1: sodium tetrahydroborate / water; tetrahydrofuran / 20 °C 2: hydrogenchloride / ethanol / 3 h / 60 °C 3: sulfur trioxide pyridine complex; triethylamine / dimethyl sulfoxide; dichloromethane / 20 °C 4: formic acid; [Ir(phenylpyridine(-1H))2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6); N-ethyl-N,N-diisopropylamine / acetonitrile / 24 h / 20 °C / |Irradiation View Scheme

1: sodium tetrahydroborate / water; tetrahydrofuran / 20 °C 2: silica gel; C26H51N2O2(1+)*BF4(1-) / dichloromethane / 15 h / 20 °C 3: formic acid; [Ir(phenylpyridine(-1H))2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6); N-ethyl-N,N-diisopropylamine / acetonitrile / 48 h / 20 °C / |Irradiation View Scheme

1: sodium tetrahydroborate / water; tetrahydrofuran / 20 °C 2: hydrogenchloride / ethanol / 3 h / 60 °C 3: sulfur trioxide pyridine complex; triethylamine / dimethyl sulfoxide; dichloromethane / 20 °C 4: formic acid; [Ir(phenylpyridine(-1H))2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6); N-ethyl-N,N-diisopropylamine / acetonitrile / 24 h / 20 °C / |Irradiation View Scheme

1.1: sodium tetrahydroborate / tetrahydrofuran; water 2.1: 4-acetylamino 2,2,6,6-tetramethylpiperidin-N-oxyl; oxygen / water; acetonitrile / |Sealed tube 2.2: 9 h / 45 °C 3.1: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; methanol / 10 h / 50 °C View Scheme

1: sodium tetrahydroborate / water; tetrahydrofuran / 20 °C 2: silica gel; C26H51N2O2(1+)*BF4(1-) / dichloromethane / 15 h / 20 °C 3: formic acid; [Ir(phenylpyridine(-1H))2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6); N-ethyl-N,N-diisopropylamine / acetonitrile / 48 h / 20 °C / |Irradiation View Scheme

sodium tetrahydroborate in tetrahydrofuran; water T=20°C;

1: sodium tetrahydroborate / tetrahydrofuran; water 2: 4-acetylamino 2,2,6,6-tetramethylpiperidin-N-oxyl; nitric acid; sodium nitrite / water; acetic acid / 12 h / 20 °C / 760.05 Torr View Scheme