Electro-reductive Fragmentation of Oxidized Lignin Models

Lignin provides a potential sustainable source for production of electron-rich aromatic compounds. Recently, electrochemical lignin degradation via an oxidation/reduction sequence under mild conditions has garnered much attention within the lignin community, as electrochemistry simplifies redox reactions and offers an electron source/sink for synthesis without using stoichiometric oxidants or reductants. This paper describes a fundamental approach for the electrochemical fragmentation of the primary connection in native lignin, beta-O-4. Potential-controlled electrolysis enables selective reduction and provides fragmentation products and/or coupling products in isolated yields of 59-92%.