potassium carbonate in ethanol T=20°C; 20 h;

1: 85 percent / NaOH; water; tetra(n-butyl)ammonium bromide / toluene / 4 h / 60 °C 2: 87 percent / CuI; Pd(OAc)2PPh3 / tetrahydrofuran; various solvent(s) 3: 76 percent / KOH; water / tetrahydrofuran; methanol / 2 h / 20 °C View Scheme

1: 87 percent / CuI; Pd(OAc)2PPh3 / tetrahydrofuran; various solvent(s) 2: 76 percent / KOH; water / tetrahydrofuran; methanol / 2 h / 20 °C View Scheme

1: potassium hydroxide / dimethyl sulfoxide 2: palladium diacetate; copper(l) iodide; triphenylphosphine; diisopropylamine 3: potassium carbonate / methanol; diethyl ether View Scheme

1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine / 8 h / Inert atmosphere; Reflux 2: potassium carbonate / methanol / 3 h / 20 °C View Scheme

1: sulfuric acid; iodine; iodic acid / water; acetic acid / 1 h / 70 °C 2: tetrabutylammomium bromide; sodium hydroxide / water; toluene / 4 h / Reflux 3: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine / 8 h / Inert atmosphere; Reflux 4: potassium carbonate / methanol / 3 h / 20 °C View Scheme

1: tetrabutylammomium bromide; sodium hydroxide / water; toluene / 4 h / Reflux 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine / 8 h / Inert atmosphere; Reflux 3: potassium carbonate / methanol / 3 h / 20 °C View Scheme