A stable nitroxyl radical serving as a catalytic oxidant. Applied in catalytic oxidation of nerol to neral,1 catalytic oxidation of primary and secondary alcohols to aldehydes and ketones,2 catalytic oxidation of 1,2-diols to α-hydroxy ketones or α-diketones,3 aerobic oxidation of benzylic alcohols in water,4 catalytic oxidative amidation-diketonization reaction of terminal alkynes to give α-ketoamides,5 mono-oxidation of unprotected glycosides in combination with trichloroisocyanuric acid to afford dialdo-glycosides,6 oxidative conversion of primary amines to the corresponding nitriles,7 oxidatively cleavage of benzylic ethers to give the corresponding aromatic aldehydes and alcohols,8 oxidative rearrangement of tertiary allylic alcohols to β-substituted α,β-unsaturated carbonyl compounds,9 and cross coupling of ortho-substituted aryl Grignard reagents with alkynyl Grignard reagents.10
Reference
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10. Org. Lett. 2010, 12, 3878.