Understanding the Regioselectivity of Aromatic Hydroxylation over Divanadium-Substituted γ-Keggin Polyoxotungstate
I. Yu. Skobelev
1, 2
,
Vasilii Yu Evtushok
1, 2
,
O.A. Kholdeeva
1, 2
,
Nataliya V. Maksimchuk
1, 2
,
Raisa I Maksimovskaya
1
,
Josep M. Ricart
3
,
Josep M. Poblet
3
,
Jorge Carbo
3
Publication type: Journal Article
Publication date: 2017-11-15
scimago Q1
wos Q1
SJR: 3.782
CiteScore: 19.5
Impact factor: 13.1
ISSN: 21555435
General Chemistry
Catalysis
Abstract
The aromatic hydroxylation of pseudocumene (PC) with aqueous hydrogen peroxide catalyzed by the divanadium-substituted γ-Keggin polyoxotungstate TBA4[γ-PW10O38V2(μ-O)(μ-OH)] (TBA-1H, TBA = tetrabutylammonium) has been studied using kinetic modeling and DFT calculations. This reaction features high chemoselectivity and unusual regioselectivity, affording 2,4,5-trimethylphenol (TMP) as the main product. Then the computational study was extended to the analysis of the regioselectivity for other alkoxy- and alkylarene substrates. The protonation/deprotonation of TBA-1H in MeCN/tBuOH (1:1) was investigated by 31P NMR spectroscopy. Forms with different protonation states, [γ-PV2W10O40]5– (1), [γ-HPV2W10O40]4– (1H), and [γ-H2PV2W10O40]3– (1H2), have been identified, and the protonation equilibrium constants were estimated on the basis of the 31P NMR data. DFT calculations were used to investigate the oxygen transfer process from hydroperoxo species, [γ-PW10O38V2(μ-O)(μ-OOH)]4– (2) and [γ-PW10O38V2(μ-OH)(μ-OOH)]3...
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Skobelev I. Y. et al. Understanding the Regioselectivity of Aromatic Hydroxylation over Divanadium-Substituted γ-Keggin Polyoxotungstate // ACS Catalysis. 2017. Vol. 7. No. 12. pp. 8514-8523.
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Skobelev I. Y., Evtushok V. Yu., Kholdeeva O., Maksimchuk N. V., Maksimovskaya R. I., Ricart J. M., Poblet J. M., Carbo J. Understanding the Regioselectivity of Aromatic Hydroxylation over Divanadium-Substituted γ-Keggin Polyoxotungstate // ACS Catalysis. 2017. Vol. 7. No. 12. pp. 8514-8523.
Cite this
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TY - JOUR
DO - 10.1021/acscatal.7b02694
UR - https://doi.org/10.1021/acscatal.7b02694
TI - Understanding the Regioselectivity of Aromatic Hydroxylation over Divanadium-Substituted γ-Keggin Polyoxotungstate
T2 - ACS Catalysis
AU - Skobelev, I. Yu.
AU - Evtushok, Vasilii Yu
AU - Kholdeeva, O.A.
AU - Maksimchuk, Nataliya V.
AU - Maksimovskaya, Raisa I
AU - Ricart, Josep M.
AU - Poblet, Josep M.
AU - Carbo, Jorge
PY - 2017
DA - 2017/11/15
PB - American Chemical Society (ACS)
SP - 8514-8523
IS - 12
VL - 7
SN - 2155-5435
ER -
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@article{2017_Skobelev,
author = {I. Yu. Skobelev and Vasilii Yu Evtushok and O.A. Kholdeeva and Nataliya V. Maksimchuk and Raisa I Maksimovskaya and Josep M. Ricart and Josep M. Poblet and Jorge Carbo},
title = {Understanding the Regioselectivity of Aromatic Hydroxylation over Divanadium-Substituted γ-Keggin Polyoxotungstate},
journal = {ACS Catalysis},
year = {2017},
volume = {7},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acscatal.7b02694},
number = {12},
pages = {8514--8523},
doi = {10.1021/acscatal.7b02694}
}
Cite this
MLA
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Skobelev, I. Yu., et al. “Understanding the Regioselectivity of Aromatic Hydroxylation over Divanadium-Substituted γ-Keggin Polyoxotungstate.” ACS Catalysis, vol. 7, no. 12, Nov. 2017, pp. 8514-8523. https://doi.org/10.1021/acscatal.7b02694.
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