hydrogen in ethanol T=60°C; P=1500.15 Torr; 0.055 h; Inert atmosphereautoclave;

bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine T=20°C; Sonogashira coupling; 18 h; Inert atmosphere;

1: methoxybenzene With air; Bi(NO3)3·5H2O; iodine; bismuth(III) chloride in acetonitrile T=20°C; 6 h; 2: 1-ethynyl-3,5-dimethoxy benzene With piperidine; bis-triphenylphosphine-palladium(II) chloride in acetonitrile T=70°C; 3 h;

bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine T=20°C; Sonogashira Cross-Coupling; 18 h; Inert atmosphere;

1: hydrogenchloride; sodium nitrite / water / -10 - 5 °C / Cooling with acetone-dry ice 2: potassium iodide / water / 20 °C 3: copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / 20 °C / Inert atmosphere 4: potassium fluoride; methanol / 2 h / 20 °C 5: copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / 6 h / 20 °C / Inert atmosphere View Scheme

1: potassium iodide / water / 20 °C 2: copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / 20 °C / Inert atmosphere 3: potassium fluoride; methanol / 2 h / 20 °C 4: copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / 6 h / 20 °C / Inert atmosphere View Scheme

1: copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / 20 °C / Inert atmosphere 2: potassium fluoride; methanol / 2 h / 20 °C 3: copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / 6 h / 20 °C / Inert atmosphere View Scheme

1: potassium fluoride; methanol / 2 h / 20 °C 2: copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / 6 h / 20 °C / Inert atmosphere View Scheme