bis(benzonitrile)palladium(II) dichloride; trifuran-2-yl-phosphane in 1,4-dioxane T=100°C; 6 h;

1: 82 percent / triphenylphosphine, CCl4 / acetonitrile / 0.5 h 2: 75 percent / Pd(benzonitrile)2Cl2, tris(2-furyl)phosphine (TFP) / dioxane / 6 h / 100 °C View Scheme

1: 60 percent / DIBAL / diethyl ether; toluene / 0.5 h / 0 °C 2: 84 percent / 10percent aq. HCl / tetrahydrofuran / 0.5 h / Ambient temperature 3: 82 percent / triphenylphosphine, CCl4 / acetonitrile / 0.5 h 4: 75 percent / Pd(benzonitrile)2Cl2, tris(2-furyl)phosphine (TFP) / dioxane / 6 h / 100 °C View Scheme

1: 1.) tetrakis(triphenylphosphine)palladium(0), 2.) sodium carbonate / 1.) 1,2-dimethoxyethane, 20 min, 2.) 1,2-dimethoxyethane, water, reflux 2: 100 percent / hydrogen / Pd/C / ethanol / 1810.02 Torr View Scheme

1: 1.) NaNO2, HBr, 2.) CuBr 2: 1.) tetrakis(triphenylphosphine)palladium(0), 2.) sodium carbonate / 1.) 1,2-dimethoxyethane, 20 min, 2.) 1,2-dimethoxyethane, water, reflux 3: 100 percent / hydrogen / Pd/C / ethanol / 1810.02 Torr View Scheme

1.1: iodine; magnesium / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere 1.2: 0.5 h / 0 - 20 °C / Inert atmosphere 2.1: [bis(acetoxy)iodo]benzene; palladium diacetate / 7 h / 100 °C / Inert atmosphere 3.1: cesium fluoride / N,N-dimethyl-formamide / 2 h / 80 °C View Scheme

in acetone Ambient temperatureIrradiation;

Multistep reaction. Yields of byproduct given;