PPh3 gold(I) chloro complex; silver trifluoromethanesulfonate in tetrahydrofuran T=50°C; 1 h; Inert atmosphere; regioselective reaction;

nickel in ethanol; acetone 0.5 h; Ambient temperature;

1: 53 percent / Et2NH; CuI / Pd(PPh3)2Cl2 / 4 h / 20 °C 2: 23 percent / KI / PdI2 / N,N-dimethyl-acetamide / 18 h / 80 °C View Scheme

1: 92 percent / tetrahydrofuran / 1 h, -70 deg C, than 1 h, r.t. 2: 91 percent / HCl / methanol; H2O / 1 h / Ambient temperature 3: 93 percent / BuLi / tetrahydrofuran / -10 °C 4: 54 percent / Raney Ni / ethanol / 0.5 h / Ambient temperature View Scheme

1: 93 percent / BuLi / tetrahydrofuran / -10 °C 2: 54 percent / Raney Ni / ethanol / 0.5 h / Ambient temperature View Scheme

1: 91 percent / HCl / methanol; H2O / 1 h / Ambient temperature 2: 93 percent / BuLi / tetrahydrofuran / -10 °C 3: 54 percent / Raney Ni / ethanol / 0.5 h / Ambient temperature View Scheme