sodium carbonate; tetrakis(triphenylphosphine) palladium(0) in water; toluene 8 h; RefluxInert atmosphere;

1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate in 1-methyl-pyrrolidin-2-one T=100°C; 12 h;

1: With AlCl3, aluminium chloride; lithium aluminium tetrahydride in tetrahydrofuran T=-78 - 20°C; Cooling with acetone-dry iceInert atmosphereReflux; 2: With palladium on carbon in anhydrous xylene 216 h; Inert atmosphereReflux;

potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) in toluene 2 h; Heating / reflux;

1: 70 percent / NaHCO3 / toluene / 36 h / 145 °C 2: 91 percent / conc. HCl / methanol / 15 h / Heating 3: 81 percent / MCPBA / CHCl3 / Ambient temperature 4: 1.) CuI / 1.) Et2O, -10 deg C, 20 min, 2.) Et2O, 0 deg C, 1 h 5: 68 percent / o-chloranil / toluene / Heating View Scheme

1: 81 percent / MCPBA / CHCl3 / Ambient temperature 2: 1.) CuI / 1.) Et2O, -10 deg C, 20 min, 2.) Et2O, 0 deg C, 1 h 3: 68 percent / o-chloranil / toluene / Heating View Scheme

1: 1.) CuI / 1.) Et2O, -10 deg C, 20 min, 2.) Et2O, 0 deg C, 1 h 2: 68 percent / o-chloranil / toluene / Heating View Scheme

1: 91 percent / conc. HCl / methanol / 15 h / Heating 2: 81 percent / MCPBA / CHCl3 / Ambient temperature 3: 1.) CuI / 1.) Et2O, -10 deg C, 20 min, 2.) Et2O, 0 deg C, 1 h 4: 68 percent / o-chloranil / toluene / Heating View Scheme

1.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / ethylene glycol dimethyl ether; water / 48 h / 80 °C 2.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / tetrahydrofuran / -78 - 20 °C / Cooling with acetone-dry ice; Inert atmosphere; Reflux 2.2: 216 h / Inert atmosphere; Reflux View Scheme

1.1: hydrogenchloride; sodium nitrite / water / 1.33 h / 5 °C / Cooling with ice 1.2: 0.5 h / 20 °C 2.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / ethylene glycol dimethyl ether; water / 48 h / 80 °C 3.1: lithium aluminium tetrahydride; AlCl3, aluminium chloride / tetrahydrofuran / -78 - 20 °C / Cooling with acetone-dry ice; Inert atmosphere; Reflux 3.2: 216 h / Inert atmosphere; Reflux View Scheme