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Synthesis of coenzyme Q0 through divanadium-catalyzed oxidation of 3,4,5-trimethoxytoluene with hydrogen peroxide. / Zalomaeva, Olga V.; Evtushok, Vasilii Yu; Maksimov, Gennadii M. et al.

In: Dalton Transactions, Vol. 46, No. 16, 28.04.2017, p. 5202-5209.

Research output: Contribution to journal › Article › peer-review

Harvard

Zalomaeva, OV, Evtushok, VY, Maksimov, GM, Maksimovskaya, RI & Kholdeeva, OA 2017, 'Synthesis of coenzyme Q0 through divanadium-catalyzed oxidation of 3,4,5-trimethoxytoluene with hydrogen peroxide', Dalton Transactions, vol. 46, no. 16, pp. 5202-5209. https://doi.org/10.1039/c7dt00552k

APA

Zalomaeva, O. V., Evtushok, V. Y., Maksimov, G. M., Maksimovskaya, R. I., & Kholdeeva, O. A. (2017). Synthesis of coenzyme Q0 through divanadium-catalyzed oxidation of 3,4,5-trimethoxytoluene with hydrogen peroxide. Dalton Transactions, 46(16), 5202-5209. https://doi.org/10.1039/c7dt00552k

Vancouver

Zalomaeva OV, Evtushok VY, Maksimov GM, Maksimovskaya RI, Kholdeeva OA. Synthesis of coenzyme Q0 through divanadium-catalyzed oxidation of 3,4,5-trimethoxytoluene with hydrogen peroxide. Dalton Transactions. 2017 Apr 28;46(16):5202-5209. doi: 10.1039/c7dt00552k

Author

Zalomaeva, Olga V. ; Evtushok, Vasilii Yu ; Maksimov, Gennadii M. et al. / Synthesis of coenzyme Q0 through divanadium-catalyzed oxidation of 3,4,5-trimethoxytoluene with hydrogen peroxide. In: Dalton Transactions. 2017 ; Vol. 46, No. 16. pp. 5202-5209.

BibTeX

@article{5836ed009fe042488523827c70bc11aa,
title = "Synthesis of coenzyme Q0 through divanadium-catalyzed oxidation of 3,4,5-trimethoxytoluene with hydrogen peroxide",
abstract = "The selective oxidation of methoxy/methyl-substituted arenes to the corresponding benzoquinones has been first realized using aqueous hydrogen peroxide as a green oxidant, acid tetrabutylammonium salts of the γ-Keggin divanadium-substituted phosphotungstate [γ-PW10O38V2(μ-O)2]5- (I) as a catalyst, and MeCN as a solvent. The presence of the dioxovanadium core in the catalyst is crucial for the catalytic performance. The reaction requires an acid co-catalyst or, alternatively, a highly protonated form of I can be prepared and employed. The industrially relevant oxidation of 3,4,5-trimethoxytoluene gives 2,3-dimethoxy-5-methyl-1,4-benzoquinone (ubiquinone 0 or coenzyme Q0, the key intermediate for coenzyme Q10 and other essential biologically active compounds) with 73% selectivity at 76% arene conversion. The catalyst retains its structure under turnover conditions and can be easily recycled and reused without significant loss of activity and selectivity.",
keywords = "SELECTIVE OXIDATION, P-BENZOQUINONES, PHENOLS, TRIMETHOXYBENZENES, METHOXYBENZENES, METHOXYARENES, HYDROXYLATION, QUINONE",
author = "Zalomaeva, {Olga V.} and Evtushok, {Vasilii Yu} and Maksimov, {Gennadii M.} and Maksimovskaya, {Raisa I.} and Kholdeeva, {Oxana A.}",
year = "2017",
month = apr,
day = "28",
doi = "10.1039/c7dt00552k",
language = "English",
volume = "46",
pages = "5202--5209",
journal = "Dalton Transactions",
issn = "1477-9226",
publisher = "Royal Society of Chemistry",
number = "16",

}

RIS

TY - JOUR

T1 - Synthesis of coenzyme Q0 through divanadium-catalyzed oxidation of 3,4,5-trimethoxytoluene with hydrogen peroxide

AU - Zalomaeva, Olga V.

AU - Evtushok, Vasilii Yu

AU - Maksimov, Gennadii M.

AU - Maksimovskaya, Raisa I.

AU - Kholdeeva, Oxana A.

PY - 2017/4/28

Y1 - 2017/4/28

N2 - The selective oxidation of methoxy/methyl-substituted arenes to the corresponding benzoquinones has been first realized using aqueous hydrogen peroxide as a green oxidant, acid tetrabutylammonium salts of the γ-Keggin divanadium-substituted phosphotungstate [γ-PW10O38V2(μ-O)2]5- (I) as a catalyst, and MeCN as a solvent. The presence of the dioxovanadium core in the catalyst is crucial for the catalytic performance. The reaction requires an acid co-catalyst or, alternatively, a highly protonated form of I can be prepared and employed. The industrially relevant oxidation of 3,4,5-trimethoxytoluene gives 2,3-dimethoxy-5-methyl-1,4-benzoquinone (ubiquinone 0 or coenzyme Q0, the key intermediate for coenzyme Q10 and other essential biologically active compounds) with 73% selectivity at 76% arene conversion. The catalyst retains its structure under turnover conditions and can be easily recycled and reused without significant loss of activity and selectivity.

AB - The selective oxidation of methoxy/methyl-substituted arenes to the corresponding benzoquinones has been first realized using aqueous hydrogen peroxide as a green oxidant, acid tetrabutylammonium salts of the γ-Keggin divanadium-substituted phosphotungstate [γ-PW10O38V2(μ-O)2]5- (I) as a catalyst, and MeCN as a solvent. The presence of the dioxovanadium core in the catalyst is crucial for the catalytic performance. The reaction requires an acid co-catalyst or, alternatively, a highly protonated form of I can be prepared and employed. The industrially relevant oxidation of 3,4,5-trimethoxytoluene gives 2,3-dimethoxy-5-methyl-1,4-benzoquinone (ubiquinone 0 or coenzyme Q0, the key intermediate for coenzyme Q10 and other essential biologically active compounds) with 73% selectivity at 76% arene conversion. The catalyst retains its structure under turnover conditions and can be easily recycled and reused without significant loss of activity and selectivity.

KW - SELECTIVE OXIDATION

KW - P-BENZOQUINONES

KW - PHENOLS

KW - TRIMETHOXYBENZENES

KW - METHOXYBENZENES

KW - METHOXYARENES

KW - HYDROXYLATION

KW - QUINONE

UR - http://www.scopus.com/inward/record.url?scp=85018466312&partnerID=8YFLogxK

U2 - 10.1039/c7dt00552k

DO - 10.1039/c7dt00552k

M3 - Article

AN - SCOPUS:85018466312

VL - 46

SP - 5202

EP - 5209

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1477-9226

IS - 16

ER -

ID: 10262713