann-type cross coupling reaction is reported. The nitro derivatives were reduced to the aromatic amines. The α-diimine [2,4,6-(C6F5)3C6H2NCMe]2 and 2,4,6-(C6F5)3C6H2I were obtained in condensation and Sandmeyer reactions, respectively, from the corresponding amine. The syntheses of 2,4,6-(C6F5)3C6H2NHC­(O)­H, 2,4,6-(C6F5)3C6H2NC, and 2,4,6-(C6F5)3C6H2Si­(X)­Me2 (X = H, F, Cl) are also described.