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Reduction of nitro compounds

Recent Literature


N
-Alkylaminobenzenes were prepared in a simple and efficient one-pot synthesis by reduction of nitrobenzenes followed by reductive amination with decaborane (B10H14) in the presence of 10% Pd/C.
J. W. Bae, Y. J. Cho, S. H. Lee, C.-O. M. Yoon, C. M. Yoon, Chem. Commun., 2000, 1857-1858.


Palladium-catalyzed reduction of aromatic nitro groups to amines can be accomplished in high yield, with wide functional group tolerance and short reaction times at r.t. using aqueous potassium fluoride and polymethylhydrosiloxane (PMHS) for aromatic nitro groups. Aliphatic nitro compounds are reduced to the corresponding hydroxylamines using triethylsilane instead of PMHS/KF.
R. J. Rahaim, R. E. Maleczka (Jr.), Org. Lett., 2005, 7, 5087-5090.


A generally applicable method for the introduction of gaseous hydrogen into a sealed reaction system under microwave irradiation allows the hydrogenation of various substrates in short reaction times with moderate temperatures between 80 °C and 100 °C with 50 psi of hydrogen.
G. S. Vanier, Synlett, 2007, 131-135.


Poly(ethylene glycol) (PEG) (400) has been found to be a superior solvent over ionic liquids by severalfold in promoting the hydrogenation of various functional groups using Adams' catalyst. Both the catalyst and PEG were recycled efficiently over 10 runs without loss of activity, and without substrate cross contamination.
S. Chandrasekhar, S. Y. Prakash, C. L. Rao, J. Org. Chem., 2006, 71, 2196-2199.


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.


R. J. Rahaim, R. E. Maleczka, Jr., Org. Lett., 2005, 7, 5087-5090.


A mild and efficient electron-transfer method for the chemoselective reduction of aromatic nitro groups using samarium(0) metal in the presence of a catalytic amount of 1,1'-dioctyl-4,4'-bipyridinium dibromide gives aromatic amines in good yield with selectivity over a number of other functional and protecting groups.
C. Yu, B. Liu, L. Hu, J. Org. Chem., 2001, 66, 919-924.