1: carbon tetrabromide With triphenylphosphine; zinc in dichloromethane T=20°C; 0.5 h; 2: oct-2-ynal in dichloromethane T=20°C;

tetrakis(triphenylphosphine) palladium(0); tri-n-butyl-tin hydride in toluene T=20°C; 1 h;

1: 40 percent / tributyltin hydride; Pd(PPh3)4 / toluene / 1 h / 20 °C 2: 63 percent / CuI; NaI; N,N'-dimethylethylenediamine / butan-1-ol / 48 h / 120 °C View Scheme