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It is well known that secondary amines carrying C-H bonds in α to N atom (R-NH-CHR2) undergo oxidation by ruthenium-based catalysts (including ruthenium tetroxide) to yield imines (R-N=CR2), by a formal 1,2-dehydrogenation process. By analogy with the oxidation of secondary alcohols, the advanced mechanism involves two distinct hydrogen-transfer processes: the first for the N-H proton, the second for the C-H one (Scheme 1). RuO4 acts as a two-electron oxidant. At their turn, imines are reactive compounds. For instance, if the oxidation is performed in the presence of NaCN, αaminonitriles are formed from imines and HCN (generated in situ). In the absence of cyanide, nucleophilic addition of water leads to a hemiaminal, which can be split into a mixture of primary amine and aldehyde and/or oxidized towards the corresponding amide.

Homolytic pathway for the RuO4-oxidation of amines