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

ChemSusChem
Saumya DabralCarsten Bolm

Abstract

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.

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Citations

Mar 3, 2018·Organic & Biomolecular Chemistry·Ciaran W LahiveNicholas J Westwood
Jul 11, 2018·ChemSusChem·Jian Zhang
Sep 15, 2017·Beilstein Journal of Organic Chemistry·Ulla WeißbachJosé G Hernández
May 26, 2020·ChemSusChem·Xiaojun ShenBuxing Han
May 8, 2020·Chemistry : a European Journal·Nicholas James WestwoodIsabella Panovic
Apr 10, 2018·Chemical Science·Haiwei GuoNicholas J Westwood
Oct 20, 2018·Biotechnology for Biofuels·Lars RegesteinJochen Büchs
Aug 23, 2019·Beilstein Journal of Organic Chemistry·Andrea PorchedduEvelina Colacino
Jul 6, 2018·Topics in Current Chemistry·Thijs VangeelBert F Sels
Dec 11, 2019·Advanced Materials·Min Wang, Feng Wang
Nov 21, 2018·International Journal of Biological Macromolecules·Mónica R C FernandesEmiel J M Hensen
Aug 9, 2018·The Journal of Organic Chemistry·Xuan LiYuetao Zhang
Oct 2, 2020·Organic Letters·Cheng YangCorey R J Stephenson

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