Alcohol oxidations are generally carried out using hazardous reagents often in stoichiometric amounts such as the Dess-Martin periodinane or the Jones reagents. A new alternative to these methods is a vanadium(V) catalyst, (Me4N)2[V2(O)2(μ-O)2(pinF)2], capable of using the oxygen in air to promote the conversion of activated benzylic and allylic alcohols into their respective aldehydes and ketones. When heated in dimethylacetamide and open to air, this catalyst produces high yields from a variety of benzylic and allylic alcohols. Conversion rates depend highly on the substituents indicating that this catalyst can help carry out highly chemoselective reactions without the need for protecting groups. Further applications include the selective oxidation of various natural products that contain multiple oxidizable alcohol groups. Moreover, this catalyst is bench stable without special protection from moisture or atmospheric oxygen.

Chemoselective air oxidations of alcohols using a vanadium(V) catalyst

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