1: 1) Li2CuCl4 / 1) THF, -78 deg C, 2) THF, a) -78 deg C, 1 h, b) -10 deg C, 2 h, c) room temp., 10 h 2: acetic acid / 24 h / Ambient temperature View Scheme

1: 53.87 percent / LiCuCl4 / tetrahydrofuran / 3 h / -10 °C 2: 87.2 percent / pyridinium p-toluenesulphonate / methanol / 4 h / 55 °C 3: 76.08 percent / PBr3, pyridine / diethyl ether / 2 h / Heating 4: 47.8 percent / Li2CuCl4 / tetrahydrofuran / 3 h / -10 °C View Scheme

1: 53.87 percent / LiCuCl4 / tetrahydrofuran / 3 h / -10 °C 2: 87.2 percent / pyridinium p-toluenesulphonate / methanol / 4 h / 55 °C View Scheme

1: 76 percent / PdCl2(PPh3)2 / diethyl ether; tetrahydrofuran / 1 h / Ambient temperature 2: 1.) NiCl2(Ph2PCH2CH2PPh2) / 1.) ether, 12 h, room temp., 2.) 80 deg C, 15 h View Scheme