Issue 27, 2008
From the journal:

Dalton Transactions

A copper complex bearing a TEMPO moiety as catalyst for the aerobic oxidation of primary alcohols†

Zhengliang Lu,a   José Sánchez Costa,a   Olivier Roubeau,b   Ilpo Mutikainen,c   Urho Turpeinen,c   Simon J. Teat,d   Patrick Gamez*a  and  Jan Reedijk*a  

* Corresponding authors

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

b Université Bordeaux 1, CNRS-CRPP, 115 avenue du dr. A. Schweitzer, Pessac, France

c University of Helsinki, Department of Chemistry, Laboratory of Inorganic Chemistry, Helsinki, Finland

d ALS, Berkeley Lab, 1 Cyclotron Road, MS2-400, Berkeley, CA, USA

Abstract

A new bifunctional, triazine-based ligand has been designed with the aim to generate a copper(II) complex holding a TEMPO (2,2,6,6-tetramethylpiperidinyloxy) moiety. The coordination compound obtained from the ligand 4-(2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)ethoxy)-6-(4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl)-N,N-diphenyl-1,3,5-triazin-2-amine (pypzt-1) and copper(II) bromide (i.e. complex 8) is capable of catalysing the selective, aerobic oxidation of benzyl alcohol to 84% of benzaldehyde in 24 h. This “galactose oxidase activity” of the copper/TEMPO complex is observed as well for the conversion of the non-activated alkyl alcohol octan-1-ol to octanal with a yield of 29% after the same reaction time. The single-crystal X-ray structure of 8 shows that its crystal lattice contains [CuIBr2]− anions which appear to be stabilised by means of both anion–π and hydrogen bonding interactions. In addition, the solid state structure of 8 exhibits (lone-pair)–π interactions between the nitrogen atom of an acetonitrile molecule and a triazine ring. The magnetic properties of 8 have been investigated by EPR and magnetic susceptibility measurements.

Graphical abstract: A copper complex bearing a TEMPO moiety as catalyst for the aerobic oxidation of primary alcohols

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Article information

DOI
https://doi.org/10.1039/B802109K
Article type
Paper
Submitted
06 Feb 2008
Accepted
11 Apr 2008
First published
07 May 2008

Dalton Trans., 2008, 3567-3573

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A copper complex bearing a TEMPO moiety as catalyst for the aerobic oxidation of primary alcohols

Z. Lu, J. S. Costa, O. Roubeau, I. Mutikainen, U. Turpeinen, S. J. Teat, P. Gamez and J. Reedijk, Dalton Trans., 2008, 3567 DOI: 10.1039/B802109K

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