N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0); silver(I) in N,N-dimethyl-formamide

1: 1-(trimethylsilyl)-1,7-octadiyne With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.166667 h; 2: triisopropylsilyl chloride in tetrahydrofuran; hexane T=-78 - 20°C;

1: 92 percent / PdCl2(PPh3)2; CuI; N,N-diisopropylethylamine / dimethylformamide / 20 °C 2: 85 percent / TBAF / tetrahydrofuran / 3 h / 0 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 1.08 h / -78 - -30 °C 1.2: tetrahydrofuran; hexane / 12 h / -78 - 20 °C 2.1: tetrahydrofuran; hexane / -78 - 20 °C View Scheme