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  • Title: Atropochiral (C,C)-chelating NHC-ylide ligands: synthesis and resolution of palladium(II) complexes thereof.
    Author: Abdellah I, Debono N, Canac Y, Duhayon C, Chauvin R.
    Journal: Dalton Trans; 2009 Sep 21; (35):7196-202. PubMed ID: 20449163.
    Abstract:
    Atropochiral NHC-phosphonium ylides based on the naphthyl-benzimidazolyl core are targeted as strongly sigma-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 carbon-palladium bonds, while affording the corresponding enantiomeric beta-zwitterionic NHC-ylide palladate complexes. The absolute configuration of the chirally isolated C,C-chelating ligand was finally confirmed by X-ray crystallography.
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