Aerobic dehydrogenation of cyclohexanone to phenol catalyzed by Pd(TFA)2/2-dimethylaminopyridine: Evidence for the role of Pd nanoparticles

Doris Pun, Tianning Diao, Shannon S. Stahl

Research output: Contribution to journalArticle

Abstract

We have carried out a mechanistic investigation of aerobic dehydrogenation of cyclohexanones and cyclohexenones to phenols with a Pd(TFA) 2/2-dimethylaminopyridine catalyst system. Numerous experimental methods, including kinetic studies, filtration tests, Hg poisoning experiments, transmission electron microscopy, and dynamic light scattering, provide compelling evidence that the initial PdII catalyst mediates the first dehydrogenation of cyclohexanone to cyclohexenone, after which it evolves into soluble Pd nanoparticles that retain catalytic activity. This nanoparticle formation and stabilization is facilitated by each of the components in the catalytic reaction, including the ligand, TsOH, DMSO, substrate, and cyclohexenone intermediate.

Original languageEnglish (US)
Pages (from-to)8213-8221
Number of pages9
JournalJournal of the American Chemical Society
Volume135
Issue number22
DOIs
StatePublished - Jun 5 2013

Fingerprint

Dehydrogenation
Phenol
Nanoparticles
Phenols
Cyclohexanones
Catalysts
Dynamic light scattering
Dimethyl Sulfoxide
Transmission Electron Microscopy
Poisoning
Catalyst activity
Stabilization
Ligands
Transmission electron microscopy
Kinetics
Substrates
Experiments
cyclohexanone
Dynamic Light Scattering

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Aerobic dehydrogenation of cyclohexanone to phenol catalyzed by Pd(TFA)2/2-dimethylaminopyridine : Evidence for the role of Pd nanoparticles. / Pun, Doris; Diao, Tianning; Stahl, Shannon S.

In: Journal of the American Chemical Society, Vol. 135, No. 22, 05.06.2013, p. 8213-8221.

Research output: Contribution to journalArticle

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