Issue 2, 2003

A study of the oxidation of ethers with the enzyme laccase under mediation by two N–OH–type compounds

Abstract

The oxidation of ethers of various structure by O2 with two laccase/[double bond splayed left]N–OH systems (i.e., HBT, 1-hydroxybenzotriazole, and HPI, N-hydroxyphthalimide) is described. The process affords carbonylic products in reasonable-to-good yields. The oxidation is carried out by the intermediate [double bond splayed left]N–O˙ species of the mediators, through a radical H-atom abstraction (HAT) route that represents an elaboration of the HAT route followed with benzyl alcohols. Alternative mechanisms have been considered and dismissed. A comparison with a similar oxidation of ethers by the laccase/TEMPO system, reported previously, is made. A clear-cut specialisation of the mediator vs. the substrate emerges, i.e. the laccase/HBT system is more competent for the oxidation of ethers, whereas the laccase/TEMPO system was most proficient in the oxidation of benzyl alcohols.

Graphical abstract: A study of the oxidation of ethers with the enzyme laccase under mediation by two N–OH–type compounds

Article information

Article type
Paper
Submitted
07 Nov 2002
Accepted
25 Nov 2002
First published
13 Dec 2002

New J. Chem., 2003,27, 329-332

A study of the oxidation of ethers with the enzyme laccase under mediation by two N–OH–type compounds

F. d'Acunzo, P. Baiocco and C. Galli, New J. Chem., 2003, 27, 329 DOI: 10.1039/B210978F

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