Abstract
One-pot oxidation from primary alcohols to carboxylic acids is one of the most important methods in organic synthesis. With attention to the mechanistic advantage of Merck’s method (cat.2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO)/cat.NaOCl/NaClO2), we have developed an efficient one-pot oxidation using 1-Me-AZADO+X-(oxoammonium salt of 1-methyl-2-azaadamantane N-oxyl) and NaClO2. After that, our research interest was focused on selective oxidation from diols to hydroxy acids. Herein, we report development of a highly active oxidation catalyst for selective oxidation of primary alcohols, 1,5-dimethyl-Nor-AZADO (DMN-AZADO), and DMN-AZADO-catalyzed selective oxidation of diols to hydroxy acids, and also report the chemoselective oxidation of 1,2-diols to α-hydroxy acids together with the one-pot oxidative cleavage from 1,2-diols to one-carbon-shorter carboxylic acids. A mechanistic study suggests that the formation of charge-transfer complex TEMPO-ClO2 is a key for the observed chemoselectivity.
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