zinc(II) chloride in 1,4-dioxane T=100°C; 1.5 h;

1: 88 percent / K2CO3 / dimethylsulfoxide 2: 95 percent / Pd(PPh3)2Cl2; CuI; triethylamine / tetrahydrofuran / 1.5 h / 80 °C View Scheme

triphenylphosphine in tetrahydrofuran T=70°C; Negishi Coupling; 24 h; Inert atmosphereGreen chemistry; Catalytic behavior;

1: sulfuric acid / methanol 2: triethylamine / tetrahydrofuran; cyclohexane; ethyl acetate View Scheme

bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine 1.) THF, 25 deg C, 20 min, 2.) THF, 25 deg C, 16 h; Yield givenMultistep reaction. Yields of byproduct given;

1: 81 percent / sodium carbonate / methanol / 3 h / 20 °C 2: 91 percent / Pd(PPh3)2Cl2; CuI; triethylamine / 2 h / 20 °C 3: 0.48 g / NaOH / methanol / 24 h / Heating View Scheme

1.1: sodium hydroxide / ethanol / 18 h / 20 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 20 °C 2.2: 18 h / 20 °C 3.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 3 h / 20 °C / |Inert atmosphere 4.1: tetrahydrofuran; acetic acid / 0.08 h / 20 °C / |Inert atmosphere 4.2: 4 h / 20 °C / |Inert atmosphere 5.1: hydroxylamine; potassium cyanide / tetrahydrofuran; methanol; water / 18 h / 20 °C View Scheme

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere 2.1: 1H-imidazole / tetrahydrofuran / 15 h / 0 - 20 °C / |Inert atmosphere 3.1: potassium carbonate; methanol / 2 h / 20 °C / |Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / |Inert atmosphere 4.2: 0.5 h / 20 °C / |Inert atmosphere 5.1: hydrogen; palladium 10 on activated carbon / ethyl acetate / 15001.5 Torr 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C / |Inert atmosphere View Scheme