1: trimethylsilylacetylene With methylmagnesium bromide; zinc dibromide in tetrahydrofuran T=0°C; 0.5 h; 2: 1-bromo-2-iodoethylene With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=20°C; 3 h; Further stages.;

potassium hydroxide; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=60°C; Suzuki cross-coupling; 10 h;

1: anhydrous 1-octyne; trimethylaluminum With zirconocene dichloride in dichloromethane T=23°C; 6 h; 2: With indium(III) chloride in tetrahydrofuran; dichloromethane T=0°C; 0.5 h; 3: 1-bromo-2-iodoethylene With trifuran-2-yl-phosphane; Cl2Pd[bis(2-diphenylphosphinophenyl)ether]; diisobutylaluminium hydride in tetrahydrofuran; hexane; dichloromethane T=0°C; 4 h;

1: anhydrous 1-octyne With diisobutylaluminium hydride in n-heptane T=50°C; 4 h; 2: With indium(III) chloride in tetrahydrofuran; n-heptane T=0°C; 0.5 h; 3: 1-bromo-2-iodoethylene With trifuran-2-yl-phosphane; Cl2Pd[bis(2-diphenylphosphinophenyl)ether]; diisobutylaluminium hydride in tetrahydrofuran; hexane; n-heptane T=0°C; 4 h;

1: trans-1-iodo-1-octene With tert.-butyl lithium in diethyl ether; pentane T=-78°C; 0.5 h; 2: With zinc dibromide in tetrahydrofuran; diethyl ether; pentane T=-78 - 0°C; 0.5 h; 3: 1-bromo-2-iodoethylene With trifuran-2-yl-phosphane; Cl2Pd[bis(2-diphenylphosphinophenyl)ether]; diisobutylaluminium hydride in tetrahydrofuran; diethyl ether; hexane T=0°C; 4 h;

1: trimethylaluminum; 1-((E,E,E)-3-methyl-1,3,5-octatrien-7-ynyl)-2,6,6-trimethyl-1-cyclohexene With zirconocene dichloride in dichloromethane T=23°C; 4 h; 2: T=50°C; 3: 1-bromo-2-iodoethylene With tris(dibenzylideneacetone)dipalladium (0); zinc(II) chloride in tetrahydrofuran; N,N-dimethyl-formamide T=23°C; 8 h; Further stages.;

potassium hydroxide; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=60°C; Suzuki cross-coupling; 10 h; Product distribution; Further Variations:Reaction partners;

potassium hydroxide; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=60°C; Suzuki cross-coupling; 10 h;

potassium hydroxide; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=60°C; Suzuki cross-coupling; 10 h; Product distribution; Further Variations:Reaction partners;

1: iodobenzene With tert.-butyl lithium in diethyl ether; pentane T=-78°C; 0.5 h; 2: With zinc dibromide in tetrahydrofuran; diethyl ether; pentane T=-78 - 0°C; 0.5 h; 3: 1-bromo-2-iodoethylene With trifuran-2-yl-phosphane; Cl2Pd[bis(2-diphenylphosphinophenyl)ether]; diisobutylaluminium hydride in tetrahydrofuran; diethyl ether; hexane T=0°C; 4 h;