Formation of Exceptionally Weak C–C Bonds by Metal-Templated Pinacol Coupling

Emma Folkertsma; Sanne H. Benthem; Léon Witteman; Christian A. M. R. Van Slagmaat; Martin Lutz; Robertus J.m. Klein Gebbink; Marc-etienne Moret

doi:10.1039/C7DT01130J

Formation of Exceptionally Weak C–C Bonds by Metal-Templated Pinacol Coupling

Emma Folkertsma, Sanne H. Benthem, Léon Witteman, Christian A. M. R. Van Slagmaat, Martin Lutz, Robertus J.m. Klein Gebbink, Marc-etienne Moret^*

^*Corresponding author for this work

Sub Organic Chemistry and Catalysis

Research output: Contribution to journal › Article › Academic › peer-review

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

Original language	English
Pages (from-to)	6177-6182
Number of pages	6
Journal	Dalton Transactions
Volume	46
Issue number	19
DOIs	https://doi.org/10.1039/C7DT01130J
Publication status	Published - 10 Apr 2017

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title = "Formation of Exceptionally Weak C–C Bonds by Metal-Templated Pinacol Coupling",

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) {\AA} 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",

author = "Emma Folkertsma and Benthem, {Sanne H.} and L{\'e}on Witteman and {Van Slagmaat}, {Christian A. M. R.} and Martin Lutz and {Klein Gebbink}, {Robertus J.m.} and Marc-etienne Moret",

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language = "English",

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T1 - Formation of Exceptionally Weak C–C Bonds by Metal-Templated Pinacol Coupling

AU - Folkertsma, Emma

AU - Benthem, Sanne H.

AU - Witteman, Léon

AU - Van Slagmaat, Christian A. M. R.

AU - Lutz, Martin

AU - Klein Gebbink, Robertus J.m.

AU - Moret, Marc-etienne

PY - 2017/4/10

Y1 - 2017/4/10

N2 - 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

AB - 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

U2 - 10.1039/C7DT01130J

DO - 10.1039/C7DT01130J

M3 - Article

SN - 1477-9226

VL - 46

SP - 6177

EP - 6182

JO - Dalton Transactions

JF - Dalton Transactions

IS - 19

ER -

Formation of Exceptionally Weak C–C Bonds by Metal-Templated Pinacol Coupling

Abstract

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