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Issue 44, 2008
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Palladation of diimidazolium salts at the C4 position: access to remarkably electron-rich palladium(ii) centers

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Abstract

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.

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

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Supplementary files

Article information


Submitted
21 Jul 2008
Accepted
21 Aug 2008
First published
01 Oct 2008

Dalton Trans., 2008, 6242-6249
Article type
Paper

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

M. Heckenroth, E. Kluser, A. Neels and M. Albrecht, Dalton Trans., 2008, 6242
DOI: 10.1039/B812405A

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