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Article Dans Une Revue Dalton Transactions Année : 2009

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

Ibrahim Abdellah
Yves Canac
Carine Duhayon
Remi Chauvin

Résumé

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 carbon–palladium 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.

Dates et versions

hal-03734167 , version 1 (21-07-2022)

Identifiants

Citer

Ibrahim Abdellah, Nathalie Debono, Yves Canac, Carine Duhayon, Remi Chauvin. Atropochiral (C,C)-chelating NHC-ylide ligands: synthesis and resolution of palladium(ii) complexes thereof. Dalton Transactions, 2009, 35, pp.7196-7202. ⟨10.1039/B907019B⟩. ⟨hal-03734167⟩
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