The scope of an existing method for the ruthenium-catalyzed oxidation of silyl ethers to silyl esters was expanded to include a range of para-substituted benzyl substrates. Oxidation in the original CCl4/H2O biphasic solvent system formed the analogous silyl ester as the major product along with the carboxylic acid, aldehyde, and acid anhydride as observed by 1H NMR. Replacing CCl4 with ethyl acetate as the organic solvent resulted in higher percent yields of the silyl ester within a shorter time. Other reaction conditions including temperature, reoxidant ratio, and catalyst ratio were also optimized. Reproducibility with smaller amounts of catalyst was achieved using aqueous stock solutions of RuCl3. Currently, workup conditions are being optimized to obtain isolated yields of the benzyl silyl esters.

Ruthenium-catalyzed oxidation of benzyl silyl ethers to silyl esters

ACS Spring 2022

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