lithium iodide in various solvent(s) 18 h; Heating;

in tetrahydrofuran T=-78°C; 1 h;

pyrrolidine; tetrakis(triphenylphosphine) palladium(0) T=82°C; 3 h;

1: ortho-ethylanisole With n-butyllithium in tetrahydrofuran T=-78°C; 1 h; 2: methyl iodide in tetrahydrofuran T=-78°C; 1 h;

t-Bu-XantPhos; dichloro bis(acetonitrile) palladium(II); potassium carbonate; cesium fluoride in toluene T=100°C; 20 h; Inert atmosphere;

in tetrahydrofuran T=-78°C; 5 h; Reflux;

1: With diethylzinc; oxygen in n-heptane; dichloromethane T=20°C; 14 h; Darkness; 2: With ammonium chloride in n-heptane; dichloromethane; water Overall yield = 48 percent;

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 2: tetrahydrofuran / 1 h / -78 °C View Scheme

1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine / 5 h / Reflux 2.1: potassium hydroxide / toluene / 1.5 h / Reflux 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: 5 h / -78 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 5.1: tetrahydrofuran / 1 h / -78 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 5 h / -78 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 3.1: tetrahydrofuran / 1 h / -78 °C View Scheme