1: 94 percent / iodine; periodic acid / ethanol / 1 h / 40 °C 2: 82 percent / potassium carbonate / dimethylformamide / 1 h / 70 °C 3: potassium hydroxide / ethanol / 1 h / Heating 4: 5.48 g / aq. HCl / ethanol; CHCl3 / 1 h / 40 °C 5: 88 percent / potassium carbonate / dimethylformamide / 0.5 h / 60 - 70 °C 6: [hydroxy(tosyloxy)iodo]benzene / CHCl3 / 24 h / 20 °C 7: 3.82 g / aq. sodium hydroxide; methanol / CHCl3 / 5 h / 25 °C 8: 91 percent / triethylamine; PPh3; CuI / PdCl2 / dimethylformamide / 2 h / 80 °C 9: 88 percent / hydrogen / palladium on carbon / methanol; dioxane 10: 85 percent / potassium carbonate / acetone / 0.42 h / 45 °C 11: 84 percent / potassium carbonate / acetone / 2 h / Heating 12: 57 percent / p-TsOH hydrate; acetic acid / toluene / 1.5 h / Heating 13: 91 percent / BCl3 / CH2Cl2 / 2.5 h / 20 - 25 °C 14: 72 percent / aq. sodium hydroxide / methanol; dioxane / 0.33 h / 25 °C View Scheme

1: 95 percent / hydrogen / palladium on carbon / methanol; ethyl acetate / 20 °C 2: 94 percent / iodine; periodic acid / ethanol / 1 h / 40 °C 3: 82 percent / potassium carbonate / dimethylformamide / 1 h / 70 °C 4: potassium hydroxide / ethanol / 1 h / Heating 5: 5.48 g / aq. HCl / ethanol; CHCl3 / 1 h / 40 °C 6: 88 percent / potassium carbonate / dimethylformamide / 0.5 h / 60 - 70 °C 7: [hydroxy(tosyloxy)iodo]benzene / CHCl3 / 24 h / 20 °C 8: 3.82 g / aq. sodium hydroxide; methanol / CHCl3 / 5 h / 25 °C 9: 91 percent / triethylamine; PPh3; CuI / PdCl2 / dimethylformamide / 2 h / 80 °C 10: 88 percent / hydrogen / palladium on carbon / methanol; dioxane 11: 85 percent / potassium carbonate / acetone / 0.42 h / 45 °C 12: 84 percent / potassium carbonate / acetone / 2 h / Heating 13: 57 percent / p-TsOH hydrate; acetic acid / toluene / 1.5 h / Heating 14: 91 percent / BCl3 / CH2Cl2 / 2.5 h / 20 - 25 °C 15: 72 percent / aq. sodium hydroxide / methanol; dioxane / 0.33 h / 25 °C View Scheme

1: 95 percent / H2 / Pd/C / methanol; ethyl acetate / 20 °C 2: 96 percent / I2; periodic acid / ethanol; H2O / 0.03 h / 45 °C / microwave irradiation 3: 82 percent / K2CO3 / dimethylformamide / 1 h / 70 °C 4: KOH / ethanol / 0.1 h / 88 °C / microwave irradiation 5: 5.99 g / aq. HCl / methanol; CHCl3 / 1 h / 40 °C 6: 91 percent / pyridine / 0.08 h / 125 °C / microwave irradiation 7: [hydroxy(tosyloxy)iodo]benzene / CHCl3 / 0.2 h / 60 °C / microwave irradiation 8: 3.51 g / aq. NaOH / methanol; CHCl3 / 0.08 h / 50 °C / microwave irradiation 9: 78 percent / Et3N; PdCl2; PPh3 / CuI / dimethylformamide / 0.13 h / 80 °C / microwave irradiation 10: 88 percent / H2 / Pd/C / methanol; dioxane / 1 h / 20 °C 11: 85 percent / K2CO3 / acetone / 0.42 h / 45 °C 12: 89 percent / K2CO3 / acetone / 0.13 h / microwave irradiation 13: 74 percent / TsOH*H2O; acetic acid / toluene / 0.25 h / 117 °C / microwave irradiation 14: 91 percent / BCl3 / CH2Cl2 / 2.5 h / cooling 15: 72 percent / aq. NaOH / methanol; dioxane / 0.33 h / 25 °C View Scheme

1: 91 percent / pyridine / 0.08 h / 125 °C / microwave irradiation 2: [hydroxy(tosyloxy)iodo]benzene / CHCl3 / 0.2 h / 60 °C / microwave irradiation 3: 3.51 g / aq. NaOH / methanol; CHCl3 / 0.08 h / 50 °C / microwave irradiation 4: 78 percent / Et3N; PdCl2; PPh3 / CuI / dimethylformamide / 0.13 h / 80 °C / microwave irradiation 5: 88 percent / H2 / Pd/C / methanol; dioxane / 1 h / 20 °C 6: 85 percent / K2CO3 / acetone / 0.42 h / 45 °C 7: 89 percent / K2CO3 / acetone / 0.13 h / microwave irradiation 8: 74 percent / TsOH*H2O; acetic acid / toluene / 0.25 h / 117 °C / microwave irradiation 9: 91 percent / BCl3 / CH2Cl2 / 2.5 h / cooling 10: 72 percent / aq. NaOH / methanol; dioxane / 0.33 h / 25 °C View Scheme

Sophora flavescens microsomes; magnesium chloride in ethanol; water T=25°C; Substitution; pH=9; Enzymatic reaction;

1: [hydroxy(tosyloxy)iodo]benzene / CHCl3 / 24 h / 20 °C 2: 3.82 g / aq. sodium hydroxide; methanol / CHCl3 / 5 h / 25 °C 3: 91 percent / triethylamine; PPh3; CuI / PdCl2 / dimethylformamide / 2 h / 80 °C 4: 88 percent / hydrogen / palladium on carbon / methanol; dioxane 5: 85 percent / potassium carbonate / acetone / 0.42 h / 45 °C 6: 84 percent / potassium carbonate / acetone / 2 h / Heating 7: 57 percent / p-TsOH hydrate; acetic acid / toluene / 1.5 h / Heating 8: 91 percent / BCl3 / CH2Cl2 / 2.5 h / 20 - 25 °C 9: 72 percent / aq. sodium hydroxide / methanol; dioxane / 0.33 h / 25 °C View Scheme

1: 88 percent / potassium carbonate / dimethylformamide / 0.5 h / 60 - 70 °C 2: [hydroxy(tosyloxy)iodo]benzene / CHCl3 / 24 h / 20 °C 3: 3.82 g / aq. sodium hydroxide; methanol / CHCl3 / 5 h / 25 °C 4: 91 percent / triethylamine; PPh3; CuI / PdCl2 / dimethylformamide / 2 h / 80 °C 5: 88 percent / hydrogen / palladium on carbon / methanol; dioxane 6: 85 percent / potassium carbonate / acetone / 0.42 h / 45 °C 7: 84 percent / potassium carbonate / acetone / 2 h / Heating 8: 57 percent / p-TsOH hydrate; acetic acid / toluene / 1.5 h / Heating 9: 91 percent / BCl3 / CH2Cl2 / 2.5 h / 20 - 25 °C 10: 72 percent / aq. sodium hydroxide / methanol; dioxane / 0.33 h / 25 °C View Scheme

1: 85 percent / potassium carbonate / acetone / 0.42 h / 45 °C 2: 84 percent / potassium carbonate / acetone / 2 h / Heating 3: 57 percent / p-TsOH hydrate; acetic acid / toluene / 1.5 h / Heating 4: 91 percent / BCl3 / CH2Cl2 / 2.5 h / 20 - 25 °C 5: 72 percent / aq. sodium hydroxide / methanol; dioxane / 0.33 h / 25 °C View Scheme

1: 5.48 g / aq. HCl / ethanol; CHCl3 / 1 h / 40 °C 2: 88 percent / potassium carbonate / dimethylformamide / 0.5 h / 60 - 70 °C 3: [hydroxy(tosyloxy)iodo]benzene / CHCl3 / 24 h / 20 °C 4: 3.82 g / aq. sodium hydroxide; methanol / CHCl3 / 5 h / 25 °C 5: 91 percent / triethylamine; PPh3; CuI / PdCl2 / dimethylformamide / 2 h / 80 °C 6: 88 percent / hydrogen / palladium on carbon / methanol; dioxane 7: 85 percent / potassium carbonate / acetone / 0.42 h / 45 °C 8: 84 percent / potassium carbonate / acetone / 2 h / Heating 9: 57 percent / p-TsOH hydrate; acetic acid / toluene / 1.5 h / Heating 10: 91 percent / BCl3 / CH2Cl2 / 2.5 h / 20 - 25 °C 11: 72 percent / aq. sodium hydroxide / methanol; dioxane / 0.33 h / 25 °C View Scheme

1: 84 percent / potassium carbonate / acetone / 2 h / Heating 2: 57 percent / p-TsOH hydrate; acetic acid / toluene / 1.5 h / Heating 3: 91 percent / BCl3 / CH2Cl2 / 2.5 h / 20 - 25 °C 4: 72 percent / aq. sodium hydroxide / methanol; dioxane / 0.33 h / 25 °C View Scheme