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Issue 35, 2009
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Atropochiral (C,C)-chelating NHC-ylide ligands: synthesis and resolution of palladium(II) complexes thereof

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Abstract

Atropochiral NHC-phosphonium ylides based on the naphthyl-benzimidazolyl core are targeted as strongly σ-donor C,C-chelating ligands of transition metals. The ligand core is shown to act in either a monodentate (through the carbene center) or bidentate (through the carbene and the ylide centers) fashion in seven palladium(II) complexes obtained by two sequential strategies. In particular, the enantiomerically pure ortho-palladated (S)-dimethyl(1-phenylethyl)amine co-ligand is used as the chiral resolving agent for the separation of diastereoisomeric NHC-ylide complexes by fractional crystallization. Hydrochloric treatment of either diastereoisomer was found to keep intact the two carbonpalladium bonds, while affording the corresponding enantiomeric β-zwitterionic NHC-ylide palladate complexes. The absolute configuration of the chirally isolated C,C-chelating ligand was finally confirmed by X-ray crystallography.

Graphical abstract: Atropochiral (C,C)-chelating NHC-ylide ligands: synthesis and resolution of palladium(ii) complexes thereof

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Publication details

The article was received on 07 Apr 2009, accepted on 02 Jul 2009 and first published on 23 Jul 2009


Article type: Paper
DOI: 10.1039/B907019B
Citation: Dalton Trans., 2009,0, 7196-7202
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    Atropochiral (C,C)-chelating NHC-ylide ligands: synthesis and resolution of palladium(II) complexes thereof

    I. Abdellah, N. Debono, Y. Canac, C. Duhayon and R. Chauvin, Dalton Trans., 2009, 0, 7196
    DOI: 10.1039/B907019B

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