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

The synthesis and structural characterization of polyfluorinated arenes 2,4,6-(C 6 F 5 ) 3 C 6 H 2 X and 2,6-(C 6 F 5 ) 2 -4-BrC 6 H 2 X (X = NO 2, 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-(C 6 F 5 ) 3 C 6 H 2 NCMe] 2 and 2,4,6-(C 6 F 5 ) 3 C 6 H 2 I were obtained in condensation and Sandmeyer reactions, respectively, from the corresponding amine. The syntheses of 2,4,6-(C 6 F 5 ) 3 C 6 H 2 NHC(O)H, 2,4,6-(C 6 F 5 ) 3 C 6 H 2 NC, and 2,4,6-(C 6 F 5 ) 3 C 6 H 2 Si(X)Me 2 (X = H, F, Cl) are also described.