Issue 8, 2016

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

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

Article type
Research Article
Submitted
16 May 2016
Accepted
10 Jun 2016
First published
13 Jun 2016

Org. Chem. Front., 2016,3, 975-978

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements