1: sulfuric acid; nitric acid / 7.08 h / 0 - 50 °C / |Inert atmosphere; |Sealed tube 2: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 4 h / -78 - 0 °C / |Inert atmosphere 3: iron; acetic acid / methanol / 2 h / |Reflux; |Inert atmosphere 4: N-bromosuccinmide / acetonitrile / 4 h / 0 - 20 °C / |Inert atmosphere 5: tetrakis(triphenylphosphine) palladium(0); cesium fluoride; copper(l) iodide / toluene / 110 °C / |Inert atmosphere 6: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / 1,4-dioxane; water / 110 °C 7: ammonium cerium (IV) nitrate / acetonitrile; water / 0 °C 8: bromine / chloroform / 8 h / 20 °C / |Darkness; |Inert atmosphere 9: sodium azide / N,N-dimethyl-formamide / 0 °C / |Inert atmosphere 10: hydrogen; palladium on activated charcoal / methanol; ethyl acetate View Scheme

1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 4 h / -78 - 0 °C / |Inert atmosphere 2: iron; acetic acid / methanol / 2 h / |Reflux; |Inert atmosphere 3: N-bromosuccinmide / acetonitrile / 4 h / 0 - 20 °C / |Inert atmosphere 4: tetrakis(triphenylphosphine) palladium(0); cesium fluoride; copper(l) iodide / toluene / 110 °C / |Inert atmosphere 5: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / 1,4-dioxane; water / 110 °C 6: ammonium cerium (IV) nitrate / acetonitrile; water / 0 °C 7: bromine / chloroform / 8 h / 20 °C / |Darkness; |Inert atmosphere 8: sodium azide / N,N-dimethyl-formamide / 0 °C / |Inert atmosphere 9: hydrogen; palladium on activated charcoal / methanol; ethyl acetate View Scheme

1: iron; acetic acid / methanol / 2 h / |Reflux; |Inert atmosphere 2: N-bromosuccinmide / acetonitrile / 4 h / 0 - 20 °C / |Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); cesium fluoride; copper(l) iodide / toluene / 110 °C / |Inert atmosphere 4: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / 1,4-dioxane; water / 110 °C 5: ammonium cerium (IV) nitrate / acetonitrile; water / 0 °C 6: pyridine; bromine / chloroform / 8 h / 20 °C / |Darkness; |Inert atmosphere 7: sodium azide / N,N-dimethyl-formamide / 0 °C / |Inert atmosphere 8: hydrogen; palladium on activated charcoal / methanol; ethyl acetate View Scheme

1: tetrakis(triphenylphosphine) palladium(0); cesium fluoride; copper(l) iodide / toluene / 110 °C / |Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium phosphate / 1,4-dioxane; water / 110 °C 3: ammonium cerium (IV) nitrate / acetonitrile; water / 0 °C 4: bromine / chloroform / 8 h / 20 °C / |Darkness; |Inert atmosphere 5: sodium azide / N,N-dimethyl-formamide / 0 °C / |Inert atmosphere 6: hydrogen; palladium on activated charcoal / methanol; ethyl acetate View Scheme

1.1: 2,6-di-tert-butyl-4-methylpyridine / hexafluoroisopropyl alcohol; dichloromethane / 4 h / -50 - 20 °C / Inert atmosphere 2.1: N-bromosuccinmide / acetonitrile / 0 - 20 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium(0); hexamethyl-distannane / toluene / 16 h / 60 °C / Inert atmosphere 3.2: 16 h / 110 °C / Inert atmosphere 4.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 16 h / 110 °C / Inert atmosphere 5.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0 - 20 °C / Darkness 6.1: pyridine; bromine / chloroform / 8 h / 20 °C / Darkness; Inert atmosphere 7.1: sodium azide / N,N-dimethyl-formamide / 3 h / 0 °C / Darkness; Inert atmosphere 8.1: palladium 10 on activated carbon; hydrogen / methanol; ethyl acetate / 4 h / 20 °C / Darkness; Inert atmosphere View Scheme