The oxidation of alcohols into their corresponding carbonyl compounds represents a fundamentally important functional group transformation and occupies a prominent position in modern synthetic organic chemistry. During the course of our recent investigation on new generation of dihydroxylation catalysts, we had had the pleasure of preparing DMAP-derived benzylic alcohol 1 and desired to use its sodium alkoxide ion for an intended nucleophilic substitution event. However, upon treatment of 1 with NaH in THF at room temperature for 10hs, it was found that the reaction surprisingly gave ketone 2 cleanly in 95% isolated yield. Intrigued by this interesting transformation, we embarked on a program investigating the sodium hydride promoted oxidation. A novel tandem radical formation-collapse mechanism has been determined for these reactivities.

New wines in a very old bottle: Reactivities of a simplest oxidant NaH/Air

241st National Meeting (2011)

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