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Issue 45, 2016
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Alcohol oxidation with H2O2 catalyzed by a cheap and promptly available imine based iron complex

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Abstract

We previously reported that the iminopyridine iron(II) complex 1, easily and quantitatively obtainable in situ, can activate H2O2 to form a powerful oxidant, capable of aliphatic C–H bond hydroxylation. In the present study we expand the application of this catalyst to the oxidation of a series of alcohols to the corresponding carbonyl compounds. The oxidation of aliphatic alcohols proceeds smoothly, while that of benzylic alcohols is shown to be challenging. Some collected pieces of evidence suggest a preference of the oxidizing species for the aromatic ring instead for the alcoholic moiety. The decrease of the electron density in the aromatic ring shifts the oxidation from the aromatic towards the alcoholic moiety. Quite surprisingly, preferential oxidation of cyclohexanol versus benzylic alcohol was achieved, showing unprecedented selectivity.

Graphical abstract: Alcohol oxidation with H2O2 catalyzed by a cheap and promptly available imine based iron complex

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Publication details

The article was received on 08 Sep 2016, accepted on 19 Oct 2016 and first published on 19 Oct 2016


Article type: Paper
DOI: 10.1039/C6OB01984F
Citation: Org. Biomol. Chem., 2016,14, 10630-10635
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    Alcohol oxidation with H2O2 catalyzed by a cheap and promptly available imine based iron complex

    G. Olivo, S. Giosia, A. Barbieri, O. Lanzalunga and S. Di Stefano, Org. Biomol. Chem., 2016, 14, 10630
    DOI: 10.1039/C6OB01984F

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