n-butyllithium; tetrakis (triphenylphosphine) palladium (0); zinc(II) chloride in tetrahydrofuran; hexane; ethyl acetate

1: 2-Chloro-5-pyridinecarboxylicacid ethylester With potassium carbonate; triphenylphosphine; 5-palladium/activated carbon in toluene T=45 - 50°C; 2: (4,4-dimethylthiochroman-6-yl)acetylene With copper(l) iodide in toluene T=45 - 115°C; Product distribution / selectivity;

copper(l) iodide; potassium carbonate; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine in tetrahydrofuran 5 h; Heating / reflux; Product distribution / selectivity;

sulfuric acid Heating / reflux;

in ethyl acetate; triethylamine

in toluene T=110 - 120°C; Product distribution / selectivity;

in toluene T=110 - 120°C; Product distribution / selectivity;

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 3.1: sodium hydride / toluene; mineral oil / |Reflux 4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 50 °C / |Inert atmosphere 5.1: phosphorus trichoride / N,N-dimethyl-formamide / 1 h / -20 °C View Scheme

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