Synthesis and characterization of oxygen-functionalized-NHC silver(I) complexes and NHC transmetallation to nickel(II). - IFPEN - IFP Energies nouvelles Access content directly
Journal Articles Dalton Transactions Year : 2014

Synthesis and characterization of oxygen-functionalized-NHC silver(I) complexes and NHC transmetallation to nickel(II).

Abstract

The new oxygen-functionalized-NHC silver(I) complexes bis(l-{2,6-diisopropylphenyl)-3-(2-hydroxyethyl)-1H-imidazol-2(3H)-ylidene)silver(I) chloride ([Ag{lmDiPP(EtOH)}2]CI, 4), bis(1-(2-hydroxyethyl)-3-mesityl-1H-imidazol-2(3H)-ylidene )silver(I) chloride ([Ag {lmMes(EtOH) }2]CI, 5),bis(l-(2-hydroxyethyl)-3-methyl-1H-imidazol-2(3H)-ylidene )silvet{l) chloride ([Ag { lmMe(EtOH) }2]Cl, 6), bis( l-(2,6-diisopropylphenyl)-3 -(2-hydroxyethyl)-1 H-imidazol-2(3H)-ylidene)silver(I) tetrafluoroborate ([Ag {ImDiPP(EtOH) }2]BF 4, 9) and bis( l-{2,6-diisopropylphenyl)-3-(2-methoxyethyl)IH-imidazol-2(3H)-ylidene)silver(I) chloride ([Ag{ImDiPP(EtOMe)}2]CI, 13), have been synthesized and fully characterized by NMR spectroscopy and single crystal X-ray diffraction. For some complexes, an uncommon heteronuclear coupling of 4J{'071109 Ag-1H) was unveiled. Their transmetallation ability was assessed in presence of different nickel(II) sources and the bis-NHC Ni{Il) complex bis( 1-(2,6-diisopropylphenyl )-3 -(2-methoxyethyl)-1 H-imidazol-2(3H)-ylidene )nickel{ll) chloride ([NiC12{ImDiPP(Et0Me)} 2], 15) was obtained from 13 and shown by X-ray diffraction to have a transarrangement of the two NHC ligands. In contrast, it was found with the other Ag{I) NHC complexes that the acidity of the alcohol OH proton was detrimental for the transmetallation process, and reprotonation of the CNHc carbon to give the corresponding imidazolium salt was observed.

Domains

Polymers
Fichier principal
Vignette du fichier
article_synthesis_.pdf (507.27 Ko) Télécharger le fichier
Origin : Files produced by the author(s)
Loading...

Dates and versions

hal-01071718 , version 1 (06-10-2014)

Identifiers

Cite

Sophie Hameury, Pierre de Frémont, Pierre-Alain Breuil, Hélène Olivier-Bourbigou, Pierre Braunstein. Synthesis and characterization of oxygen-functionalized-NHC silver(I) complexes and NHC transmetallation to nickel(II).. Dalton Transactions, 2014, 43 (12), pp.4700-4710. ⟨10.1039/c3dt52773e⟩. ⟨hal-01071718⟩
164 View
354 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More