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Cleavage of CO Bonds in Lignin Model Compounds Catalyzed by Methyldioxorhenium in Homogeneous Phase
Author(s) -
Harms Reentje G.,
Markovits Iulius I. E.,
Drees Markus,
Herrmann h.c. mult. Wolfgang A.,
Cokoja Mirza,
Kühn Fritz E.
Publication year - 2014
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.201300918
Subject(s) - lignin , homogeneous , catalysis , cleavage (geology) , chemistry , bond cleavage , homogeneous catalysis , phase (matter) , stereochemistry , organic chemistry , computational chemistry , combinatorial chemistry , polymer chemistry , materials science , thermodynamics , physics , fracture (geology) , composite material
Methyldioxorhenium (MDO)‐catalyzed CO 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.