1,2-Addition of Diethylzinc to a Bis(Imidazolyl)ketone Ligand

In this study, the selective 1,2-addition of diethylzinc to the ketone functionality of BMdiPhIK [bis(1-methyl-4,5-diphenylimidazolyl)ketone] is shown. The reaction product is isolated in a dimeric form with a planar Zn2(µ-O)2-motif keeping the two monomers together. This compound can serve as a mod...

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Veröffentlicht in:European journal of inorganic chemistry. - 1998. - 2018(2018), 10 vom: 14. März, Seite 1167-1175
1. Verfasser: Folkertsma, Emma (VerfasserIn)
Weitere Verfasser: Benthem, Sanne H, Jastrzebski, Johann T B H, Lutz, Martin, Moret, Marc-Etienne, Klein Gebbink, Robertus J M
Format: Online-Aufsatz
Sprache:English
Veröffentlicht: 2018
Zugriff auf das übergeordnete Werk:European journal of inorganic chemistry
Schlagworte:Journal Article Homogeneous catalysis Radical reactions Reactive intermediates Zinc
Beschreibung
Zusammenfassung:In this study, the selective 1,2-addition of diethylzinc to the ketone functionality of BMdiPhIK [bis(1-methyl-4,5-diphenylimidazolyl)ketone] is shown. The reaction product is isolated in a dimeric form with a planar Zn2(µ-O)2-motif keeping the two monomers together. This compound can serve as a model for reactive intermediates in the catalytic alkylation of ketones with diorganozinc reagents. Hydrolysis of this binuclear zinc compound leads to isolation of the C-alkylated product in 89 % yield. A reaction pathway is proposed in which BMdiPhIK initially coordinates to diethylzinc as a bidentate bis(nitrogen) ligand. This is followed by the homolytic cleavage of the Zn-Et bond and in-cage recombination of the Et-radical and the Zn-coordinated ligand-centered radical, which is mainly localized on the carbonyl moiety of the ligand
Beschreibung:Date Revised 27.03.2024
published: Print-Electronic
Citation Status PubMed-not-MEDLINE
ISSN:1434-1948
DOI:10.1002/ejic.201701363