1: 84 percent / zinc dust, acetic acid / tetrahydrofuran / 0.25 h / 45 °C 2: 81 percent / cerium(IV) ammonium nitrate, HNO3 / ethanol / 0.25 h / -42 °C 3: 80 percent / L-selectride / tetrahydrofuran / 2 h / -78 °C 4: pyridine / 1 h / 0 °C 5: 100 percent / sodium azide, ammonium chloride / dimethylformamide / 16 h / 22 °C 6: 4 N HCl / dioxane / 96 h / 22 °C 7: 554 mg / sodium acetate / 6.5 h / 50 °C 8: 59 percent / SnCl4 / CH2Cl2; acetonitrile / 16 h / 22 °C 9: 88 percent / potassium carbonate, acetic acid / methanol / 0.75 h / 22 °C 10: 91 percent / H2 / palladium hydroxide on carbon / methanol / 44 h / 3102.9 Torr 11: trifluoroacetic acid/water (9/1) / 1 h / 22 °C 12: 49 percent / liquid ammonia, sodium / -78 °C View Scheme

1: 4 N HCl / dioxane / 96 h / 22 °C 2: 554 mg / sodium acetate / 6.5 h / 50 °C 3: 59 percent / SnCl4 / CH2Cl2; acetonitrile / 16 h / 22 °C 4: 88 percent / potassium carbonate, acetic acid / methanol / 0.75 h / 22 °C 5: 91 percent / H2 / palladium hydroxide on carbon / methanol / 44 h / 3102.9 Torr 6: trifluoroacetic acid/water (9/1) / 1 h / 22 °C 7: 49 percent / liquid ammonia, sodium / -78 °C View Scheme

1: 96 percent / dicyclohexylcarbodiimde, copper(I) chloride / acetonitrile / 16 h / 35 °C 2: 84 percent / zinc dust, acetic acid / tetrahydrofuran / 0.25 h / 45 °C 3: 81 percent / cerium(IV) ammonium nitrate, HNO3 / ethanol / 0.25 h / -42 °C 4: 80 percent / L-selectride / tetrahydrofuran / 2 h / -78 °C 5: pyridine / 1 h / 0 °C 6: 100 percent / sodium azide, ammonium chloride / dimethylformamide / 16 h / 22 °C 7: 4 N HCl / dioxane / 96 h / 22 °C 8: 554 mg / sodium acetate / 6.5 h / 50 °C 9: 59 percent / SnCl4 / CH2Cl2; acetonitrile / 16 h / 22 °C 10: 88 percent / potassium carbonate, acetic acid / methanol / 0.75 h / 22 °C 11: 91 percent / H2 / palladium hydroxide on carbon / methanol / 44 h / 3102.9 Torr 12: trifluoroacetic acid/water (9/1) / 1 h / 22 °C 13: 49 percent / liquid ammonia, sodium / -78 °C View Scheme

1: 91 percent / H2 / palladium hydroxide on carbon / methanol / 44 h / 3102.9 Torr 2: trifluoroacetic acid/water (9/1) / 1 h / 22 °C 3: 49 percent / liquid ammonia, sodium / -78 °C View Scheme

1: 88 percent / potassium carbonate, acetic acid / methanol / 0.75 h / 22 °C 2: 91 percent / H2 / palladium hydroxide on carbon / methanol / 44 h / 3102.9 Torr 3: trifluoroacetic acid/water (9/1) / 1 h / 22 °C 4: 49 percent / liquid ammonia, sodium / -78 °C View Scheme

1: 100 percent / sodium azide, ammonium chloride / dimethylformamide / 16 h / 22 °C 2: 4 N HCl / dioxane / 96 h / 22 °C 3: 554 mg / sodium acetate / 6.5 h / 50 °C 4: 59 percent / SnCl4 / CH2Cl2; acetonitrile / 16 h / 22 °C 5: 88 percent / potassium carbonate, acetic acid / methanol / 0.75 h / 22 °C 6: 91 percent / H2 / palladium hydroxide on carbon / methanol / 44 h / 3102.9 Torr 7: trifluoroacetic acid/water (9/1) / 1 h / 22 °C 8: 49 percent / liquid ammonia, sodium / -78 °C View Scheme

1: 59 percent / SnCl4 / CH2Cl2; acetonitrile / 16 h / 22 °C 2: 88 percent / potassium carbonate, acetic acid / methanol / 0.75 h / 22 °C 3: 91 percent / H2 / palladium hydroxide on carbon / methanol / 44 h / 3102.9 Torr 4: trifluoroacetic acid/water (9/1) / 1 h / 22 °C 5: 49 percent / liquid ammonia, sodium / -78 °C View Scheme

1: 1) iodobenzene bis(trifluoroacetate), 2) pyridine / 1) DMF, room temp., 30 min, 2) room temp., 2 h 2: triethylamine / dimethylformamide / 2 h / Ambient temperature View Scheme

1: trifluoroacetic acid/water (9/1) / 1 h / 22 °C 2: 49 percent / liquid ammonia, sodium / -78 °C View Scheme

Yield given. Multistep reaction;