Cleavage of C-O bonds in lignin model compounds catalyzed by methyldioxorhenium in homogeneous phase

Reentje G. Harms; Iulius I.E. Markovits; Markus Drees; H. C.Mult Wolfgang A. Herrmann; Mirza Cokoja; Fritz E. Kühn

doi:10.1002/cssc.201300918

Cleavage of C-O bonds in lignin model compounds catalyzed by methyldioxorhenium in homogeneous phase

Reentje G. Harms, Iulius I.E. Markovits, Markus Drees, H. C.Mult Wolfgang A. Herrmann, Mirza Cokoja, Fritz E. Kühn

Technical University of Munich

Research output: Contribution to journal › Article › peer-review

71 Scopus citations

Abstract

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, 17O- and 2H-isotope labeling experiments, DFT calculations, and several spectroscopic studies, a reaction mechanism is proposed.

Original language	English
Pages (from-to)	429-434
Number of pages	6
Journal	ChemSusChem
Volume	7
Issue number	2
DOIs	https://doi.org/10.1002/cssc.201300918
State	Published - Feb 2014

Keywords

C-O bond cleavage
homogeneous catalysis
lignin
renewable resources
rhenium

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/cssc.201300918

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title = "Cleavage of C-O bonds in lignin model compounds catalyzed by methyldioxorhenium in homogeneous phase",

abstract = "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, 17O- and 2H-isotope labeling experiments, DFT calculations, and several spectroscopic studies, a reaction mechanism is proposed.",

keywords = "C-O bond cleavage, homogeneous catalysis, lignin, renewable resources, rhenium",

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AU - Harms, Reentje G.

AU - Markovits, Iulius I.E.

AU - Drees, Markus

AU - Herrmann, H. C.Mult Wolfgang A.

AU - Cokoja, Mirza

AU - Kühn, Fritz E.

PY - 2014/2

Y1 - 2014/2

N2 - 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, 17O- and 2H-isotope labeling experiments, DFT calculations, and several spectroscopic studies, a reaction mechanism is proposed.

AB - 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, 17O- and 2H-isotope labeling experiments, DFT calculations, and several spectroscopic studies, a reaction mechanism is proposed.

KW - C-O bond cleavage

KW - homogeneous catalysis

KW - lignin

KW - renewable resources

KW - rhenium

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Cleavage of C-O bonds in lignin model compounds catalyzed by methyldioxorhenium in homogeneous phase

Abstract

Keywords

UN SDGs

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