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Effect of different carboxylic acids on the aromatic hydroxylation with H2O2 in the presence of an iron aminopyridine complex. / Tkachenko, Nikolay V.; Lyakin, Oleg Y.; Zima, Alexandra M. et al.

In: Journal of Organometallic Chemistry, Vol. 871, 15.09.2018, p. 130-134.

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Tkachenko NV, Lyakin OY, Zima AM, Talsi EP, Bryliakov KP. Effect of different carboxylic acids on the aromatic hydroxylation with H2O2 in the presence of an iron aminopyridine complex. Journal of Organometallic Chemistry. 2018 Sept 15;871:130-134. doi: 10.1016/j.jorganchem.2018.07.016

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Tkachenko, Nikolay V. ; Lyakin, Oleg Y. ; Zima, Alexandra M. et al. / Effect of different carboxylic acids on the aromatic hydroxylation with H2O2 in the presence of an iron aminopyridine complex. In: Journal of Organometallic Chemistry. 2018 ; Vol. 871. pp. 130-134.

BibTeX

@article{f02def1330854fe5b3425aff0ee4ef4b,
title = "Effect of different carboxylic acids on the aromatic hydroxylation with H2O2 in the presence of an iron aminopyridine complex",
abstract = "In this contribution, the effect of the structure of the catalytic additive – carboxylic acid – on the catalytic performance of the iron based catalyst [(PDP)Fe(OTf)2], 2 (PDP = N,N′-bis(2-pyridylmethyl)-(S,S)-2,2′-bipyrrolidine) in the selective aromatic oxidation of alkylbenzenes with H2O2 is presented. Eight (linear and branched) carboxylic acids have been tested; in the presence of 2-ethylhexanoic acid, the system [(PDP)Fe(OTf)2]/RCOOH/H2O2 has demonstrated the highest substrate conversion and the highest selectivity for oxygen incorporation into the aromatic ring (up to > 99%) at the same time. Low-temperature EPR spectroscopic study of the system [(PDP)Fe(OTf)2]/2-ethylhexanoic acid/H2O2 witness the presence of the low-spin perferryl intermediate 2aEHA with small g-factor anisotropy (g1 = 2.069, g2 = 2.007, g3 = 1.963), which directly reacts with benzene at −80 °C with the rate constant k2 = 0.6 M−1s−1, and with toluene with k2 > 1 M−1s−1, thus giving evidence for its key role in the selective oxygenation of aromatic substrates.",
keywords = "Aromatic oxidation, Electrophilic substitution, Hydrogen peroxide, Intermediates, Iron, Oxidation, OXIDATION, BENZENE, EPR, REACTIVITY, EPOXIDATION, HYDROGEN-PEROXIDE, SELECTIVITY, CATALYSTS, FE",
author = "Tkachenko, {Nikolay V.} and Lyakin, {Oleg Y.} and Zima, {Alexandra M.} and Talsi, {Evgenii P.} and Bryliakov, {Konstantin P.}",
note = "Publisher Copyright: {\textcopyright} 2018 Elsevier B.V.",
year = "2018",
month = sep,
day = "15",
doi = "10.1016/j.jorganchem.2018.07.016",
language = "English",
volume = "871",
pages = "130--134",
journal = "Journal of Organometallic Chemistry",
issn = "0022-328X",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Effect of different carboxylic acids on the aromatic hydroxylation with H2O2 in the presence of an iron aminopyridine complex

AU - Tkachenko, Nikolay V.

AU - Lyakin, Oleg Y.

AU - Zima, Alexandra M.

AU - Talsi, Evgenii P.

AU - Bryliakov, Konstantin P.

N1 - Publisher Copyright: © 2018 Elsevier B.V.

PY - 2018/9/15

Y1 - 2018/9/15

N2 - In this contribution, the effect of the structure of the catalytic additive – carboxylic acid – on the catalytic performance of the iron based catalyst [(PDP)Fe(OTf)2], 2 (PDP = N,N′-bis(2-pyridylmethyl)-(S,S)-2,2′-bipyrrolidine) in the selective aromatic oxidation of alkylbenzenes with H2O2 is presented. Eight (linear and branched) carboxylic acids have been tested; in the presence of 2-ethylhexanoic acid, the system [(PDP)Fe(OTf)2]/RCOOH/H2O2 has demonstrated the highest substrate conversion and the highest selectivity for oxygen incorporation into the aromatic ring (up to > 99%) at the same time. Low-temperature EPR spectroscopic study of the system [(PDP)Fe(OTf)2]/2-ethylhexanoic acid/H2O2 witness the presence of the low-spin perferryl intermediate 2aEHA with small g-factor anisotropy (g1 = 2.069, g2 = 2.007, g3 = 1.963), which directly reacts with benzene at −80 °C with the rate constant k2 = 0.6 M−1s−1, and with toluene with k2 > 1 M−1s−1, thus giving evidence for its key role in the selective oxygenation of aromatic substrates.

AB - In this contribution, the effect of the structure of the catalytic additive – carboxylic acid – on the catalytic performance of the iron based catalyst [(PDP)Fe(OTf)2], 2 (PDP = N,N′-bis(2-pyridylmethyl)-(S,S)-2,2′-bipyrrolidine) in the selective aromatic oxidation of alkylbenzenes with H2O2 is presented. Eight (linear and branched) carboxylic acids have been tested; in the presence of 2-ethylhexanoic acid, the system [(PDP)Fe(OTf)2]/RCOOH/H2O2 has demonstrated the highest substrate conversion and the highest selectivity for oxygen incorporation into the aromatic ring (up to > 99%) at the same time. Low-temperature EPR spectroscopic study of the system [(PDP)Fe(OTf)2]/2-ethylhexanoic acid/H2O2 witness the presence of the low-spin perferryl intermediate 2aEHA with small g-factor anisotropy (g1 = 2.069, g2 = 2.007, g3 = 1.963), which directly reacts with benzene at −80 °C with the rate constant k2 = 0.6 M−1s−1, and with toluene with k2 > 1 M−1s−1, thus giving evidence for its key role in the selective oxygenation of aromatic substrates.

KW - Aromatic oxidation

KW - Electrophilic substitution

KW - Hydrogen peroxide

KW - Intermediates

KW - Iron

KW - Oxidation

KW - OXIDATION

KW - BENZENE

KW - EPR

KW - REACTIVITY

KW - EPOXIDATION

KW - HYDROGEN-PEROXIDE

KW - SELECTIVITY

KW - CATALYSTS

KW - FE

UR - http://www.scopus.com/inward/record.url?scp=85049985652&partnerID=8YFLogxK

U2 - 10.1016/j.jorganchem.2018.07.016

DO - 10.1016/j.jorganchem.2018.07.016

M3 - Article

AN - SCOPUS:85049985652

VL - 871

SP - 130

EP - 134

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

ER -

ID: 14869865