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Amongst the known procedures for this transformation is the notably mild method utilizing catalytic tetra-N-propylammonium perruthenate (TPAP), and N-methylmorpholine-N-oxide (NMO) as a stoichiometric cooxidant.[14] This procedure was shown to convert a small number of simple benzylamines successfully into the corresponding imines. Ruthenium catalysis is also involved in a more recent procedure in which oxygen is employed as the stoichiometric cooxidant.[13] Alternative transition-metal-based protocols include employing expensive cobalt Schiff base complexes,[18] a copper bromide-lithium tert-butoxide combination,[15] manganese salen and iron porphyrins,[16] and manganese dioxide in refluxing benzene,[23] but again the substrate range reported was rather limited. Oxidations with diphenylselenium bis(trifluoroacetate)[21] or Fremy's salt[22] have been explored in the oxidation of simple tetrahydroisoquinoline systems. Furthermore, other methods employing Swern conditions,[19] di-tert-butyliminoxyl radicals,[20] iodosobenzene[16] or hypervalent tert-butylperoxyiodanes[12] for accomplishing this reaction can justifiably be described as restricted with regard to their scope and efficiency.
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