1: sodium hydride / toluene; mineral oil / |Reflux 2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 50 °C / |Inert atmosphere 3: phosphorus trichoride / N,N-dimethyl-formamide / 1 h / -20 °C View Scheme

1: 4,4-dimethyl-6-bromothiochromane S-oxide With potassium carbonate; copper(l) iodide; palladium 10 on activated carbon; triphenylphosphine in ethylene glycol dimethyl ether; water T=20°C; 0.5 h; 2: 2-methyl-but-3-yn-2-ol in ethylene glycol dimethyl ether; water T=80°C; 5 h;

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 - 20 °C 2.1: potassium carbonate; copper(l) iodide; triphenylphosphine; palladium 10 on activated carbon / ethylene glycol dimethyl ether; water / 0.5 h / 20 °C 2.2: 5 h / 80 °C View Scheme

sodium hydride in toluene T=110°C; 1 h;

sodium hydride in toluene T=110°C; 1 h;