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Palladation of diimidazolium salts at the C4 position: access to remarkably electron-rich palladium(II) centers

  • Heckenroth, Marion Department of Chemistry, University of Fribourg, Switzerland
  • Kluser, Evelyne Department of Chemistry, University of Fribourg, Switzerland
  • Neels, Antonia CSEM Centre Suisse d'Electronique et de Microtechnique, Neuchâtel, Switzerland
  • Albrecht, Martin Department of Chemistry, University of Fribourg, Switzerland
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  • Dalton Transactions. - 2008, p. 6242 - 6249
English Palladation of C2-protected diimidazolium salts with Pd(OAc)₂ afforded complexes comprising C4-bound N-heterocyclic dicarbene ligands. The reactivity of these complexes towards Lewis acids (AgBF₄, AgOAc) and Brønsted acids (H₂SO₄, H₃PO₄, HOAc) revealed that abnormal C4 bonding of the carbenes markedly increases the nucleophilicity of the coordinated palladium center as compared to C2 bonding. Despite its formal +2 charge, the palladium center in these complexes is best described as a Lewis base. The abnormal carbene bonding mode induces new reaction patterns such as the formation of a Pd–Ag adduct. Based on metallation studies including the palladation of a dissymmetric diimidazolium salt, a rationale for the selective activation of the C4–H bond in the diimidazolium precursor salts is proposed.
Faculté des sciences et de médecine
Département de Chimie
  • English
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