1: potassium fluoride / methanol / 16 h / 20 °C 2: Na2S*9H2O; potassium hydroxide / methanol / 2 h / 120 °C / Microwave irradiation View Scheme

bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine in tetrahydrofuran T=65°C; Sonogashira coupling; 12 h; Inert atmosphere;

tetrakis(triphenylphosphine) palladium(0); ethylmagnesium bromide 1.) THF, reflux, 1 h; 2.) benzene, THF, 60 deg C, 5 h.; Multistep reaction;

1: 1.) sat. HgCl2, 20percent aq. sodium acetate, 2.) I2 / 1.) ethanol, water, 40 deg C, 20 h, 2.) CHCl3, rt. 2 h. 2: 1.) EtMgBr, 2.) (PPh3)4Pd / 1.) THF, reflux, 1 h; 2.) benzene, THF, 60 deg C, 5 h. View Scheme

1: copper(l) iodide; sodium iodide; N-methyl-2-(methylamino)ethylamine / 105 °C 2: copper(l) iodide; Pd2(PPh3)2Cl2; triethylamine / N,N-dimethyl-formamide / 1.5 h / 20 °C / Inert atmosphere View Scheme