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Issue 33, 2017
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A bis(pyridyl)-N-alkylamine/Cu(i) catalyst system for aerobic alcohol oxidation

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Herein a bis(pyridyl)-N-alkylamine/CuI/TEMPO/NMI catalyst system is reported for aerobic oxidation of a variety of primary alcohols to the corresponding aldehydes using readily available reagents, at room temperature and ambient air as the oxidant. ESI-MS analysis of the reaction showed the formation of a [(L1)(NMI)CuII-OOH]+ species, which is a key intermediate in the alcohol oxidation reaction. Evaluation of the effect of reaction parameters on the initial rate of the reaction allowed us to obtain the optimum conditions for catalytic activity. The careful choice of reaction solvent allowed for the oxidation of 4-hydroxybenzyl alcohol, a substrate which proved problematic in previous studies. In the case of 2-pyridinemethanol as substrate, experimental evidence shows that catalytic activity is diminished due to competitive inhibition of the catalyst by the alcohol substrate.

Graphical abstract: A bis(pyridyl)-N-alkylamine/Cu(i) catalyst system for aerobic alcohol oxidation

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Article information

07 Jun 2017
28 Jul 2017
First published
28 Jul 2017

Org. Biomol. Chem., 2017,15, 6926-6933
Article type

A bis(pyridyl)-N-alkylamine/Cu(I) catalyst system for aerobic alcohol oxidation

L. Marais, J. Burés, J. H. L. Jordaan, S. Mapolie and A. J. Swarts, Org. Biomol. Chem., 2017, 15, 6926
DOI: 10.1039/C7OB01383C

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