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

ABSTRACT: In this study, the selective 1,2-addition of diethylzinc to the ketone functionality of BM^diPhIK [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 BM^diPhIK 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 liga

SUBMITTER: Folkertsma E 

PROVIDER: S-EPMC5993287 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature