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Issue 8, 2016

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

Supplementary files

Article information


Submitted
16 May 2016
Accepted
10 Jun 2016
First published
13 Jun 2016

Org. Chem. Front., 2016,3, 975-978
Article type
Research Article

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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