palladium 10 on activated carbon; hydrogen in ethanol T=30°C; P=3040.2 Torr; 21 h;

1: Pd0(tris(tert-butyl)phosphine)2; water; caesium carbonate / ethylene glycol dimethyl ether / 40.5 h / 80 °C 2: iodine cloride / dichloromethane / 2 h / 0 °C 3: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 21 h / 20 °C 4: palladium 10 on activated carbon; hydrogen / ethanol / 21 h / 30 °C / 3040.2 Torr View Scheme

1.1: sodium / toluene / 19 h / Reflux 2.1: n-butyllithium / diethyl ether; hexane / 20 h / 0 °C 2.2: 4 h / 0 - 20 °C 3.1: potassium fluoride; C56H51CuO2P3; 18-crown-6 ether / ethylene glycol diethyl ether / 22 h / 100 °C / Inert atmosphere 4.1: Pd0(tris(tert-butyl)phosphine)2; water; caesium carbonate / ethylene glycol dimethyl ether / 40.5 h / 80 °C 5.1: iodine cloride / dichloromethane / 2 h / 0 °C 6.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 21 h / 20 °C 7.1: palladium 10 on activated carbon; hydrogen / ethanol / 21 h / 30 °C / 3040.2 Torr View Scheme

1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 21 h / 20 °C 2: palladium 10 on activated carbon; hydrogen / ethanol / 21 h / 30 °C / 3040.2 Torr View Scheme

1.1: 2.5 h / 90 °C 2.1: sodium / toluene / 19 h / Reflux 3.1: n-butyllithium / diethyl ether; hexane / 20 h / 0 °C 3.2: 4 h / 0 - 20 °C 4.1: potassium fluoride; C56H51CuO2P3; 18-crown-6 ether / ethylene glycol diethyl ether / 22 h / 100 °C / Inert atmosphere 5.1: Pd0(tris(tert-butyl)phosphine)2; water; caesium carbonate / ethylene glycol dimethyl ether / 40.5 h / 80 °C 6.1: iodine cloride / dichloromethane / 2 h / 0 °C 7.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 21 h / 20 °C 8.1: palladium 10 on activated carbon; hydrogen / ethanol / 21 h / 30 °C / 3040.2 Torr View Scheme