Lignin is an abundantbiopolymer with aromatic subunits in itsbackbone, and depolymerizationof this polymer could provide a source of valuable aromatic chemicals. The beta-O-4 unit, which features secondary benzylic and primary aliphatic alcohols (Figure 1), is the most prevalent linkage in the structure of lignin, and its cleavage provides high yields of aromatic monomers. The hydroxyl functional groups within this linkage are susceptible to oxidation, and their controlled oxidationprovides the basis for lignin depolymerization.[i]We have shown previously that the benzylic alcohol in lignin undergoes selective oxidation with an aminoxyl/NOxcocatalyst system under aerobic conditions. Subsequent treatment of the oxidized lignin with formic acid affords high yields of aromatic monomers.[ii]This talk will describe a complementary electrochemical method for selective oxidation of the benzylic alcohols in lignin. N-Hydroxyimide derivatives undergo facile proton coupled electron transfer at electrode surfaces to generate an imidoxyl radical that promotes efficient hydrogen atom transfer from the of benzylic hydroxyl groups.[iii]Our advances in the use of electrochemically generated imidoxyl radicals for chemoselective oxidation of hydroxyl groups in the structure of lignin will be presented. Benzylic alcohol oxidation proceeds efficiently to the corresponding ketones using imidoxyl radicals as electrocatalyst in water/acetone as solvent and with acetic acid/acetate as buffer and supporting electrolyte. Treatment of the oxidized lignin with formic acid affords more than 30 wt% of monomeric aromatic compounds. [i]. Li,C.; Zhao,X.; Wang,A.; Huber, G.W.; Zhang T. Chem. Rev. 2015,115, 11559. [ii]. Rahimi, A.; Ulbrich, A.; Coon, J. J.; Stahl S. S.Nature 2014, 515, 249. [iii]. Nutting, J. E.; Rafiee, M. R.; Stahl, S. S. Chem. Rev. 2018, 118, 4834. Figure 1. Imidoxyl catalyzed electrochemical oxidation of lignin followed by formic acid catalyzed depolymerization. Figure 1