Ortho-bis(amino)arylnickel(II) halide complexes containing perfluoroalkyl chains as model catalyst precursors for use in fluorous biphase systems

A novel synthetic procedure is presented to modify 1,3-bis[(dimethylamino)methyl]benzene to accommodate perfluoro alkyl chains. These ligands are then converted into nickel- and platinum-chloride organometallic derivatives, which can serve as model compounds for use in homogeneous catalysis. A nickel complex is shown to be an active catalyst for the 1:1 addition of CCl4to methylmethacrylate (Kharasch addition reaction) in dichloromethane but lacks sufficient solubility for use under fluorous biphase conditions. The structure in the solid state of this fluorous Ni species, which is a rare example of a structurally characterised perfluoro organometallic compound, was elucidated by single crystal X-ray diffraction.