carbon monoxide; triphenylphosphine; palladium diacetate in acetonitrile T=70°C; P=4560 Torr; 12 h;

dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; potassium phosphate; palladium diacetate in toluene T=100°C; 2 h;

1: 85 percent / K2CO3 / dimethylformamide / 16 h / 45 °C 2: 79 percent / PPh3 / CH2Cl2 / 0 - 20 °C 3: 94 percent / hydrogen / vanadium-doped platinum on carbon / methanol / 3 h / 1292.87 Torr 4: 65 percent / K3PO4*H2O; 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl / Pd(OAc)2 / toluene / 2 h / 100 °C View Scheme

1.1: 73 percent / K2CO3 / dimethylformamide / 2 h / 50 °C 2.1: tetrahydrofuran; diethyl ether / 0.5 h / -5 °C 2.2: 84 percent / aq. I2 / tetrahydrofuran; diethyl ether / 2 h / 20 °C 3.1: TBAF; isopropyl acetate / tetrahydrofuran / 0.5 h / 20 °C 4.1: isopropyl acetate / tetrahydrofuran / 1 h / 20 °C 5.1: 7.09 g / DBU; isopropyl acetate / 1 h / 70 °C 6.1: 88 percent / PPh3; CO / Pd(OAc)2 / acetonitrile / 12 h / 70 °C / 4560 Torr View Scheme

1.1: tetrahydrofuran; diethyl ether / 0.5 h / -5 °C 1.2: 84 percent / aq. I2 / tetrahydrofuran; diethyl ether / 2 h / 20 °C 2.1: TBAF; isopropyl acetate / tetrahydrofuran / 0.5 h / 20 °C 3.1: isopropyl acetate / tetrahydrofuran / 1 h / 20 °C 4.1: 7.09 g / DBU; isopropyl acetate / 1 h / 70 °C 5.1: 88 percent / PPh3; CO / Pd(OAc)2 / acetonitrile / 12 h / 70 °C / 4560 Torr View Scheme

1: TBAF; isopropyl acetate / tetrahydrofuran / 0.5 h / 20 °C 2: isopropyl acetate / tetrahydrofuran / 1 h / 20 °C 3: 7.09 g / DBU; isopropyl acetate / 1 h / 70 °C 4: 88 percent / PPh3; CO / Pd(OAc)2 / acetonitrile / 12 h / 70 °C / 4560 Torr View Scheme

1: isopropyl acetate / tetrahydrofuran / 1 h / 20 °C 2: 7.09 g / DBU; isopropyl acetate / 1 h / 70 °C 3: 88 percent / PPh3; CO / Pd(OAc)2 / acetonitrile / 12 h / 70 °C / 4560 Torr View Scheme

1: 94 percent / hydrogen / vanadium-doped platinum on carbon / methanol / 3 h / 1292.87 Torr 2: 65 percent / K3PO4*H2O; 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl / Pd(OAc)2 / toluene / 2 h / 100 °C View Scheme

1.1: 95 percent / methanol 2.1: lithium diisopropylamide; triisopropyl borate / tetrahydrofuran / -78 - 0 °C 2.2: 95 percent / hydrochloric acid / tetrahydrofuran; H2O / 20 °C 3.1: 65 percent / K3PO4*H2O; 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl / Pd(OAc)2 / toluene / 2 h / 100 °C View Scheme

1: 85 percent / K2CO3 / dimethylformamide / 16 h / 45 °C 2: 79 percent / PPh3 / CH2Cl2 / 0 - 20 °C 3: 94 percent / hydrogen / vanadium-doped platinum on carbon / methanol / 3 h / 1292.87 Torr 4: 65 percent / K3PO4*H2O; 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl / Pd(OAc)2 / toluene / 2 h / 100 °C View Scheme