palladium diacetate; triethylamine; biphenyl-2-yl-di-tert-butyl-phosphane in benzene T=100°C; 0.5 h; Inert atmosphere;

1: PCl5; SnCl4 / toluene 2: diethylene glycol / 220 - 230 °C View Scheme

1: 98 percent / hydrogen / 10percent palladium-charcoal / aq. ethanol 2: 86 percent / hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 20 h / Ambient temperature 3: 81 percent / H2O / 0 °C 4: 66 percent / 30percent hydrogen peroxide / acetic acid / 1.) 55-60 deg C, 2 h, 2.) 75-80 deg C, 15 h 5: 85 percent / 10percent aq. sodium hydroxide / 4 h / Heating 6: 1.) sodium nitrite, conc. HCl 2.) sodium azide / 1.) water 7: 2.4 percent / various solvent(s) / 4 h / 185 °C View Scheme

1: 75 percent / n-butyl-lithium / hexane; diethyl ether / 1.) -70 deg C, 2 h, 2.) room temperature, 2 h 2: 98 percent / hydrogen / 10percent palladium-charcoal / aq. ethanol 3: 86 percent / hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 20 h / Ambient temperature 4: 81 percent / H2O / 0 °C 5: 66 percent / 30percent hydrogen peroxide / acetic acid / 1.) 55-60 deg C, 2 h, 2.) 75-80 deg C, 15 h 6: 85 percent / 10percent aq. sodium hydroxide / 4 h / Heating 7: 1.) sodium nitrite, conc. HCl 2.) sodium azide / 1.) water 8: 2.4 percent / various solvent(s) / 4 h / 185 °C View Scheme

1.1: n-BuLi; N,N,N',N'-tetramethylethylenediamine / diethyl ether; hexane / -40 - 20 °C 1.2: 84 percent / diethyl ether; hexane / -70 - 20 °C 2.1: 49 percent / H2NNH2*H2O; KOH / bis-(2-methoxy-ethyl) ether; H2O / Heating View Scheme

palladium diacetate; triethylamine; biphenyl-2-yl-di-tert-butyl-phosphane in benzene T=100°C; 0.166667 h; in sealed-cap vial; Reactivity;

sodium hydride

palladium diacetate; triethylamine; biphenyl-2-yl-di-tert-butyl-phosphane in benzene T=100°C; 0.116667 h; in sealed-cap vial; Reactivity;

1: 81 percent / H2O / 0 °C 2: 66 percent / 30percent hydrogen peroxide / acetic acid / 1.) 55-60 deg C, 2 h, 2.) 75-80 deg C, 15 h 3: 85 percent / 10percent aq. sodium hydroxide / 4 h / Heating 4: 1.) sodium nitrite, conc. HCl 2.) sodium azide / 1.) water 5: 2.4 percent / various solvent(s) / 4 h / 185 °C View Scheme

1: 1.) sodium nitrite, conc. HCl 2.) sodium azide / 1.) water 2: 2.4 percent / various solvent(s) / 4 h / 185 °C View Scheme