Alcohol oxidation with H 2 O 2 catalyzed by a cheap and promptly available imine based iron complex

We previously reported that the iminopyridine iron(ii) complex 1, easily and quantitatively obtainable in situ, can activate H O 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 al...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2016-12, Vol.14 (45), p.10630-10635
Main Authors: Olivo, Giorgio, Giosia, Simone, Barbieri, Alessia, Lanzalunga, Osvaldo, Di Stefano, Stefano
Format: Article
Language:English
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Summary:We previously reported that the iminopyridine iron(ii) complex 1, easily and quantitatively obtainable in situ, can activate H O 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.
ISSN:1477-0520
1477-0539
DOI:10.1039/C6OB01984F