Isolation of Functionalized Phenolic Monomers through Selective Oxidation and CO Bond Cleavage of the β-O-4 Linkages in Lignin

Functionalized phenolic monomers have been generated and isolated from an organosolv lignin through a two‐step depolymerization process. Chemoselective catalytic oxidation of β‐O‐4 linkages promoted by the DDQ/tBuONO/O2 system was achieved in model compounds, including polymeric models and in real l...

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Veröffentlicht in:Angewandte Chemie International Edition 2015-01, Vol.54 (1), p.258-262
Hauptverfasser: Lancefield, Christopher S., Ojo, O. Stephen, Tran, Fanny, Westwood, Nicholas J.
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Sprache:eng
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Zusammenfassung:Functionalized phenolic monomers have been generated and isolated from an organosolv lignin through a two‐step depolymerization process. Chemoselective catalytic oxidation of β‐O‐4 linkages promoted by the DDQ/tBuONO/O2 system was achieved in model compounds, including polymeric models and in real lignin. The oxidized β‐O‐4 linkages were then cleaved on reaction with zinc. Compared to many existing methods, this protocol, which can be achieved in one pot, is highly selective, giving rise to a simple mixture of products that can be readily purified to give pure compounds. The functionality present in these products makes them potentially valuable building blocks. Lignin depolymerization: A two‐step approach comprising the selective aerobic oxidation of the benzyl alcohols of lignin using DDQ/tBuONO/O2 followed by cleavage of the β‐O‐4 linkages of lignin through treatment with metallic zinc affords functionalized small molecules. These products will be useful building blocks for the preparation of biomass‐derived fine chemicals and materials.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201409408