Cu(I) 3-methylsalicylate; bis(dibenzylideneacetone)-palladium(0) in N,N-dimethyl-formamide T=45 - 50°C; Sonogashira coupling; 12 h;

1: propynoic acid ethyl ester With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 2: With zinc dibromide in tetrahydrofuran T=-78 - 20°C; 9 h; 3: 1-iodo-2-methoxybenzene With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene in tetrahydrofuran T=50°C; Negishi cross-coupling reaction; Inert atmosphere;

1: ortho-anisaldehyde With TMSC(Li)N2 in tetrahydrofuran; hexane T=-78 - 20°C; 1.5 h; 2: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.5 h; 3: chloroformic acid ethyl ester in tetrahydrofuran; hexane T=-78°C; 0.5 h; Further stages.;

potassium carbonate in methanol T=60°C; 4 h;

1: silver(I) acetate / N,N-dimethyl-formamide / 40 h / 70 °C / Darkness 2: Cu(I) 3-methylsalicylate; bis(dibenzylideneacetone)-palladium(0) / N,N-dimethyl-formamide / 12 h / 45 - 50 °C View Scheme

4-(N,N-dimethlyamino)pyridine in dichloromethane T=0 - 25°C; Inert atmosphere; optical yield given as percent de;

1: 73 percent / Et3N / toluene / 3 h / Ambient temperature 2: 88 percent / 500 °C / 0.1 - 1 Torr View Scheme

1: thionyl chloride / 8 h / 25 °C / neat (no solvent) 2: 4-(N,N-dimethlyamino)pyridine / dichloromethane / 0 - 25 °C / Inert atmosphere View Scheme

1: 1-ethynyl-2-methoxybenzene With n-butyllithium 2: chloroformic acid ethyl ester

water; potassium hydroxide in methanol T=25°C; 12 h;