Highly effective C-C bond cleavage of lignin model compounds

A highly effective method is developed for the C-C bond cleavage of lignin model compounds. The inert C-alpha-C-beta or C-alpha-C-phenyl bond of oxidized lignin model compounds was successfully converted to an active ester bond through the classic organic name reaction, Baeyer-Villiger (BV) oxidation, and thus acetal esters and aryl esters were produced in high yields (up to 99%) at room temperature. Next, K2CO3 catalyzed the alcoholysis of the resulting ester products at 45 degrees C, affording various useful chemical platforms in excellent yields (up to 99%), such as phenols and multifunctional esters. This method uses commercially available reagents, is transition-metal free and simple, but highly effective, and involves mild reaction conditions.