Cleavage of CO Bonds in Lignin Model Compounds Catalyzed by Methyldioxorhenium in Homogeneous Phase

Methyldioxorhenium (MDO)‐catalyzed CO bond cleavage of a variety of lignin β‐O‐4‐model compounds yields phenolic and aldehydic compounds in homogeneous phase under mild reaction conditions. MDO is in situ generated by reduction of methyltrioxorhenium (MTO) and is remarkably stable under the applied...

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Bibliographic Details
Published in:ChemSusChem 2014-02, Vol.7 (2), p.429-434
Main Authors: Harms, Reentje G., Markovits, Iulius I. E., Drees, Markus, Herrmann, h.c. mult. Wolfgang A., Cokoja, Mirza, Kühn, Fritz E.
Format: Article
Language:English
Subjects:
Carbon - chemistry
Catalysis
CO bond cleavage
homogeneous catalysis
lignin
Lignin - chemistry
Organometallic Compounds - chemistry
Oxygen - chemistry
renewable resources
rhenium
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Summary:Methyldioxorhenium (MDO)‐catalyzed CO bond cleavage of a variety of lignin β‐O‐4‐model compounds yields phenolic and aldehydic compounds in homogeneous phase under mild reaction conditions. MDO is in situ generated by reduction of methyltrioxorhenium (MTO) and is remarkably stable under the applied reaction conditions allowing its reuse for least five times without significant activity loss. Based on the observed and isolated intermediates, 17 O‐ and 2 H‐isotope labeling experiments, DFT calculations, and several spectroscopic studies, a reaction mechanism is proposed. CO Re business: Methyldioxorhenium (MDO) is an efficient catalyst for the CO bond cleavage of various aryl ethers in homogeneous phase; a reaction that serves as a model towards the depolymerization of lignin and its β‐O‐4 bonds. The mechanism of the reaction is elucidated by means of NMR spectroscopy, GC, and DFT studies.
ISSN:1864-5631
1864-564X
DOI:10.1002/cssc.201300918