1.1: 85 percent / PPh3; I2; imidazole / CH2Cl2 2.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C 2.2: ZnBr2 / tetrahydrofuran; diethyl ether; pentane / -78 - 0 °C 2.3: 91 percent / Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; diethyl ether; pentane / 2 h / 23 °C 3.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C 3.2: ZnBr2 / tetrahydrofuran; diethyl ether / -78 - 0 °C 3.3: 90 percent / Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; diethyl ether; pentane / 23 °C 4.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C 4.2: ZnBr2 / tetrahydrofuran; diethyl ether / -78 - 0 °C 4.3: 79 percent / Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; pentane; diethyl ether / 23 °C 5.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C 5.2: ZnBr2 / tetrahydrofuran; diethyl ether / -78 - 0 °C 5.3: 83 percent / Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; diethyl ether; pentane / 23 °C 6.1: 81 percent / KOH; H2O / methanol / 2 h / Heating 7.1: Cl2ZrCp2 / 1,2-dichloro-ethane / 8 h / 23 °C 7.2: 88 percent / I2 / tetrahydrofuran; 1,2-dichloro-ethane / 0.25 h / 0 °C 8.1: t-BuLi / diethyl ether; pentane / -78 °C 8.2: ZnBr2 / diethyl ether; tetrahydrofuran / -78 - 0 °C 8.3: Cl2Pd(dppf)(CH2Cl2) / tetrahydrofuran; diethyl ether; pentane / 23 °C 9.1: 84 percent / KOH / methanol; H2O / Heating 10.1: Cl2ZrCp2 / 1,2-dichloro-ethane / 1 h / 23 °C 10.2: 90 percent / Cl2Ni(PPh)2; n-BuLi; PPh3 / tetrahydrofuran / 1 h / 23 °C View Scheme

1.1: imidazole / tetrahydrofuran / 1 h / 20 °C 2.1: magnesium / tetrahydrofuran / 1 h / 70 °C 2.2: ZnCl2 / tetrahydrofuran / 1 h / 20 °C 2.3: Pd(PPh3)4 / tetrahydrofuran / 16 h / 20 °C 3.1: 1.84 g / Bu4NF / tetrahydrofuran / 2 h / 20 °C 4.1: 65 percent / CrO3; H2SO4 / H2O; acetone / 0.25 h / 0 °C View Scheme