triethylamine; triphenylphosphine; palladium dichloride in water T=25°C; carbonylative Sonogashira coupling; 12 h;

1: carbon monoxide; Sb(o-tolyl)3 With [bis(acetoxy)iodo]benzene in dichloromethane T=20°C; 7 h; 2: 2-(4-methoxyphenyl)-1-trimethylsilyl-ethyne With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; copper(l) iodide in acetonitrile T=50°C; 5 h; Further stages.;

copper(l) iodide; triethylamine; triphenylphosphine T=50°C; 3 h; Inert atmosphere;

1: 4-ethynyl-1-methoxy-benzene With n-butyllithium in tetrahydrofuran; hexane T=0 - 20°C; 1.5 h; 2: 4-methyl-benzaldehyde in tetrahydrofuran; hexane T=0 - 20°C; 2 h; 3: With iodine; potassium carbonate; tert-butyl alcohol 2 h; Reflux;

1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine / tetrahydrofuran / 0.17 h / 25 °C / Inert atmosphere 1.2: 12 h / 25 °C / Inert atmosphere 2.1: methanol; potassium hydroxide / water / 12 h / 0 - 25 °C / Darkness; Inert atmosphere 3.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere View Scheme

1: methanol; potassium hydroxide / water / 12 h / 0 - 25 °C / Darkness; Inert atmosphere 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere View Scheme