1: 1.) n-BuLi / 1) THF, hexane, 0.5 h; 2) THF, hexane, 30 deg C, 2 h 2: 1.) n-BuLi / 1) THF, hexane, 0.5 h; 2) THF, hexane, 30 deg C, 2 h 3: 0.666 g / aq. HCl / diethyl ether / 0.17 h 4: 95 percent / NaBH4 / methanol 5: triethylamine / CH2Cl2 / 1) 0 deg C, 0.5 h; 2) 30 deg C, 4 h 6: 96 percent / LAH / diethyl ether / 1) 0 deg C, 0.5 h; 2) 30 deg C, 1 h View Scheme

copper (I) cyanide; lithium chloride 1.) THF, ether, -10 deg C, 2.) a) -10 deg C, 1 h, b) 0 deg C, 2 h, c) RT, 1 h; Yield given. Multistep reaction;

[2,2']bipyridinyl; copper(l) iodide 2 deg C, 2 h, THF; Yield given. Multistep reaction;

1: 86 percent / dimethylsulfoxide / Ambient temperature 2: KOH / ethane-1,2-diol / 6 h / Heating 4: 90 percent / lithium aluminium hydride / diethyl ether / 3 h / Ambient temperature 5: 74 percent / pyridine / 24 h / Ambient temperature View Scheme

1: 86 percent / dimethylsulfoxide / Ambient temperature 2: KOH / ethane-1,2-diol / 6 h / Heating 4: 90 percent / lithium aluminium hydride / diethyl ether / 3 h / Ambient temperature View Scheme