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In complexation reactions, metal cations are the electron pair acceptors, and the ligands are the electron pair donors. The stability of the metal complexes depends primarily on the complexing ability of the central metal ion and the nature of the ligands. Generally, the complexing ability of the metal ion depends on the size and charge of the ion. As the metal ion size increases, the stability of the metal complexes decreases, provided that the valency of the metal ion and the ligands remain...
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Anionic Palladium(0) and Palladium(II) Ate Complexes.

Marlene Kolter1, Katharina Böck2, Konstantin Karaghiosoff2

  • 1Institut für Organische und Biomolekulare Chemie, Universität Göttingen, Tammannstrasse 2, 37077, Göttingen, Germany.

Angewandte Chemie (International Ed. in English)
|August 18, 2017
PubMed
Summary

Electron-poor palladium catalysts form anionic ate complexes with bromide ions, a finding supported by mass spectrometry and NMR. Electron-rich catalysts show less tendency to form these important Heck reaction intermediates.

Keywords:
cross-couplingmass spectrometrypalladiumreactive intermediatessalt effects

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Area of Science:

  • Organometallic Chemistry
  • Catalysis Research

Background:

  • Palladium ate complexes are crucial intermediates in Heck and cross-coupling reactions.
  • Characterization of these intermediates at the molecular level has been challenging.

Purpose of the Study:

  • To characterize palladium ate complexes using advanced spectroscopic and conductivity techniques.
  • To investigate the influence of catalyst electronic properties on ate complex formation.

Main Methods:

  • Electrospray-ionization mass spectrometry (ESI-MS)
  • Electrical conductivity measurements
  • Nuclear Magnetic Resonance (NMR) spectroscopy

Main Results:

  • An electron-poor palladium catalyst, [L3Pd], readily forms an anionic, zero-valent ate complex, [L3PdBr]-, upon reaction with bromide ions.
  • Electron-rich palladium catalysts exhibit a reduced tendency for ate complex formation.
  • A Pd(II) ate complex, [L2Pd(Ar)I2]-, was observed when combining the catalyst with LiI and an aryl iodide substrate.

Conclusions:

  • The study provides molecular-level characterization of palladium ate complexes.
  • Catalyst electronic properties significantly influence the formation of these key reaction intermediates.