[1,3-bis(diphenylphosphino)propane]dichloro nickel (II) in tetrahydrofuran; diethyl ether 96 h; Ambient temperature;

1: 74 percent / complex of CuI with 2,2'-bipyridyl / tetrahydrofuran / 1) 2 deg C, 2 h, 2) 20 deg C, 15 h 2: 1) ozone-oxygen mixture, 2) H2 / 2) Pd-CaCO3-PbO / 1) methanol, 0 deg C, 2) methanol, RT, 25 h 3: 85 percent / p-TsOH / methanol; H2O / 20 h / Ambient temperature 4: 91 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 5: 46 percent / piperidine, pyridine / 1) 22 deg C, 17 h, 2) 30 deg C, 6 h, then 120 deg C, 1.5 h View Scheme

[2,2']bipyridinyl; copper(l) iodide 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 4 h, b) 20 deg C, 15 h; Yield given. Multistep reaction;

1: 74 percent / complex of CuI with 2,2'-bipyridyl / tetrahydrofuran / 1) 2 deg C, 2 h, 2) 20 deg C, 15 h 2: 1) ozone-oxygen mixture, 2) H2 / 2) Pd-CaCO3-PbO / 1) methanol, 0 deg C, 2) methanol, RT, 25 h 3: 85 percent / p-TsOH / methanol; H2O / 20 h / Ambient temperature 4: 91 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 1.) CuI, 2,2'-bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 4 h, b) 20 deg C, 15 h 2: 10.7 g / pyridine / 1.) -5 deg C, 6 h, 2.) 0 deg C, 12 h 3: 82 percent / NaBr / dimethylformamide / 2 h / 65 °C View Scheme

1: 1.) CuI, 2,2'-bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 4 h, b) 20 deg C, 15 h 2: 10.7 g / pyridine / 1.) -5 deg C, 6 h, 2.) 0 deg C, 12 h 3: 82 percent / NaBr / dimethylformamide / 2 h / 65 °C 4: 69 percent / PdCl2, CuCl, O2 / dimethylformamide; H2O / 24 h 5: 81 percent / Py*TsOHY / benzene View Scheme

2: 85 percent / pyridine / benzene / 3 h / Ambient temperature 3: 1.) BH3*THF, 2.) 5 N NaOH, 29 percent H2O2 / 1.) room temperature, 2 h, 2.) room temperature, 2 h 4: 2 N HCl View Scheme

1: 1.) CuI, 2,2'-bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 4 h, b) 20 deg C, 15 h 2: 10.7 g / pyridine / 1.) -5 deg C, 6 h, 2.) 0 deg C, 12 h 3: 82 percent / NaBr / dimethylformamide / 2 h / 65 °C 4: 69 percent / PdCl2, CuCl, O2 / dimethylformamide; H2O / 24 h 5: 81 percent / Py*TsOHY / benzene 6: 1.) Li, FeCl3, liq. NH3 / 1.) -35 deg C, 0.3 h, 2.) THF, DMSO, -35 deg C, 4.5 h 7: 1.) EtMgBr, 2.) CuI 8: O3 / cyclohexane; acetic acid / 5 °C 9: aq. H2Cr2O4 / acetone / 4 h / 20 °C 10: 10percent aq. HCl / acetone / 6 h / 20 °C 11: 85 percent / NaBH4 / ethanol / 0.17 h View Scheme

1: 1.) CuI, 2,2'-bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 4 h, b) 20 deg C, 15 h 2: 10.7 g / pyridine / 1.) -5 deg C, 6 h, 2.) 0 deg C, 12 h 3: 82 percent / NaBr / dimethylformamide / 2 h / 65 °C 4: 69 percent / PdCl2, CuCl, O2 / dimethylformamide; H2O / 24 h 5: 81 percent / Py*TsOHY / benzene 6: 1.) Li, FeCl3, liq. NH3 / 1.) -35 deg C, 0.3 h, 2.) THF, DMSO, -35 deg C, 4.5 h 7: 1.) EtMgBr, 2.) CuI 8: O3 / cyclohexane; acetic acid / 5 °C 9: aq. H2Cr2O4 / acetone / 4 h / 20 °C 10: 10percent aq. HCl / acetone / 6 h / 20 °C 11: 85 percent / NaBH4 / ethanol / 0.17 h 12: 93 percent / NaBH4, NaOH, Ni(OAc)2*4H2), ethylene diamine, H2 / ethanol / 2 h / 20 °C View Scheme

1: 1.) CuI, 2,2'-bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 4 h, b) 20 deg C, 15 h 2: 10.7 g / pyridine / 1.) -5 deg C, 6 h, 2.) 0 deg C, 12 h 3: 82 percent / NaBr / dimethylformamide / 2 h / 65 °C 4: 69 percent / PdCl2, CuCl, O2 / dimethylformamide; H2O / 24 h 5: 81 percent / Py*TsOHY / benzene 6: 1.) Li, FeCl3, liq. NH3 / 1.) -35 deg C, 0.3 h, 2.) THF, DMSO, -35 deg C, 4.5 h 7: 1.) EtMgBr, 2.) CuI 8: O3 / cyclohexane; acetic acid / 5 °C 9: aq. H2Cr2O4 / acetone / 4 h / 20 °C 10: 10percent aq. HCl / acetone / 6 h / 20 °C 11: 85 percent / NaBH4 / ethanol / 0.17 h 12: 93 percent / NaBH4, NaOH, Ni(OAc)2*4H2), ethylene diamine, H2 / ethanol / 2 h / 20 °C 13: 30 percent / 2,2'-dipyridil disulfide, PPh3 / acetonitrile / 2 h / 20 °C View Scheme