Replacement of N-heterocyclic carbenes by N-heterocyclic silylenes at a Pd(0) center: Experiment and theory

Alexander Zeller, Frank Bielert, Peter Haerter, Wolfgang A. Herrmann, Thomas Strassner

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27 Scopus citations

Abstract

Via NMR-spectroscopy the relative reactivity of N-heterocyclic silylenes (NHSi) and carbenes (NHC) was studied. Reaction of sterically crowded bis-N-heterocyclic Pd(0) carbene complexes with free N-heterocyclic silylenes led to complete displacement of the N-heterocyclic carbene, which is unexpected knowing that usually a silylene is a weaker bound ligand compared to a carbene. High-level DFT calculations on a small model system and the experimentally used complexes confirm the experimental findings and indicate that steric interactions play an important role in the substitution reaction.

Original languageEnglish
Pages (from-to)3292-3299
Number of pages8
JournalJournal of Organometallic Chemistry
Volume690
Issue number13
DOIs
StatePublished - 1 Jul 2005

Keywords

  • DFT calculations
  • N-Heterocyclic carbene
  • N-Heterocyclic silylene
  • Palladium
  • Steric repulsion

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