silica-supported NaHSO4 in methanol T=20°C; 0.166667 h;

1.1: triphenylphosphine; copper(I) iodide; palladium(II) chloride / triethylamine / 0.5 h / 50 °C 1.2: 93 percent / 5 h / 85 °C 2.1: 75.4 percent / potassium hydroxide / toluene / 6 h / 100 °C View Scheme

1: p-iodo-[(tetrahydro-2H-pyran-2-yl)oxy]benzene With copper(l) iodide; triphenylphosphine; palladium dichloride; triethylamine T=50°C; 0.5 h; 2: 2-methyl-but-3-yn-2-ol T=85°C; 5 h;

pyridinium p-toluenesulfonate in dichloromethane T=20°C; Addition; 12 h;

1.1: triphenylphosphine; copper(I) iodide; palladium(II) chloride / triethylamine / 0.5 h / 50 °C 1.2: 93 percent / 5 h / 85 °C 2.1: 75.4 percent / potassium hydroxide / toluene / 6 h / 100 °C 3.1: 67 percent / pyridinium p-toluenesulfonate / ethanol / 1 h / 65 °C View Scheme

1.1: diisopropylamine; copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / 20 °C / Inert atmosphere 1.2: Cooling with ice 2.1: potassium fluoride; methanol / 4 h / 20 °C 3.1: diisopropylamine; copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / 2 h / 80 °C / Inert atmosphere 3.2: Cooling with ice 4.1: toluene-4-sulfonic acid / dichloromethane; methanol / 1 h / 30 °C View Scheme