Formation and propagation of well-defined Pd nanoparticles (PdNPs) during C–H bond functionalization of heteroarenes: are nanoparticles a moribund form of Pd or an active catalytic species?

Christoph G. Baumann, Sara De Ornellas, Jonathan P. Reeds, Thomas E. Storr, Thomas J. Williams, Ian J.S. Fairlamb

Research output: Contribution to journalArticlepeer-review

46 Citations (Scopus)

Abstract

Examination of a series of C–H bond functionalization reactions of heteroarenes (e.g., indole, benzoxazole, benzthiazole, benzimidazole and purine derivatives) mediated by Pd(OAc)2, a commonly used C–H bond functionalization catalyst, reveals that well-defined Pd nanoparticles (PdNPs) are rapidly formed under working catalyst conditions. The PdNPs can be characterized ex situ after entrapment in a polymer matrix (polyvinylpyrrolidinone, PVP). Independently synthesized Pd(PVP)NPs are catalytically competent species, exhibiting catalyst activity commensurate with Pd(OAc)2 in several C–H bond functionalization reactions. Across a range of reactions, Pd concentration is a common variable, which can be linked to the propagation of PdNPs under working catalytic conditions using polar solvents like DMF, DMSO and acetic acid.
Original languageEnglish
Pages (from-to)6174-6187
Number of pages14
JournalTetrahedron
Volume70
Issue number36
Early online date6 Jun 2014
DOIs
Publication statusPublished - 9 Sep 2014

Keywords

  • Palladium
  • Nanoparticles
  • Cross-coupling
  • Catalysis

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