Selenium catalysed oxidations with aqueous hydrogen peroxide. Part 3: Oxidation of carbonyl compounds under mono/bi/triphasic conditions

Brink, Gerd‐Jan ten; Vis, Jan‐Martijn; Arends, Isabel W. C. E.; Sheldon, Roger A.

doi:10.1016/s0040-4020(02)00248-x

Cited by 90 publications

(54 citation statements)

References 35 publications

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“…The reaction was also carried out in the presence of traces of sodium acetate (0.5 mol%) to control the pH of the reaction medium and to minimize the hydrolysis suffered by the epoxide [25][26][27], which can be observed in entries 7 and 8 of Table 4. Although the reaction is slightly slower in these conditions, the hydrolysis was totally avoided.…”

Section: Epoxidation Of Cyclohexenementioning

confidence: 99%

“…Moreover diselenides can be easily oxidized in situ by hydrogen peroxide to seleninic acid or peroxyseleninic acid, which are in some cases excellent catalysts in the oxidation of organic compounds [21][22][23][24], as, for instance, epoxidation reaction of alkenes [25], Baeyer-Villiger reaction [26], oxidation of carbonyl compounds [27], dehydrogenation of carbonyl compounds [28][29], oxidation of secondary amines [30][31], oxidation of imines [32], or selenenylations or halogenations [33].…”

Section: Introductionmentioning

confidence: 99%

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Epoxidation of cyclooctene and cyclohexene with hydrogen peroxide catalyzed by bis[3,5-bis(trifluoromethyl)-diphenyl] diselenide: Recyclable catalyst-containing phases through the use of glycerol-derived solvents

García-Marín

Toorn

Mayoral

et al. 2011

Journal of Molecular Catalysis A: Chemical

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A green strategy has been explored for olefin epoxidation which combines renewable solvents (derived from glycerol), aqueous hydrogen peroxide, and catalyst recycling (a seleninic acid derivative). The use of fluorinated glycerol derivatives allows good catalytic activity in the epoxidation of cyclooctene and cyclohexene with aqueous hydrogen peroxide, preventing epoxide hydrolysis to a great extent, which is particularly remarkable in the case of cyclohexene. Furthermore, recycling of the catalytically active phase is possible through distillation of the cyclohexene oxide from the reaction mixture, which can be subsequently recharged with fresh oxidant and substrate.

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Section: Epoxidation Of Cyclohexenementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Epoxidation of cyclooctene and cyclohexene with hydrogen peroxide catalyzed by bis[3,5-bis(trifluoromethyl)-diphenyl] diselenide: Recyclable catalyst-containing phases through the use of glycerol-derived solvents

García-Marín

Toorn

Mayoral

et al. 2011

Journal of Molecular Catalysis A: Chemical

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“…22 The oxidation with the H 2 O 2 -PADS system can be explained according to the mechanism postulated earlier for other diaryl diselenides. 2,23 In this case the compound 24, oxidized with hydrogen peroxide, underwent depolymerization to produce areneseleninic acid 36 which was subsequently converted into peroxyseleninic acid 37 (Scheme 10). …”

Section: Methodsmentioning

confidence: 99%

Diaryl diselenides and benzisoselenazol-3(2H)-ones as oxygen-transfer agents

Młochowski¹,

Brzaszcz²,

Chojnacka³

et al. 2004

Arkivoc

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Diaryl diselenides and related benzisoselenazol-3(2H)-ones are presented as the catalyst for hydogen peroxide and t-butylhydroperoxide oxidation of various types of organic substrates. Most of the reactions studied in our laboratory have a practical value. The aromatic aldehydes and ketones are oxidized to arenecarboxylic acids or converted to the phenols while cycloalkanones gave cycloalkanecarboxylic acids with ring contraction. From the azomethine compounds, depending on their structure, nitriles, parent carbonyl compounds, carboxylic acids or their esters are produced. Primary benzylamines gave nitriles, while the secondary are oxidized to nitrones. Alkylarenes are oxidized to the alkylaryl ketones and alkenes to epoxides. By oxidation of 1,4-dimethoxysubstituted and some polycondensed arenes the quinones are produced. The postulated mechanisms are discussed and the methods for synthesis of the title compounds are described.

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“…The reaction required 1,1,1,3,3,3-hexafluoro-2-propanol, 2,2,2-trifluoroethanol, or dichloromethane as solvents and resulted in the formation of lactones (esters) or carboxylic acid, starting from ketones or aldehydes, respectively [57]. In addition, the same authors found that 3,5-bis(perfluorooctyl)benzeneseleninic acid can efficiently catalyze the oxidation of aldehydes as well as ketones using an aqueous solution of hydrogen peroxide in monophasic, fluorous biphasic, or triphasic reaction media [58]. In 2015 some of the present authors demonstrated that benzeneseleninic acid under "on-water" conditions oxidizes a number of aldehydes into the corresponding carboxylic acids when the medium is water or, alternatively, into the corresponding esters when the medium is an alcohol [59].…”

Section: Water As An Alternative Medium For Organoselenium-catalyzed mentioning

confidence: 98%

Water and Aqueous Mixtures as Convenient Alternative Media for Organoselenium Chemistry

et al. 2016

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Abstract:Even if water is the natural environment for bioorganic reactions, its use in organic chemistry is often severely limited by the high insolubility of the organic derivatives. In this review, we introduce some examples of the use of water to perform organoselenium chemistry. We mainly discuss the advantages of this medium when the recyclability is demonstrated and when the water can control the selectivity of a reaction or enhance the reaction rate.

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Selenium catalysed oxidations with aqueous hydrogen peroxide. Part 3: Oxidation of carbonyl compounds under mono/bi/triphasic conditions

Cited by 90 publications

References 35 publications

Epoxidation of cyclooctene and cyclohexene with hydrogen peroxide catalyzed by bis[3,5-bis(trifluoromethyl)-diphenyl] diselenide: Recyclable catalyst-containing phases through the use of glycerol-derived solvents

Epoxidation of cyclooctene and cyclohexene with hydrogen peroxide catalyzed by bis[3,5-bis(trifluoromethyl)-diphenyl] diselenide: Recyclable catalyst-containing phases through the use of glycerol-derived solvents

Diaryl diselenides and benzisoselenazol-3(2H)-ones as oxygen-transfer agents

Water and Aqueous Mixtures as Convenient Alternative Media for Organoselenium Chemistry

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