copper(l) iodide; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride in triethylamine Sonogashira coupling reaction; 6 h; Heating;

copper(l) iodide; diethylamine; bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran T=20°C; 14 h;

piperidine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran T=20°C; Sonogashira coupling; 2 h;

1: 98 percent / periodic acid dihydrate; iodine / acetic acid; H2O; H2SO4 / 4 h / 60 - 65 °C 2: 53 percent / NaOH / triethylbenzylammonium chloride / dimethylsulfoxide; H2O / 6 h / 20 °C 3: 89 percent / triphenylphosphine; cuprous iodide / dichlorobis(triphenylphosphine)palladium(II) / triethylamine / 6 h / Heating View Scheme

1: 53 percent / NaOH / triethylbenzylammonium chloride / dimethylsulfoxide; H2O / 6 h / 20 °C 2: 89 percent / triphenylphosphine; cuprous iodide / dichlorobis(triphenylphosphine)palladium(II) / triethylamine / 6 h / Heating View Scheme