1: 95 percent / 5percent HCl / acetone / 6 h / Ambient temperature 2: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 3: 85 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 4: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 5: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C View Scheme

1: 90 percent / CuI / diethyl ether 2: 95 percent / 5percent HCl / acetone / 4 h / Ambient temperature View Scheme

1: Li2CuCl4 / 1) THF -78 deg C, 2 hours 2) room temperature 15 h 2: 11.7 g / 5percent aq. HCl / acetone / 6 h / Ambient temperature 3: diisobutylaluminum hydride / diethyl ether / 1.5 h / -10 °C 4: 43 percent / pyridine / diethyl ether / 12 h / Ambient temperature; 1) 5 deg C, 1 h 2) room temperature 12 h 5: CuI, 2,2'-bipyridyl / 2 deg C, 2 h, THF View Scheme

1: 85 percent / NaI, zinc dust / bis-(2-methoxy-ethyl) ether / 1.5 h / 65 - 70 °C 2: 95 percent / 5percent aq. HCl / acetone / 6 h / Ambient temperature 3: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C 4: 90 percent / triphenylphosphine, bromine / CCl4 / 1) 15 deg C, 1 h; 2) room temp., 15 h. 5: 1) cuprous iodide, 2,2'-bipyridyl 2) Mg / 1) abs. THF, 20 deg C, 0.5 h; 2) abs. THF, 2 h at 2 deg C and 15 h at room temp. 6: 1) p-toluenesulfonic acid, water; 2) pyridine / 1) MeOH, room temp., 15 h; 2) room temp., 24 h. View Scheme

1: 63 percent / dilithium tetrachlorocuprate / tetrahydrofuran / 1.) -78 deg C, 2 h, 2.) RT, 15 h 2: 99 percent / 5percent HCl / acetone / 6 h / Ambient temperature 3: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 4: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 5: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 6: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C 7: 94 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature View Scheme

1: 95 percent / 5percent HCl / acetone / 6 h / Ambient temperature 2: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 3: 85 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 4: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 5: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C 6: 91 percent / pyridine / 24 h / Ambient temperature View Scheme

1: 90 percent / CuI / diethyl ether 2: 95 percent / 5percent HCl / acetone / 4 h / Ambient temperature View Scheme

copper(l) iodide in diethyl ether 2 h at 5 deg C, then 2 h at room temp.;

Yield given. Multistep reaction;

pyridine T=-10°C; 15 h;