hydrogen iodide

AlCl3, aluminium chloride; sodium iodide in acetonitrile T=5°C; 1 h;

dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; palladium diacetate; caesium carbonate in 1,4-dioxane; water T=80°C; Suzuki Coupling; 3 h; Inert atmosphere;

sodium hydroxide in methanol; water Heating;

1: tetra-n-butylammonium tribromide / methanol; dichloromethane / 0.5 h / 20 °C 2: palladium diacetate; dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; caesium carbonate / 1,4-dioxane; water / 3 h / 80 °C / |Inert atmosphere View Scheme

1: thionyl chloride; 4-(N,N-dimethlyamino)pyridine / ethylene glycol dimethyl ether / 0 - 20 °C 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C 3: pyridine / 0 °C 4: tetrakis(triphenylphosphine) palladium(0); triethylamine / 1,4-dioxane / 2 h / 80 °C / |Inert atmosphere 5: palladium diacetate; dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; caesium carbonate / 1,4-dioxane; water / 3 h / 80 °C / |Inert atmosphere View Scheme

1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C 2: pyridine / 0 °C 3: tetrakis(triphenylphosphine) palladium(0); triethylamine / 1,4-dioxane / 2 h / 80 °C / |Inert atmosphere 4: palladium diacetate; dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; caesium carbonate / 1,4-dioxane; water / 3 h / 80 °C / |Inert atmosphere View Scheme

1: pyridine / 0 °C 2: tetrakis(triphenylphosphine) palladium(0); triethylamine / 1,4-dioxane / 2 h / 80 °C / |Inert atmosphere 3: palladium diacetate; dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; caesium carbonate / 1,4-dioxane; water / 3 h / 80 °C / |Inert atmosphere View Scheme

1: tetrakis(triphenylphosphine) palladium(0); triethylamine / 1,4-dioxane / 2 h / 80 °C / |Inert atmosphere 2: palladium diacetate; dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; caesium carbonate / 1,4-dioxane; water / 3 h / 80 °C / |Inert atmosphere View Scheme

1: sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; sodium chlorite / tert-butyl alcohol; acetonitrile; water / 0 - 20 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 20 °C 3: potassium carbonate; palladium diacetate / N,N-dimethyl acetamide / 0.75 h / 130 °C 4: AlCl3, aluminium chloride; sodium iodide / acetonitrile / 1 h / 5 °C View Scheme