C-C or C-O bond cleavage in a phenolic lignin model compound: selectivity depends on vanadium catalyst

The aerobic oxidation of a phenolic lignin model compound with a vanadium catalyst results in the oxidative cleavage of the C-C bond between the aryl ring and the adjacent hydroxy-substituted carbon atom. Labeling experiments indicate key mechanistic differences to a previously reported related C-O bond cleavage reaction. The selectivity in C-C versus C-O bond cleavage depends on the choice of the vanadium catalyst.