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

ASJC Scopus subject areas

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

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