Bibliographic Details
| Title: |
Possible intermediates of Cu(phen)-catalyzed C-O cross-coupling of phenol with an aryl bromide by in situ ESI-MS and EPR studies. |
| Authors: |
Hong-Jie Chen1,2, I-Jui Hsu3, Mei-Chun Tseng1, Shin-Guang Shyu1,2 sgshyu@chem.sinica.edu.tw |
| Source: |
Dalton Transactions: An International Journal of Inorganic Chemistry. 2014, Vol. 43 Issue 29, p11410-11417. 8p. |
| Subject Terms: |
*INTERMEDIATES (Chemistry), *COPPER catalysts, *COUPLING reactions (Chemistry), *PHENOLS, *ARYL bromides, *TOLUENE |
| 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. [ABSTRACT FROM AUTHOR] |
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| Database: |
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