palladium 10 on activated carbon; hydrogen in tetrahydrofuran T=40°C; P=3750.38 Torr; 24 h;

1: bromine; acetic acid / 0.33 h / 15 °C 2: dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; palladium diacetate; caesium carbonate / 1,4-dioxane; water / 2.5 h / 80 °C / Inert atmosphere 3: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 24 h / 40 °C / 3750.38 Torr View Scheme

1: 4-(N,N-dimethlyamino)pyridine; thionyl chloride / ethylene glycol dimethyl ether / 16 h / -15 - 20 °C 2: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 4 h / 0 - 20 °C 3: pyridine / 3.5 h / 0 °C 4: tetrakis(triphenylphosphine) palladium(0); triethylamine / 1,4-dioxane / 1.5 h / 80 °C 5: dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; palladium diacetate; caesium carbonate / 1,4-dioxane; water / 2.5 h / 80 °C / Inert atmosphere 6: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 24 h / 40 °C / 3750.38 Torr View Scheme

1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 4 h / 0 - 20 °C 2: pyridine / 3.5 h / 0 °C 3: tetrakis(triphenylphosphine) palladium(0); triethylamine / 1,4-dioxane / 1.5 h / 80 °C 4: dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; palladium diacetate; caesium carbonate / 1,4-dioxane; water / 2.5 h / 80 °C / Inert atmosphere 5: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 24 h / 40 °C / 3750.38 Torr View Scheme

1: pyridine / 3.5 h / 0 °C 2: tetrakis(triphenylphosphine) palladium(0); triethylamine / 1,4-dioxane / 1.5 h / 80 °C 3: dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; palladium diacetate; caesium carbonate / 1,4-dioxane; water / 2.5 h / 80 °C / Inert atmosphere 4: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 24 h / 40 °C / 3750.38 Torr View Scheme

1: tetrakis(triphenylphosphine) palladium(0); triethylamine / 1,4-dioxane / 1.5 h / 80 °C 2: dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; palladium diacetate; caesium carbonate / 1,4-dioxane; water / 2.5 h / 80 °C / Inert atmosphere 3: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 24 h / 40 °C / 3750.38 Torr View Scheme

1: dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; palladium diacetate; caesium carbonate / 1,4-dioxane; water / 2.5 h / 80 °C / Inert atmosphere 2: palladium 10 on activated carbon; hydrogen / tetrahydrofuran / 24 h / 40 °C / 3750.38 Torr View Scheme