Heterogeneous Catalysis as an Efficient Tool for Selective Hydrogenation of Oximes to Amines and Hydroxylamines

The synthesis of many biologically active compounds is not complete without transforming the carbonyl group into an amino group, carried out by the reaction of nucleophilic substitution with hydroxylamine at the carbonyl carbon atom and further reduction of the C–N and N–O bonds. This method eliminates nitrating agents that exhibit oxidizing properties and may cause undesirable effects on other structural fragments of complex molecules. Selective hydrogenation of oximes over heterogeneous catalysts is still one of the most useful and challenging reactions in synthetic organic chemistry to obtain amines and hydroxylamines since the 1920s when the Adam’s catalyst was first used for this reaction. In this review, we focused on the application of heterogeneous catalysts for the hydrogenation of oximes in relation to the methods applied for pharmaceutical synthesis.