triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine in toluene T=100°C; 2 h;

triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine in toluene

1: 65.2 percent / conc. sulfuric acid, nitric acid (70percent) / CH2Cl2 / 2 h / 25 °C 2: 57.1 percent / triethylamine / dichlorobis(triphenylphosphine)palladium(II), triphenylphosphine, copper(I) iodide / toluene / 2 h / 100 °C View Scheme

1: 80.9 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 5 °C 2: 65.2 percent / conc. sulfuric acid, nitric acid (70percent) / CH2Cl2 / 2 h / 25 °C 3: 57.1 percent / triethylamine / dichlorobis(triphenylphosphine)palladium(II), triphenylphosphine, copper(I) iodide / toluene / 2 h / 100 °C View Scheme

1: trifluoromethanesulfonic anhydride, nitric acid / CH2Cl2 / 2.5 h / 0 - 25 °C 2: 68 percent / triethylamine / dichlorobis(triphenylphosphine)palladium(II), triphenylphosphine, copper(I) iodide / toluene View Scheme