Low-temperature oxidation of isopropylbenzene mediated by the system of NHPI, Fe(acac)3 and 1,10-phenanthroline

Highly efficient oxidation of isopropylbenzene mediated by the system of NHPI/Fe(acac)3/Phen has been carried out at temperature as low as 60 °C. Significant improvement of catalysis by NHPI was associated with an enhanced oxidizing ability of Fe(III) tandem with Phen, which caused the intense gener...

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Main Authors: N.I. Kuznetsova, D.E. Babushkin, V.N. Zudin, O.S. Koscheeva, L.I. Kuznetsova
Format: Article
Language:English
Published: Elsevier 2021-01-01
Series:Catalysis Communications
Subjects:
Online Access:http://www.sciencedirect.com/science/article/pii/S1566736720302946
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author N.I. Kuznetsova
D.E. Babushkin
V.N. Zudin
O.S. Koscheeva
L.I. Kuznetsova
author_facet N.I. Kuznetsova
D.E. Babushkin
V.N. Zudin
O.S. Koscheeva
L.I. Kuznetsova
author_sort N.I. Kuznetsova
collection DOAJ
description Highly efficient oxidation of isopropylbenzene mediated by the system of NHPI/Fe(acac)3/Phen has been carried out at temperature as low as 60 °C. Significant improvement of catalysis by NHPI was associated with an enhanced oxidizing ability of Fe(III) tandem with Phen, which caused the intense generation of PINO. Furthermore, NMR observations revealed formation of a hydrogen-bonded NHPI-Phen adduct soluble in acetonitrile and isopropylbenzene. Based on this phenomenon, the system was applicable for the oxidation of solvent-free isopropylbenzene. The promise of the system of NHPI/Fe(acac)3/Phen for the selective synthesis of isopropylbenzene hydroperoxide was demonstrated by oxidation at a low content of Fe(acac)3.
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spelling doaj.art-2400af00531f4c66bb5618f18931e00f2022-12-21T22:24:57ZengElsevierCatalysis Communications1873-39052021-01-01149106218Low-temperature oxidation of isopropylbenzene mediated by the system of NHPI, Fe(acac)3 and 1,10-phenanthrolineN.I. Kuznetsova0D.E. Babushkin1V.N. Zudin2O.S. Koscheeva3L.I. Kuznetsova4Boreskov Institute of Catalysis SB RAS, 5 Prospekt Lavrentieva, Novosibirsk 630090, RF; Corresponding author.Boreskov Institute of Catalysis SB RAS, 5 Prospekt Lavrentieva, Novosibirsk 630090, RFBoreskov Institute of Catalysis SB RAS, 5 Prospekt Lavrentieva, Novosibirsk 630090, RFNikolaev Institute of Inorganic Chemistry SB RAS, 3 Prospect Lavrentueva, Novosibirsk 630090, RFBoreskov Institute of Catalysis SB RAS, 5 Prospekt Lavrentieva, Novosibirsk 630090, RFHighly efficient oxidation of isopropylbenzene mediated by the system of NHPI/Fe(acac)3/Phen has been carried out at temperature as low as 60 °C. Significant improvement of catalysis by NHPI was associated with an enhanced oxidizing ability of Fe(III) tandem with Phen, which caused the intense generation of PINO. Furthermore, NMR observations revealed formation of a hydrogen-bonded NHPI-Phen adduct soluble in acetonitrile and isopropylbenzene. Based on this phenomenon, the system was applicable for the oxidation of solvent-free isopropylbenzene. The promise of the system of NHPI/Fe(acac)3/Phen for the selective synthesis of isopropylbenzene hydroperoxide was demonstrated by oxidation at a low content of Fe(acac)3.http://www.sciencedirect.com/science/article/pii/S1566736720302946OxidationIsopropylbenzeneN-HydroxyphthalimideIron(III) acetylacetonate1,10-PhenantrolineIsopropylbenzene hydroperoxide
spellingShingle N.I. Kuznetsova
D.E. Babushkin
V.N. Zudin
O.S. Koscheeva
L.I. Kuznetsova
Low-temperature oxidation of isopropylbenzene mediated by the system of NHPI, Fe(acac)3 and 1,10-phenanthroline
Catalysis Communications
Oxidation
Isopropylbenzene
N-Hydroxyphthalimide
Iron(III) acetylacetonate
1,10-Phenantroline
Isopropylbenzene hydroperoxide
title Low-temperature oxidation of isopropylbenzene mediated by the system of NHPI, Fe(acac)3 and 1,10-phenanthroline
title_full Low-temperature oxidation of isopropylbenzene mediated by the system of NHPI, Fe(acac)3 and 1,10-phenanthroline
title_fullStr Low-temperature oxidation of isopropylbenzene mediated by the system of NHPI, Fe(acac)3 and 1,10-phenanthroline
title_full_unstemmed Low-temperature oxidation of isopropylbenzene mediated by the system of NHPI, Fe(acac)3 and 1,10-phenanthroline
title_short Low-temperature oxidation of isopropylbenzene mediated by the system of NHPI, Fe(acac)3 and 1,10-phenanthroline
title_sort low temperature oxidation of isopropylbenzene mediated by the system of nhpi fe acac 3 and 1 10 phenanthroline
topic Oxidation
Isopropylbenzene
N-Hydroxyphthalimide
Iron(III) acetylacetonate
1,10-Phenantroline
Isopropylbenzene hydroperoxide
url http://www.sciencedirect.com/science/article/pii/S1566736720302946
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