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Organocatalytic Chemoselective Primary Alcohol Oxidation and Subsequent Cleavage of Lignin Model Compounds and Lignin
Author(s) -
Dabral Saumya,
Hernández José G.,
Kamer Paul C. J.,
Bolm Carsten
Publication year - 2017
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201700703
Subject(s) - lignin , chemistry , primary (astronomy) , alcohol , organic chemistry , alcohol oxidation , cleavage (geology) , catalysis , primary alcohol , organocatalysis , coniferyl alcohol , materials science , enantioselective synthesis , physics , astronomy , fracture (geology) , composite material
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.