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Issue 8, 2016
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Aromatic C–H bond cleavage by using a Cu(I) ate-complex

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Abstract

In situ X-ray absorption spectroscopy (XAS), infrared (IR) and nuclear magnetic resonance (NMR) techniques were used to identify the structures and reactivity of copper-containing active intermediates in the sp2 C–H bond cleavage reaction of electron-deficient aromatics. An ate-complex [Cu(OtBu)2]Na was found to be able to cleave the C–H bond of benzothiazole (ArH) producing [ArCuI(OtBu)]Na with a rate constant of 3.2 × 10−2 mol−1 L s−1 at −50 °C and with an activation enthalpy of 0.73 kcal mol−1 at room temperature.

Graphical abstract: Aromatic C–H bond cleavage by using a Cu(i) ate-complex

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Publication details

The article was received on 16 May 2016, accepted on 10 Jun 2016 and first published on 13 Jun 2016


Article type: Research Article
DOI: 10.1039/C6QO00201C
Citation: Org. Chem. Front., 2016,3, 975-978
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    Aromatic C–H bond cleavage by using a Cu(I) ate-complex

    G. Zhang, H. Yi, J. Xin, Y. Deng, R. Bai, Z. Huang, J. T. Miller, A. J. Kropf, E. E. Bunel, X. Qi, Y. Lan and A. Lei, Org. Chem. Front., 2016, 3, 975
    DOI: 10.1039/C6QO00201C

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