1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere 1.2: 1 h / 20 °C / Inert atmosphere 2.1: methanol; copper(l) iodide / N,N-dimethyl-formamide / 10 h / 120 °C / Inert atmosphere 3.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.25 h / 0 °C / Inert atmosphere 4.1: bromine; triphenylphosphine / dichloromethane / 4 h / 20 °C / Inert atmosphere 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 6.1: hydrogen / methanol / 3 h / 20 °C / 3102.97 Torr View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere 1.2: 1 h / 20 °C / Inert atmosphere 2.1: copper(l) iodide / methanol; N,N-dimethyl-formamide / 10 h / 120 °C / Inert atmosphere 3.1: toluene-4-sulfonic acid / tetrahydrofuran / 0.25 h / Reflux; Inert atmosphere 4.1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 5.1: palladium diacetate; potassium carbonate; triphenylphosphine / N,N-dimethyl-formamide / 7 h / 120 °C / Inert atmosphere 6.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 20 °C / Inert atmosphere 7.1: hydrogen; palladium(II) oxide hydrate / methanol / 4 h / 3102.97 Torr View Scheme

1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); tri-n-butyl-tin hydride / N,N-dimethyl-formamide / 0.75 h / 100 °C / Inert atmosphere 3: methanol; copper(l) iodide / N,N-dimethyl-formamide / 5 h / 120 °C / Inert atmosphere View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C / Inert atmosphere 1.2: 1 h / 20 °C / Inert atmosphere 2.1: copper(l) iodide / methanol; N,N-dimethyl-formamide / 10 h / 120 °C / Inert atmosphere 3.1: toluene-4-sulfonic acid / tetrahydrofuran / 0.25 h / Reflux; Inert atmosphere 4.1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 5.1: palladium diacetate; potassium carbonate; triphenylphosphine / N,N-dimethyl-formamide / 7 h / 120 °C / Inert atmosphere 6.1: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 20 °C / Inert atmosphere View Scheme