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Formation of exceptionally weak C–C bonds by metal-templated pinacol coupling

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Abstract

The ability of the bis(imidazolyl)ketone ligand BMdiPhIK (bis(1-methyl-4,5-diphenylimidazolyl)ketone) to function as a redox active ligand has been investigated. The reduction of [M(BMdiPhIK)Cl2] (M = Fe and Zn) complexes resulted in a pinacol-type coupling to form dinuclear complexes featuring very weak and abnormally elongated C–C bonds (1.729(5) and 1.708(3) Å for Fe and Zn, respectively). Oxidation of these complexes using ferrocenium in the presence of Cl ions regenerated the original [M(BMdiPhIK)Cl2] complexes, showing the reversibility of the coupling process. This makes it a potentially interesting approach for the storage of electrons and application of the BMdiPhIK ligand as a redox active ligand.

Graphical abstract: Formation of exceptionally weak C–C bonds by metal-templated pinacol coupling

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Publication details

The article was received on 29 Mar 2017, accepted on 10 Apr 2017 and first published on 10 Apr 2017


Article type: Communication
DOI: 10.1039/C7DT01130J
Citation: Dalton Trans., 2017, Advance Article
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    Formation of exceptionally weak C–C bonds by metal-templated pinacol coupling

    E. Folkertsma, S. H. Benthem, L. Witteman, C. A. M. R. van Slagmaat, M. Lutz, R. J. M. Klein Gebbink and M.-E. Moret, Dalton Trans., 2017, Advance Article , DOI: 10.1039/C7DT01130J

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