sodium hydroxide; Ra-Ni 0.166667 h; Heating;

1: 80 percent / cuprous iodide / dimethylformamide / 1 h / 100 °C 2: 95 percent / sulfuric acid / 0.08 h 3: 86 percent / triphenyl phosphine, n-tributyl amine, water / PdCl2(PPh3)2 / 18 h / 110 °C / 7600 Torr 4: 95 percent / 10percent NaOH / 1 h / Heating 5: 80 percent / HCl / 4 h 6: 1.) 6N HCl, sodium nitrite / 1.) -10 deg C; 2.) dioxane, water, 80 deg C, 10 min 7: 85 percent / MnO2 / CH2Cl2 / Ambient temperature; 2-3 h 8: 1.) NaBH4; 2.) MnO2 / 1.) PdCl2(PPh)2 / 1.) methanol, 15 min; 2.) DCM, 30 min View Scheme

1: 1.) 6N HCl, sodium nitrite / 1.) -10 deg C; 2.) dioxane, water, 80 deg C, 10 min 2: 85 percent / MnO2 / CH2Cl2 / Ambient temperature; 2-3 h 3: 1.) NaBH4; 2.) MnO2 / 1.) PdCl2(PPh)2 / 1.) methanol, 15 min; 2.) DCM, 30 min View Scheme

1: 90 percent / NaBH4 / methanol / 3 h / Heating 2: 78 percent / ceric ammonium nitrate / H2O; acetonitrile / 3-4 h 3: 1.) 6N HCl, sodium nitrite / 1.) -10 deg C; 2.) dioxane, water, 80 deg C, 10 min 4: 85 percent / MnO2 / CH2Cl2 / Ambient temperature; 2-3 h 5: 1.) NaBH4; 2.) MnO2 / 1.) PdCl2(PPh)2 / 1.) methanol, 15 min; 2.) DCM, 30 min View Scheme

1: 78 percent / ceric ammonium nitrate / H2O; acetonitrile / 3-4 h 2: 1.) 6N HCl, sodium nitrite / 1.) -10 deg C; 2.) dioxane, water, 80 deg C, 10 min 3: 85 percent / MnO2 / CH2Cl2 / Ambient temperature; 2-3 h 4: 1.) NaBH4; 2.) MnO2 / 1.) PdCl2(PPh)2 / 1.) methanol, 15 min; 2.) DCM, 30 min View Scheme

1: 80 percent / HCl / 4 h 2: 1.) 6N HCl, sodium nitrite / 1.) -10 deg C; 2.) dioxane, water, 80 deg C, 10 min 3: 85 percent / MnO2 / CH2Cl2 / Ambient temperature; 2-3 h 4: 1.) NaBH4; 2.) MnO2 / 1.) PdCl2(PPh)2 / 1.) methanol, 15 min; 2.) DCM, 30 min View Scheme

1: 80 percent / bromine-dioxane complex / dioxane 2: 80 percent / cuprous iodide / dimethylformamide / 1 h / 100 °C 3: 95 percent / sulfuric acid / 0.08 h 4: 86 percent / triphenyl phosphine, n-tributyl amine, water / PdCl2(PPh3)2 / 18 h / 110 °C / 7600 Torr 5: 95 percent / 10percent NaOH / 1 h / Heating 6: 80 percent / HCl / 4 h 7: 1.) 6N HCl, sodium nitrite / 1.) -10 deg C; 2.) dioxane, water, 80 deg C, 10 min 8: 85 percent / MnO2 / CH2Cl2 / Ambient temperature; 2-3 h 9: 1.) NaBH4; 2.) MnO2 / 1.) PdCl2(PPh)2 / 1.) methanol, 15 min; 2.) DCM, 30 min View Scheme

1: 86 percent / triphenyl phosphine, n-tributyl amine, water / PdCl2(PPh3)2 / 18 h / 110 °C / 7600 Torr 2: 95 percent / 10percent NaOH / 1 h / Heating 3: 80 percent / HCl / 4 h 4: 1.) 6N HCl, sodium nitrite / 1.) -10 deg C; 2.) dioxane, water, 80 deg C, 10 min 5: 85 percent / MnO2 / CH2Cl2 / Ambient temperature; 2-3 h 6: 1.) NaBH4; 2.) MnO2 / 1.) PdCl2(PPh)2 / 1.) methanol, 15 min; 2.) DCM, 30 min View Scheme

1: 95 percent / 10percent NaOH / 1 h / Heating 2: 80 percent / HCl / 4 h 3: 1.) 6N HCl, sodium nitrite / 1.) -10 deg C; 2.) dioxane, water, 80 deg C, 10 min 4: 85 percent / MnO2 / CH2Cl2 / Ambient temperature; 2-3 h 5: 1.) NaBH4; 2.) MnO2 / 1.) PdCl2(PPh)2 / 1.) methanol, 15 min; 2.) DCM, 30 min View Scheme

1: 1.) 6N HCl, sodium nitrite / 1.) -10 deg C; 2.) dioxane, water, 80 deg C, 10 min 2: 85 percent / MnO2 / CH2Cl2 / Ambient temperature; 2-3 h 3: 1.) NaBH4; 2.) MnO2 / 1.) PdCl2(PPh)2 / 1.) methanol, 15 min; 2.) DCM, 30 min View Scheme