N-butylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) in benzene 6 h; Ambient temperature;

1: 2-chloro-4-phenyl-1-buten-3-yne With lithium diisopropyl amide in tetrahydrofuran; hexane T=-78 - -30°C; 1 h; Inert atmosphere; 2: With zinc dibromide in tetrahydrofuran; hexane T=-30 - 0°C; 0.5 h; Inert atmosphere; 3: trans-3-iodo-2-propen-1-ol With tetrakis(triphenylphosphine) palladium(0); diethylzinc in tetrahydrofuran; hexane; N,N-dimethyl-formamide T=0 - 60°C; Negishi Coupling; 6 h; Inert atmosphere;

1: 2-chloro-4-phenyl-1-buten-3-yne With lithium diisopropyl amide in tetrahydrofuran; hexane T=-78 - -30°C; 1 h; Inert atmosphere; 2: With zinc dibromide in tetrahydrofuran; hexane T=-30 - 0°C; 0.5 h; Inert atmosphere; 3: 2-Iodothiophene With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran; hexane T=0 - 23°C; Negishi Coupling; 3 h; Inert atmosphere;

1: 2-chloro-4-phenyl-1-buten-3-yne With n-butyllithium; diisopropylamine in tetrahydrofuran; hexane T=-78 - -30°C; 1 h; 2: With zinc dibromide in tetrahydrofuran; hexane T=-30 - 0°C; 0.5 h; 3: benzyl bromide With [Pd{bis[2-(diphenylphosphino)phenyl] ether}Cl2] in tetrahydrofuran; hexane T=23°C; 3 h;