Chemoselective hydrogenation of aromatic nitro compounds in the presence of homogeneous Pd based catalysts

The chemoselective reduction of aromatic nitro compounds to amine derivatives was easily performed with remarkable yields under ultrasonic conditions in a H2O/MeOH mixture (v/v = 1/4). In this process, commercially available BINAP.PdCl2 and NaBH4 were used as homogenous catalysts and the hydrogen source, respectively. The developed method has a high economic value and can be adapted to the industry. A variety of nitroarene derivatives were reacted by undergoing the BINAP.PdCl2 catalyzed reduction reaction. All nitroarenes were selectively hydrogenated to aromatic primary amines with quantitative yields in 15 min. The obtained primary amines were determined by 1H and 13C nuclear magnetic resonance spectroscopy.

Automated summary

The chemoselective reduction of aromatic nitro compounds to amine derivatives was successfully achieved using commercially available BINAP.PdCl2 and NaBH4 as catalysts and hydrogen source in a H2O/MeOH mixture under ultrasonic conditions. The developed method exhibits high economic value and applicability for industrial settings, allowing for the selective hydrogenation of various nitroarene derivatives to aromatic primary amines with quantitative yields in a short period of time. The primary amines obtained were confirmed by 1H and 13C nuclear magnetic resonance spectroscopy.