dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; potassium phosphate; palladium diacetate in toluene T=100°C; 1.5 h;

1: 79 percent / hydrogen / vanadium-doped platinum on carbon / methanol / 15 h / 2585.74 Torr 2: 74 percent / K3PO4*H2O; 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl / Pd(OAc)2 / toluene / 1.5 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: 74 percent / K3PO4*H2O; 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl / Pd(OAc)2 / toluene / 1.5 h / 100 °C View Scheme

1: 98 percent / K2CO3 / dimethylformamide / 12 h / 75 °C 2: 80 percent / PPh3 / CH2Cl2 / 0 - 20 °C 3: 79 percent / hydrogen / vanadium-doped platinum on carbon / methanol / 15 h / 2585.74 Torr 4: 74 percent / K3PO4*H2O; 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl / Pd(OAc)2 / toluene / 1.5 h / 100 °C View Scheme

1: 80 percent / PPh3 / CH2Cl2 / 0 - 20 °C 2: 79 percent / hydrogen / vanadium-doped platinum on carbon / methanol / 15 h / 2585.74 Torr 3: 74 percent / K3PO4*H2O; 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl / Pd(OAc)2 / toluene / 1.5 h / 100 °C View Scheme