Pt/C-catalyzed Selective Hydrogenation of Nitroarenes to N-arylhydroxylamines under Mild Conditions

Graphical Herein, we report a highly efficient synthesis of N -arylhydroxylamines through controllable hydrogenation of nitroarenes using hydrazine hydrate as a hydrogen donor over Pt/C catalyst at a low temperature (30 °C). The synthesis of N -arylhydroxylamines through the in-situ hydrogenation of nitroarenes over commercial Pt/C catalyst was investigated. The effects of various reaction conditions including hydrogen donor, solvent, catalyst dosage, temperature and reaction time on the selective hydrogenation of nitrobenzene (NB) to N -phenylhydroxylamine (PHA) were systematically investigated. The results showed that the yield of N -phenylhydroxylamine reached 87.2 % using hydrazine hydrate as hydrogen donor in N,N -dimethylformamide solvent at 30 °C for 60 min. And the catalyst showed no obvious activity loss after a 6-times recycle. Meanwhile, the developed methodology can also transform a range of nitroarenes to the corresponding N -arylhydroxylamines in excellent yields (74–99 %).