[bis(acetoxy)iodo]benzene; triethylamine; potassium iodide; copper(l) iodide in acetonitrile T=20°C; 0.3 h;

1: triiodomethane With sodium hexamethyldisilazane in tetrahydrofuran; diethyl ether T=-78 - -20°C; 1 h; Inert atmosphere; 2: p-methylbenzyl bromide in tetrahydrofuran; diethyl ether T=-20°C; 5 h; Inert atmosphere; 3: With potassium tert-butylate in tetrahydrofuran; diethyl ether T=-20 - 20°C; 12 h; Inert atmosphere;

N-iodo-succinimide; tetrabutyl-ammonium trifluoroacetate in 1,2-dichloro-ethane T=20°C; iododecarboxylation; 0.25 h;

copper(l) iodide in acetonitrile T=40°C; 24 h;

N-iodo-succinimide; silver nitrate in N,N-dimethyl-formamide 24 h; Darkness;

potassium carbonate; palladium dichloride in methanol; water; toluene T=100°C; Sonogashira coupling; 8 h;

tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide T=20°C; 3 h;

1: (3-dibromomethylene-penta-1,4-diynyl)-benzene With n-butyllithium in hexane; toluene T=-40 - -20°C; Fritsch-Buttenburg-Wiechell rearrangement; 2: With zinc(II) chloride in tetrahydrofuran; hexane; toluene T=-40 - 0°C; 3: 1-(1-iodoethynyl)-4-methylbenzene With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran; hexane; toluene T=70°C; Negishi coupling; 20 h;

bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; trimethylsilylacetylene T=25°C; 14 h;

bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine T=25°C; 14 h;