Lignol cleavage by Pd/C under mild conditions and without hydrogen: A role for benzylic C=H activation?

Xiaoyuan Zhou, Joyee Mitra, Thomas B. Rauchfuss

Research output: Contribution to journalArticlepeer-review

Abstract

The cleavage of C=O bonds in lignin model compounds without hydrogen was developed using the commercially available Pd/C. Hydrogen donor solvents are helpful for this reaction through transfer hydrogenation, but not necessary. A redox neutral process that utilizes the internal hydrogen source for the cleavage is also possible. An initial mechanistic study indicates that the β-benzylic-H atom in the substrate plays a critical role and that the present system undergoes a process different from previous reports. Cleavage within: The selective cleavage of β-O-4 bond linkage in lignin has received great attention. We developed a method using the commercially available heterogeneous catalyst, Pd/C, to cleave the C=O bond in β-O-4 linkage model compound without hydrogen. A mechanistic study shows that the present catalytic system undergoes a process different from previous reports, in which the β-benzylic-H atom in the substrates plays a critical role.

Original languageEnglish (US)
Pages (from-to)1623-1626
Number of pages4
JournalChemSusChem
Volume7
Issue number6
DOIs
StatePublished - Jun 2014

Keywords

  • biomass
  • heterogeneous catalysis
  • lignin
  • palladium
  • reaction mechanisms

ASJC Scopus subject areas

  • Energy(all)
  • Environmental Chemistry
  • Materials Science(all)
  • Chemical Engineering(all)

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