[Pd(1,3-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)imidazol-2-ylidene)(cinnamyl)Cl]; potassium 2-methyl-2-butoxide in 1,4-dioxane T=110°C; Buchwald-Hartwig Coupling; 12 h; Inert atmosphereSealed tube;

magnesium; ethylene dibromide 1.) THF, 30 min. reflux, 2.) r.t., 6 h; Yield given. Multistep reaction;

iodine; copper 1) 180-200 deg C, 2 h, 2) 225-230 deg C, 3 h;

copper(l) chloride in N,N-dimethyl-formamide RefluxInert atmosphere;

1: boron tribromide 2: Basic conditions 3: potassium phosphate; biphenyl-4-yl(di-tert-butylphosphine); palladium diacetate / tetrahydrofuran / 40 °C 4: 10 palladium on activated charcoal; hydrogen 5: pyridine 6: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diisopropylamine / N,N-dimethyl-formamide 7: methanol; potassium carbonate / tetrahydrofuran 8: platinum (II) chloride 9: boron tribromide 10: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione View Scheme

1.1: n-butyllithium / hexane; pentane / 20 °C 2.1: N,N-diethylphosphoramidous dichloride / toluene / 2 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 - 25 °C 3.2: 3 h / 0 - 25 °C View Scheme

1: boron tribromide 2: Basic conditions 3: potassium phosphate; biphenyl-4-yl(di-tert-butylphosphine); palladium diacetate / tetrahydrofuran / 40 °C 4: 10 palladium on activated charcoal; hydrogen 5: pyridine 6: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diisopropylamine / N,N-dimethyl-formamide 7: methanol; potassium carbonate / tetrahydrofuran 8: platinum (II) chloride 9: boron tribromide 10: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione 11: sodium tetrahydroborate / N,N-dimethyl-formamide View Scheme