Article Dans Une Revue Inorganic Chemistry Année : 2020

NHC Core Phosphonium Ylide-based Palladium(II) Pincer Complexes: The Second Ylide Extremity Makes the Difference

Résumé

The coordinating properties of N-heterocyclic carbene (NHC) (A), phenolate (B), and phosphonium ylide (C) moieties were investigated systematically through the preparation of a family of NHC, phosphonium ylide-based pincer ligands, where the third donor extremity can be either an NHC, a phenolate, or a phosphonium ylide. The overall donor character of such ligands [NHC(AaBbCc)] (a + b + c = 2) was analyzed by comparison of the molecular orbitals (energy and shape), oxidation potentials (Epox), and IR νCO and νCN stretching frequencies of their isostructural pincer Pd(II) complexes [NHC(AaBbCc)PdL][OTf] (L = NCCH3, CO, or CNtBu). The three categories of pincer complexes based on phosphonium ylides were easily obtained by acidic treatment of their highly stable ortho-metalated Pd(II) precursors prepared in a single step from readily available N-phosphonio-substituted imidazolium salts. Analysis of IR data indicated that NHC and phenolate ligands have a similar donor character but which remains lower than that of the phosphonium ylide. The impact on catalytic performance of the incorporation of a second strongly donating phosphonium ylide into the ligand architecture was illustrated in the Pd-catalyzed allylation of aldehydes.

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hal-02612432 , version 1 (06-11-2020)

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Rachid Taakili, Cécile Barthes, Amel Goëffon, Christine Lepetit, Carine Guyard-Duhayon, et al.. NHC Core Phosphonium Ylide-based Palladium(II) Pincer Complexes: The Second Ylide Extremity Makes the Difference. Inorganic Chemistry, 2020, 59 (10), pp.7082-7096. ⟨10.1021/acs.inorgchem.0c00561⟩. ⟨hal-02612432⟩
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