1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; ethylene glycol dimethyl ether / 12 h / 85 °C / |Inert atmosphere 2: diisobutylaluminium hydride / toluene; dichloromethane / 1.5 h / -78 °C / |Inert atmosphere 3: [bis(acetoxy)iodo]benzene; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / dichloromethane / 20 °C View Scheme

Multistep reaction;

1: diethyl ether View Scheme

sulfur; lithium chloride; zinc Yield given. Multistep reaction. Yields of byproduct given;

potassium hydroxide; hydrazine in ethylene glycol Heating;