Organocatalytic Chemoselective Primary Alcohol Oxidation and Subsequent Cleavage of Lignin Model Compounds and Lignin.

Saumya Dabral, José G Hernández, Paul C J Kamer, Carsten Bolm

ChemSusChem 2017 Jul 10

filter terms:

A one-pot two-step degradation of lignin β-O-4 model compounds initiated by preferred oxidation of the primary over the secondary hydroxyl groups with a TEMPO/DAIB system has been developed [TEMPO=2,2,6,6-tetramethylpiperidine-N-oxyl, DAIB=(diacetoxy)iodobenzene]. The oxidised products are then cleaved by proline-catalysed retro-aldol reactions. This degradation methodology produces simple aromatics in good yields from lignin model compounds at room temperature with an extension to organosolv beech-wood lignin (L1) resulting in known cleavage products. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Saumya Dabral, José G Hernández, Paul C J Kamer, Carsten Bolm. Organocatalytic Chemoselective Primary Alcohol Oxidation and Subsequent Cleavage of Lignin Model Compounds and Lignin. ChemSusChem. 2017 Jul 10;10(13):2707-2713