ammonium cerium(IV) nitrate in water; acetonitrile 0.5 h; Ambient temperature;

1: 100 percent / pyridine / Ambient temperature 2: 1.) NaH / 1.) benzene, reflux, 2 h, 2.) benzene, reflux, overnight 3: 56 percent / pyridine / Ambient temperature 4: 100 percent / CoCl2, NaBH4 / tetrahydrofuran; ethanol / 1.) 0 deg C, 10 min, 2.) RT, overnight 5: 99 percent / ceric ammonium nitrate / H2O; acetonitrile / 0.5 h / Ambient temperature View Scheme

1: 94 percent / benzene / 18 h / Heating 2: 1.) NaH / 1.) benzene, reflux, 2 h, 2.) benzene, reflux, overnight 3: 56 percent / pyridine / Ambient temperature 4: 100 percent / CoCl2, NaBH4 / tetrahydrofuran; ethanol / 1.) 0 deg C, 10 min, 2.) RT, overnight 5: 99 percent / ceric ammonium nitrate / H2O; acetonitrile / 0.5 h / Ambient temperature View Scheme

1: 1.) NaH / 1.) benzene, reflux, 2 h, 2.) benzene, reflux, overnight 2: 56 percent / pyridine / Ambient temperature 3: 100 percent / CoCl2, NaBH4 / tetrahydrofuran; ethanol / 1.) 0 deg C, 10 min, 2.) RT, overnight 4: 99 percent / ceric ammonium nitrate / H2O; acetonitrile / 0.5 h / Ambient temperature View Scheme

1: 1.) NaH / 1.) benzene, reflux, 2 h, 2.) benzene, reflux, overnight 2: 56 percent / pyridine / Ambient temperature 3: 100 percent / CoCl2, NaBH4 / tetrahydrofuran; ethanol / 1.) 0 deg C, 10 min, 2.) RT, overnight 4: 99 percent / ceric ammonium nitrate / H2O; acetonitrile / 0.5 h / Ambient temperature View Scheme

1: 100 percent / CoCl2, NaBH4 / tetrahydrofuran; ethanol / 1.) 0 deg C, 10 min, 2.) RT, overnight 2: 99 percent / ceric ammonium nitrate / H2O; acetonitrile / 0.5 h / Ambient temperature View Scheme