3-chloro-benzenecarboperoxoic acid in dichloromethane T=0°C; 48 h;

bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate; 6-diphenylphosphinomethyl-3-methyl-2-aminopyridine in toluene T=150°C; 1 h; Inert atmosphere;

1: sulfuric acid / 3 h / 60 °C / Inert atmosphere 2: caesium carbonate; triphenylphosphine; palladium dichloride / tetrahydrofuran; water / 22 h / 85 °C / sealed tube; Inert atmosphere 3: bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate; 6-diphenylphosphinomethyl-3-methyl-2-aminopyridine / toluene / 1 h / 150 °C / Inert atmosphere View Scheme

1: caesium carbonate; triphenylphosphine; palladium dichloride / tetrahydrofuran; water / 22 h / 85 °C / sealed tube; Inert atmosphere 2: bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate; 6-diphenylphosphinomethyl-3-methyl-2-aminopyridine / toluene / 1 h / 150 °C / Inert atmosphere View Scheme

1: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / benzene / 16 h / Reflux; Inert atmosphere 2: sulfuric acid / 3 h / 60 °C / Inert atmosphere 3: caesium carbonate; triphenylphosphine; palladium dichloride / tetrahydrofuran; water / 22 h / 85 °C / sealed tube; Inert atmosphere 4: bis(1,5-cyclooctadiene)-rhodium(I) tetrafluoroborate; 6-diphenylphosphinomethyl-3-methyl-2-aminopyridine / toluene / 1 h / 150 °C / Inert atmosphere View Scheme

chromium(VI) oxide; acetic acid

1: With sulfuric acid; nitric acid 2: With chromium(VI) oxide; acetic acid Further stages.;

1: sodium borohydride / methanol / 3 h / Ambient temperature 2: 82 percent / p-Toluenesulfonic acid / benzene / 3 h / Heating View Scheme

1: NaBH4 / methanol 2: TsOH / toluene View Scheme

1: sodium borohydride / methanol / 3 h / Ambient temperature 2: 82 percent / p-Toluenesulfonic acid / benzene / 3 h / Heating 3: sulfurated sodium borohydride / tetrahydrofuran / 16 h / Ambient temperature 4: 1.) NaNO2, 20percent H2SO4, 2.) KI / 1.) H2O, 0 deg C, 12 min, 2.) H2O, flask in aluminum foil, 30 min stirring View Scheme