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.

Alcohol oxidation with H2O2 catalyzed by a cheap and promptly available imine based iron complex / Olivo, Giorgio; Giosia, Simone; Barbieri, Alessia; Lanzalunga, Osvaldo; DI STEFANO, Stefano. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - STAMPA. - 14:45(2016), pp. 10630-10635. [10.1039/C6OB01984F]

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

OLIVO, GIORGIO;GIOSIA, SIMONE;BARBIERI, ALESSIA;LANZALUNGA, Osvaldo;DI STEFANO, Stefano
2016

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.
2016
alcohol oxitation; non-heme iron based catalyst; Imine; green oxidations
01 Pubblicazione su rivista::01a Articolo in rivista
Alcohol oxidation with H2O2 catalyzed by a cheap and promptly available imine based iron complex / Olivo, Giorgio; Giosia, Simone; Barbieri, Alessia; Lanzalunga, Osvaldo; DI STEFANO, Stefano. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - STAMPA. - 14:45(2016), pp. 10630-10635. [10.1039/C6OB01984F]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/895529
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