Chemoselective methods of oxidizing aldehydes to carboxylic acids with oxygen as the oxidant under mild and green conditions are of general interest. A novel vanadium(V) perfluoropinacolate catalyst studied in the present work has been found to selectively oxidize secondary and primary benzylic alcohols to ketones and aldehydes, respectively, and also oxidize benzaldehydes to carboxylic acids at synthetically useful yields. Interestingly, carboxylic acids are not produced in the course of primary alcohol oxidations. All oxidations were achieved with &lt; 5% of the catalyst with ambient air as the terminal oxidant. Importantly, the catalyst proved to be bench stable for up to a year without any special precautions to exclude water or oxygen. To further probe the selectivity and potential synthetic use of the catalyst, a series of oxidations were performed on a range of substrates and various natural products with oxidizable groups.

Evaluating chemoselectivity of a novel vanadium(V) catalyst through oxidation of natural products

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