1: Grubb's 2nd generation catalyst / dichloromethane / Reflux 2: palladium 10 on activated carbon; oxygen / toluene / Molecular sieve; Reflux View Scheme

Grubb's 2nd generation catalyst in dichloromethane Reflux;

<b>Multi-step reaction with 2 steps<br /> </b>1: iodine / dichloromethane / 24 h / 20 &deg;C<br />2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride / N,N-dimethyl-formamide / 100 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1.1: n-butyllithium / tetrahydrofuran / -78 - 20 &deg;C<br />2.1: manganese(IV) oxide / dichloromethane / 0 - 20 &deg;C<br />2.2: 50 &deg;C<br />3.1: iodine / methanol / 5 h / 20 &deg;C<br />4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride / N,N-dimethyl-formamide / 100 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1.1: toluene-4-sulfonic acid / dichloromethane / 20 &deg;C<br />2.1: n-butyllithium / tetrahydrofuran / -78 - 20 &deg;C<br />3.1: manganese(IV) oxide / dichloromethane / 0 - 20 &deg;C<br />3.2: 50 &deg;C<br />4.1: iodine / methanol / 5 h / 20 &deg;C<br />5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride / N,N-dimethyl-formamide / 100 &deg;C<br /> <br /> &nbsp;