diethyl ether; ammonia; sodium amide

1: 87 percent / Pd(PPh3)4 / tetrahydrofuran / 8 h / 0 °C 2: aq. KF / dimethylformamide / 5 h / Ambient temperature 3: 1.) bis(cyclopentadienyl)zirconium chloride hydride, 2.) PdCl2(PPh3)2, DIBAH / 1.) benzene, RT, 0.5 h, 2.) benzene, hexane, THF, RT, 20.5 h View Scheme

tetrakis(triphenylphosphine) palladium(0) in toluene T=60°C; 3 h;

1: 87 percent / Pd(PPh3)4 / tetrahydrofuran / 8 h / 0 °C 2: aq. KF / dimethylformamide / 5 h / Ambient temperature 3: 1.) bis(cyclopentadienyl)zirconium chloride hydride, 2.) PdCl2(PPh3)2, DIBAH / 1.) benzene, RT, 0.5 h, 2.) benzene, hexane, THF, RT, 16 h View Scheme