Issue 21, 2005
From the journal:

Dalton Transactions

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

Christophe Boldron,a   Şeniz Özalp-Yaman,§a   Patrick Gamez,a   Duncan M. Tooke,b   Anthony L. Spekb  and  Jan Reedijk*a  

* Corresponding authors

a Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, P.O. Box 9502, RA Leiden, The Netherlands
E-mail: reedijk@chem.leidenuniv.nl
Fax: 31 715274671
Tel: 31 715274459

b Department of Crystal and Structural Chemistry, University Utrecht, Padualaan 8, CH Utrecht, The Netherlands

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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Article information

DOI
https://doi.org/10.1039/B507199B
Article type
Paper
Submitted
20 May 2005
Accepted
04 Jul 2005
First published
26 Sep 2005

Dalton Trans., 2005, 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, 3535 DOI: 10.1039/B507199B

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