Dalton Transactions (Print Edition) 2014-08-07

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

Hong-Jie Chen, I-Jui Hsu, Mei-Chun Tseng, Shin-Guang Shyu

Index: Dalton Trans. 43(29) , 11410-7, (2014)

Full Text: HTML

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.

Related Compounds

  • 4-Bromotoluene

Related Articles:

Tetragonal Cu2Se nanoflakes: synthesis using selenated propylamine as Se source and activation of Suzuki and Sonogashira cross coupling reactions.

2015-01-14

[Dalton Trans. 44(2) , 725-32, (2014)]

Fluorogenic derivatization of aryl halides based on the formation of biphenyl by Suzuki coupling reaction with phenylboronic acid

2009-01-01

[J. Chromatogr. A. 1216(40) , 6873-6, (2009)]

Synthesis of ketones from alpha-oxocarboxylates and aryl bromides by Cu/Pd-catalyzed decarboxylative cross-coupling.

2008-01-01

[Angew. Chem. Int. Ed. Engl. 47(16) , 3043-5, (2008)]

Successful application of microstructured continuous reactor in the palladium catalysed aromatic amination. Mauger C, et al.

[J. Organomet. Chem. 690(16) , 3627-29, (2005)]

Triaryl phosphine-functionalized N-heterocyclic carbene ligands for Heck reaction. Wang A-E, et al.

[Tetrahedron 61(1) , 259-66, (2005)]

More Articles...