A copper complex bearing a TEMPO moiety as catalyst for the aerobic oxidation of primary alcohols - Archive ouverte HAL
Article Dans Une Revue Dalton Transactions Année : 2008

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

Résumé

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-p and hydrogen bonding interactions. In addition, the solid state structure of 8 exhibits (lone-pair)-p 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.

Domaines

Matériaux

Dates et versions

hal-00688205 , version 1 (17-04-2012)

Identifiants

Citer

Zhengliang Lu, Josésanchez Costa, Olivier Roubeau, Ilpo Mutikainen, Urho Turpeinen, et al.. A copper complex bearing a TEMPO moiety as catalyst for the aerobic oxidation of primary alcohols. Dalton Transactions, 2008, pp. 3567-3573. ⟨10.1039/b802109k⟩. ⟨hal-00688205⟩

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