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Issue 2, 2014
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The C–H bond activation in 1-ethyl-3-methylimidazolium acetate–copper(II) acetate–water–air (dioxygen) systems

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Abstract

Ionic liquid (1-ethyl-3-methylimidazolium acetate, [C2C1im][AcO])–copper(II) diacetate monohydrate–water–air (O2) systems have been investigated by 13C NMR, EPR, spectrophotometry, HPLC, and synthetic chemistry methods at different temperatures. The C–H bond activation of [C2C1im]+ with the formation of the unusual dication 1,1′-diethyl-3,3′-dimethyl-2,2′-biimidazolium ([(C2C1im)2]2+) at 50 °C and 1-ethyl-3-methyl-1H-imidazol-2(3H)-one (C2C1imO) at 50–85 °C was revealed. Two new complexes with the above compounds, [(C2C1im)2][Cu(AcO)4] and Cu2(AcO)4(C2C1imO)2, were isolated from the systems and characterized by X-ray structural analysis. Catalytic cycles with the participation of copper(II) acetate and dioxygen and the production of [(C2C1im)2]2+ and C2C1imO have been proposed. The catalysis presumably includes the formation of the CuII(O2)CuII active centre with μ–η22-peroxide bridging in analogy with tyrosinase and catechol oxidase activity.

Graphical abstract: The C–H bond activation in 1-ethyl-3-methylimidazolium acetate–copper(ii) acetate–water–air (dioxygen) systems

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Publication details

The article was received on 17 Jul 2013, accepted on 26 Sep 2013 and first published on 27 Sep 2013


Article type: Paper
DOI: 10.1039/C3DT51946E
Citation: Dalton Trans., 2014,43, 799-805
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    The C–H bond activation in 1-ethyl-3-methylimidazolium acetate–copper(II) acetate–water–air (dioxygen) systems

    V. G. Shtyrlin, N. Yu. Serov, D. R. Islamov, A. L. Konkin, M. S. Bukharov, O. I. Gnezdilov, D. B. Krivolapov, O. N. Kataeva, G. A. Nazmutdinova and F. Wendler, Dalton Trans., 2014, 43, 799
    DOI: 10.1039/C3DT51946E

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