Selective ruthenium-catalyzed oxidation of lignin diol model compounds and lignin was accomplished by a transfer hydrogenation methodology. The developed procedure allows us to selectively oxidize benzylic secondary alcohols in model diols and spruce milled wood lignin in the presence of a commercially available Shvo catalyst under aerobic conditions. Six ketoalcohols were obtained in 70–92% yields from the model compounds, which also included lignin monomers containing 5-5′ and β-O-4 linkages. The developed method can be used as an intermediate step for the introduction of new functional groups into lignin-type structures and lignin to allow their further modifications.