Mixed Phosphite/N-Heterocyclic Carbene Complexes: Synthesis, Characterization and Catalytic Studies

Olivier Diebolt, Vaclav Jurcik, Rosenildo Correa da Costa, Pierre Braunstein, Luigi Cavallo, Steven Patrick Nolan, Alexandra M. Z. Slawin, Catherine S. J. Cazin

Research output: Contribution to journalArticlepeer-review

81 Citations (Scopus)

Abstract

A series of mixed P(OR)(3)/NHC Pd complexes was synthesized and fully characterized. The steric properties of both types of ligands were computationally determined using X-ray data. These structural studies clearly show that N-heterocyclic carbenes modulate their bulkiness with respect to the steric requirements of the coligands. Catalytic studies were performed using this new class of complexes for the Suzuki-Miyaura reaction. It was found that alkoxide or hydroxide bases and/or alcohols were necessary to achieve good catalytic activity. Mechanistic studies were undertaken in order to gain insights into the role of alkoxide groups. These studies suggest that alcohols or alkoxide groups play a major role in the activation of the precatalyst to generate the catalytically active species. Catalytic studies proved these systems to be efficient using 0.1 mol % of Pd loading for the coupling of aryl, benzyl, and heterocyclic chlorides with boronic acids.

Original languageEnglish
Pages (from-to)1443-1450
Number of pages8
JournalOrganometallics
Volume29
Issue number6
DOIs
Publication statusPublished - 22 Mar 2010

Keywords

  • CROSS-COUPLING REACTIONS
  • TEMPERATURE SUZUKI-MIYAURA
  • HINDERED ARYL CHLORIDES
  • ROOM-TEMPERATURE
  • TRIARYLPHOSPHITE COMPLEXES
  • PALLADIUM CATALYSTS
  • BUCHWALD-HARTWIG
  • NHC
  • LIGANDS
  • ELECTROPHILES

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