1: copper(I) bromide; tetrakis(triphenylphosphine)palladium(0) / dioxane / 1.5 h / 90 °C 2: ammonium cerium(IV) nitrate; sulfuric acid / acetonitrile / 3 h / 20 °C View Scheme

1: 84 percent / copper(I) bromide; tetrakis(triphenylphosphine)palladium(0) / dioxane / 1.5 h / 90 °C 2: 52 percent / ammonium cerium(IV) nitrate; sulfuric acid / acetonitrile / 3 h / 20 °C 3: 73 percent / sodium azide; hydrochloric acid / methanol; H2O / 3.5 h / 20 °C / pH 4 View Scheme

1: copper(I) bromide; tetrakis(triphenylphosphine)palladium(0) / dioxane / 1.5 h / 90 °C 2: ammonium cerium(IV) nitrate; sulfuric acid / acetonitrile / 3 h / 20 °C 3: 64 percent / sodium azide; hydrochloric acid / methanol; H2O / 4 h / 20 °C / pH 4 View Scheme

1.1: copper(I) bromide; tetrakis(triphenylphosphine)palladium(0) / dioxane / 1.5 h / 90 °C 2.1: ammonium cerium(IV) nitrate; sulfuric acid / acetonitrile / 3 h / 20 °C 3.1: 64 percent / sodium azide; hydrochloric acid / methanol; H2O / 4 h / 20 °C / pH 4 4.1: 2 h / Heating 4.2: 76 percent / 4 h / Heating 5.1: 100 percent / diphenyl ether / 0.25 h / 200 - 220 °C View Scheme

Multi-step reaction with 2 steps 1: diphenylether / 1 h / 250 °C2: 2,6-dimethylpyridine; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 12 h / 20 °C  

Multi-step reaction with 6 steps 1: 87 percent / Pd(PPh3)4, LiCl / palladium / dioxane / 7 h / 100 °C2: 100 percent / trifluoroacetic acid / 1 h / 23 °C3: 100 percent / 0.5 h / 0 °C4: 85 percent / cerc ammonium nitrate / acetonitrile; H2O / 0.25 h / 23 °C5: 48 percent / tetrahydrofuran / 6 h / 23 °C6: 86 percent / HCl / tetrahydrofuran / 3 h / 70 - 80 °C  

Multi-step reaction with 5 steps 1: 87 percent / Pd(PPh3)4, LiCl / palladium / dioxane / 7 h / 100 °C2: 100 percent / trifluoroacetic acid / 1 h / 23 °C3: 100 percent / 0.5 h / 0 °C4: 85 percent / cerc ammonium nitrate / acetonitrile; H2O / 0.25 h / 23 °C5: 48 percent / tetrahydrofuran / 6 h / 23 °C