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

Abstract

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 CCl 4 to 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.