1: hydrazine hydrate; potassium hydroxide / 1,2-bis-(2-hydroxyethoxy)-ethane / 210 °C / 760.05 Torr 2: copper(l) iodide; palladium(II) dichloride bis[bis(diphenylphosphine)ferrocene]; diisopropylamine; triphenylphosphine / 16 h / 90 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere View Scheme

1: AlCl3, aluminium chloride / 1 h / 50 °C 2: hydrazine hydrate; potassium hydroxide / 1,2-bis-(2-hydroxyethoxy)-ethane / 210 °C / 760.05 Torr 3: copper(l) iodide; palladium(II) dichloride bis[bis(diphenylphosphine)ferrocene]; diisopropylamine; triphenylphosphine / 16 h / 90 °C / Inert atmosphere 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere View Scheme

bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine T=100 - 120°C;

diisopropylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) in toluene T=20°C; Sonogashira coupling;