An efficient Fe/CaCl2 system enables the reduction of nitroarenes and reductive cleavage of azo compounds by catalytic transfer hydrogenation in the presence of sensitive functional groups including halides, carbonyl, aldehyde, acetyl, nitrile, and ester substituents with excellent yields. The simple experimental procedure and easy purification make the protocol advantageous.
S. Chandrappa, T. Vinaya, T. Ramakrishnappa, K. S. Rangappa, Synlett, 2010, 3019-3022.
Vasicine, an abundantly available quinazoline alkaloid from the leaves of Adhatoda vasica, enables an efficient metal- and base-free reduction of nitroarenes to the corresponding anilines in water. The chemoselective method tolerates a wide range of reducible functional groups, such as ketones, nitriles, esters, halogens, and heterocyclic rings. Dinitroarenes are reduced selectively to the corresponding nitroanilines.
S. Sharma, M. Kumar, V. Kumar, N. Kumar, J. Org. Chem., 2014, 79, 9433-9439.
(Ph3P)3RuCl2 is an inexpensive catalyst, that enables a chemoselective reduction of alkyne, ketones, or nitro groups in the presence of Zn/water as a stoichiometric reductant. Depending on the nature of the additive and the temperature, chemoselective reduction of a nitro group in the presence of a ketone or an alkyne was possible.
T. Schabel, C. Belger, B. Plietker, Org. Lett., 2013, 15, 2858-2861.
Several bromo, chloro, iodo and multihalogenated nitroarenes have been selectively reduced with hydrazine hydrate in the presence of Pd/C to give the corresponding halogenated anilines in good yield. Using microwave irradiation at elevated temperature and pressure, dehalogenated products can be isolated.
F. Li, B. Frett, H.-y Li, Synlett, 2014, 25, 1403-1408.
A microwave-assisted, palladium-catalyzed catalytic transfer hydrogenation of different homo- or heteronuclear organic compounds using formate salts as a hydrogen source was performed in ([bmim][PF6]. Essentially pure products could be isolated in moderate to excellent yields by simple liquid-liquid extraction.
H. Berthold, T. Schotten, H. Hönig, Synthesis, 2002, 1607-1610.
i use iron with ammonium chloride in aqueous ethanol or methanol under reflux. very mild method and tolerates many functional groups. Product for me is usually very clean and can be used without purification.
Yes, the method that mentioned by Eugene (using Fe/NH4Cl) in aq.EtOH or MeOH under reflux is effective method for reducing the nitro aromatic coompounds.