pyridine; 4-(N,N-dimethlyamino)pyridine in dichloromethane 1 h; Ambient temperature;

1: 69 percent / tri-n-butylphosphine / CH2Cl2 / 0.5 h / 0 °C 2: siver(I) triflate / diethyl ether / 2 h / Ambient temperature 3: 85 percent / H2 / 10percent Pd/C / tetrahydrofuran / 12 h / 25 °C View Scheme

1: siver(I) triflate / diethyl ether / 2 h / Ambient temperature 2: 85 percent / H2 / 10percent Pd/C / tetrahydrofuran / 12 h / 25 °C View Scheme

bis(1,5-cyclooctadiene)nickel (0); NH4Br; (R,R)-Ph-pybox; zinc in N,N-dimethyl acetamide T=25°C; 12 h; Inert atmosphere;

hydrogen; palladium 1) methanole, ethyl acetate, 2) pyridine, 12 h, RT; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;