Toward the oxidative deconstruction of lignin: Oxidation of β-1 and β-5 linkages

Zhen Fang, Mark S. Meier

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

There have been numerous reports on methods for the oxidative cleavage of β-O-4 linkages in lignin model compounds, but relatively few reports of how those methods affect other linkages that are present in lignin. We have investigated the effect of several of these oxidation methods on the β-1 and the β-5 lignin linkages, using four β-1 and β-5 model compounds. We observed that direct oxidative cleavage of C-C bonds occurs in metal-catalyzed TEMPO oxidation systems and with iron porphyrin oxidations, neither of which had we observed in similar oxidations on β-O-4 models. The β-5 linkage proved to be largely resistant to all of these oxidative systems, but the dihydrofuran ring in the β-5 model 3 was opened when treated with KMnO4 at elevated temperature. Most promising was the oxidation of 2 with DDQ, which produced the benzylic ketone in high yield (84%), as it does in reactions with β-O-4 models. This reaction exhibits selectivity for the benzylic position as well as compatibility with phenols, characteristics that are highly desirable for a two-step, benzylic oxidation/Baeyer-Villiger route for cleavage of lignin.

Original languageEnglish
Pages (from-to)2330-2341
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number13
DOIs
StatePublished - 2018

Bibliographical note

Publisher Copyright:
© 2018 The Royal Society of Chemistry.

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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