Synthesis of Coenzyme Q0 through Divanadium-Catalyzed Oxidation of 3,4,5-Trimethoxytoluene with Hydrogen Peroxide Full article
| Journal |
Dalton Transactions
ISSN: 1477-9226 , E-ISSN: 1477-9234 |
||||
|---|---|---|---|---|---|
| Output data | Year: 2017, Volume: 46, Number: 16, Pages: 5202-5209 Pages count : 8 DOI: 10.1039/c7dt00552k | ||||
| Tags | Bioactivity; Catalysts; Coenzymes; Hydrogen peroxide; Oxidation; Peroxides; Reaction intermediates | ||||
| Authors |
|
||||
| Affiliations |
|
Funding (2)
| 1 | Russian Foundation for Basic Research | 13-03-12042 |
| 2 | Federal Agency for Scientific Organizations | 0303-2016-0005 |
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.
Cite:
Zalomaeva O.V.
, Evtushok V.Y.
, Maksimov G.M.
, Maksimovskaya R.I.
, Kholdeeva O.A.
Synthesis of Coenzyme Q0 through Divanadium-Catalyzed Oxidation of 3,4,5-Trimethoxytoluene with Hydrogen Peroxide
Dalton Transactions. 2017.
V.46. N16. P.5202-5209. DOI: 10.1039/c7dt00552k
WOS
Scopus
РИНЦ
РИНЦ
ANCAN
PMID
OpenAlex
Synthesis of Coenzyme Q0 through Divanadium-Catalyzed Oxidation of 3,4,5-Trimethoxytoluene with Hydrogen Peroxide
Dalton Transactions. 2017.
V.46. N16. P.5202-5209. DOI: 10.1039/c7dt00552k
WOS
Scopus
РИНЦ
РИНЦ
ANCAN
PMID
OpenAlex
Files:
Full text from publisher
Dates:
| Submitted: | Feb 14, 2017 |
| Accepted: | Mar 17, 2017 |
| Published online: | Mar 20, 2017 |
| Published print: | Apr 28, 2017 |
Identifiers:
| Web of science: | WOS:000399686700013 |
| Scopus: | 2-s2.0-85018466312 |
| Elibrary: | 29501272 | 41772163 |
| Chemical Abstracts: | 2017:448035 |
| Chemical Abstracts (print): | 166:436942 |
| PMID: | 28362448 |
| OpenAlex: | W2598154784 |