1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 2: palladium diacetate; potassium carbonate; triphenylphosphine / N,N-dimethyl-formamide / 7 h / 120 °C / Inert atmosphere 3: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 20 °C / Inert atmosphere 4: hydrogen; palladium(II) oxide hydrate / methanol / 4 h / 3102.97 Torr View Scheme

1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 2: palladium diacetate; potassium carbonate; triphenylphosphine / N,N-dimethyl-formamide / 7 h / 120 °C / Inert atmosphere 3: ammonium cerium (IV) nitrate / water; acetonitrile / 2 h / 20 °C / Inert atmosphere View Scheme

<b>Multi-step reaction with 4 steps<br /> </b>1.1: N-bromosuccinmide / N,N-dimethyl-formamide / 20 &deg;C / Inert atmosphere<br />2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 &deg;C / Inert atmosphere<br />2.2: 1 h / 20 &deg;C / Inert atmosphere<br />3.1: copper(l) iodide / methanol; N,N-dimethyl-formamide / 10 h / 120 &deg;C / Inert atmosphere<br />4.1: toluene-4-sulfonic acid / tetrahydrofuran / 0.25 h / Reflux; Inert atmosphere<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 &deg;C / Inert atmosphere<br />1.2: 1 h / 20 &deg;C / Inert atmosphere<br />2.1: copper(l) iodide / methanol; N,N-dimethyl-formamide / 10 h / 120 &deg;C / Inert atmosphere<br />3.1: toluene-4-sulfonic acid / tetrahydrofuran / 0.25 h / Reflux; Inert atmosphere<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '472690', constants.ctx, '0')">toluene-4-sulfonic acid</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />0.25&nbsp;h;&nbsp;&nbsp;RefluxInert atmosphere;&nbsp;<br /> <br /> &nbsp;