hydrogen; palladium 10 on activated carbon in ethanol T=25 - 35°C; Product distribution / selectivity;

ammonia; sodium in tetrahydrofuran 0.166667 h;

1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 2: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme

sodium in tetrahydrofuran; ammonia T=-78°C; 0.75 h;

hydrogenchloride; polyphosphate ester; sodium carbonate in chloroform; water

1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 2: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 3: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme

1.1: sodium hydrogencarbonate; iodine / dichloromethane / 25 - 30 °C 2.1: dichloromethane / 1.5 h / 25 °C 3.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 3.2: 25 °C 4.1: potassium hydroxide; ethanol / 15 - 25 °C 5.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 5.2: 0.5 h / 25 °C 6.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 6.2: 10 - 15 °C / pH 8 7.1: hydrogen; acetic acid / palladium 10 on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 7.2: 10 °C / pH 7.5 - 8.5 View Scheme

1.1: dichloromethane / 1.5 h / 25 °C 2.1: copper(l) iodide; lithium chloride / N,N-dimethyl-formamide / 0.5 h / 25 °C 2.2: 25 °C 3.1: potassium hydroxide; ethanol / 15 - 25 °C 4.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 80 - 85 °C 4.2: 0.5 h / 25 °C 5.1: trifluoroacetic acid / ethanol / 25 °C / Reflux 5.2: 10 - 15 °C / pH 8 6.1: hydrogen; acetic acid / palladium 10 on activated carbon / 25 °C / 1448.05 - 2172.08 Torr 6.2: 10 °C / pH 7.5 - 8.5 View Scheme

1: 86 percent / t-BuOK / tetrahydrofuran / 4.5 h / -78 °C 2: 82 percent / triethylamine; methanesulfonyl chloride / CHCl3 / 25.25 h / 0 - 5 °C 3: 0.7 g / NaI*2H2O / acetone / 6 h / Heating 4: 64 percent / dimethylformamide; SOCl2 / benzene / 5 h / Heating 5: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C 6: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 7: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 8: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 9: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 10: 84 percent / KOH / methanol / 2 h / 20 °C 11: 83 percent / KOH / methanol / 8 h / Heating 12: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 13: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr 2: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 3: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 4: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme