A bifunctional approach towards the mild oxidation of organic halides: 2-dimethylamino-N,N-dimethylaniline N-oxide

The titled reagent incorporates an oxygen-centred nucleophile and a basic moiety—in a suitably mutual orientation—in the same molecule. It oxidises various primary benzylic bromides to the corresponding aromatic aldehydes under relatively mild conditions (MeCN/rt–50°C/6–24 h) in high yields (83–97%), and is thus a useful alternative to the Kornblum procedure.