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Issue 29, 2014
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Possible intermediates of Cu(phen)-catalyzed C–O cross-coupling of phenol with an aryl bromide by in situ ESI-MS and EPR studies

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Abstract

The C–O coupling reaction between 2,4-dimethylphenol and 4-bromotoluene catalyzed by the CuI/K2CO3/phen system can be inhibited by the radical scavenger cumene. Complexes [Cu(I)(phen)(1-(2,4-dimethylphenoxy)-4-methylbenzene)]+ (denoted as A), {H[Cu(I)(phen)(2,4-dimethylphenoxy)]}+ and [Cu(I)(2,4-dimethylphenoxy)2] (denoted as B) were observed by in situ electrospray ionization mass spectrometry (ESI-MS) analysis of the copper(I)-catalyzed C–O coupling reaction under the catalytic reaction conditions indicating that they could be intermediates in the reaction. The in situ EPR study of the reaction solution detected the Cu(II) species with a fitted g value of 2.188. A catalytic cycle with a single electron transfer (SET) step was proposed based on these observations.

Graphical abstract: Possible intermediates of Cu(phen)-catalyzed C–O cross-coupling of phenol with an aryl bromide by in situ ESI-MS and EPR studies

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Publication details

The article was received on 25 Feb 2014, accepted on 28 May 2014 and first published on 17 Jun 2014


Article type: Paper
DOI: 10.1039/C4DT00582A
Citation: Dalton Trans., 2014,43, 11410-11417
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    Possible intermediates of Cu(phen)-catalyzed C–O cross-coupling of phenol with an aryl bromide by in situ ESI-MS and EPR studies

    H. Chen, I. Hsu, M. Tseng and S. Shyu, Dalton Trans., 2014, 43, 11410
    DOI: 10.1039/C4DT00582A

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