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Issue 21, 2005
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Selective copper(II)-mediated oxidative coupling of a nucleophilic reagent to the para-methyl group of 2,4,6-trimethylphenol

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Abstract

A copper(II) neocuproine system has been developed for the efficient and very selective 1,6-addition of a nucleophile to the para-methyl group of 2,4,6-trimethylphenol. Crystallographic and spectroscopic data point towards the involvement of a μ-methoxo–μ-phenoxo-bridged copper species which appears to generate a highly reactive quinone methide intermediate that can be attacked by a nucleophilic reagent.

Graphical abstract: Selective copper(ii)-mediated oxidative coupling of a nucleophilic reagent to the para-methyl group of 2,4,6-trimethylphenol

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Publication details

The article was received on 20 May 2005, accepted on 04 Jul 2005 and first published on 26 Sep 2005


Article type: Paper
DOI: 10.1039/B507199B
Citation: Dalton Trans., 2005,0, 3535-3541
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    Selective copper(II)-mediated oxidative coupling of a nucleophilic reagent to the para-methyl group of 2,4,6-trimethylphenol

    C. Boldron, Ş. Özalp-Yaman, P. Gamez, D. M. Tooke, A. L. Spek and J. Reedijk, Dalton Trans., 2005, 0, 3535
    DOI: 10.1039/B507199B

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