A convenient acid-catalyzed oxidation of sulfides to sulfoxides by t-butyl hydroperoxide

Bonadies, F.; Angelis, Francesco De; Locati, L.; Scettri, Arrigo

doi:10.1016/0040-4039(96)01558-4

Cited by 45 publications

(24 citation statements)

References 4 publications

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“…On the other hand, sulfoxide derivatives are known to have interesting and useful biological and pharmacodynamic properties [24]. The sulfoxides are obtained by oxidation of thioethers by peracids, peroxides and alkyl peroxides using transition metal catalysts [25]. Depending on the catalyst selectivity and the method used, different proportions of sulfoxide and sulfone are produced [26].…”

Section: -Introductionmentioning

confidence: 99%

“…In addition, epoxides, produced by the oxidation of olefins, are extremely useful building blocks in the synthesis of organic compounds as they act as excellent intermediates that can yield a great variety of products [27]. When using vanadyl compounds, the catalytically active oxo-peroxo intermediate is formed in situ by oxidation of V(IV) to V(V) with an excess of tert-butyl hydroperoxide, yielding a tert-butyl hydroperoxovanadium(V) complex.In most of the methods described in the literature, pollutants are generated, because of the use of corrosive acids, toxic or dangerous substances [25]. For this reason it is important to develop clean methods which allow obtaining the sulfoxide derivatives and the epoxides without the generation of these undesired substances.…”

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confidence: 99%

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Vanadyl arsenates as catalysts for selective oxidation of organic sulfides and alkenes

Berrocal

Larrea

Iglesias

et al. 2011

Journal of Molecular Catalysis A: Chemical

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Two vanadyl arsenates templated with ethylendiamonium (EnVAs) and piperazonium (PipVAs) were evaluated as catalysts for the oxidation of thioethers and alkenes, using H 2 O 2 and t-butyl hydroperoxide (TBHP) as oxidants. The intrinsic activity of EnVAs was higher than that of PipVAs for the oxidation of sulfides. Similar results were obtained when using either H 2 O 2 or TBHP as oxidants. However, the sterical effects were enhanced when TBHP was used and higher selectivities towards sulfoxides were achieved with this oxidant. The catalytic activity of the V-based materials in the epoxidation of simple alkenes and allylic alcohols was assessed. Upon reuse, both materials show no significant decrease in their catalytic properties. 1.-INTRODUCTIONOpen-framework metal phosphates are of considerable technological importance as shapeselective catalysts, ion-exchange materials and molecular sieves [1]. Since the discovery of the microporous crystalline aluminophosphates AlPO4-n in 1982[2], a large number of new metal phosphates with open-framework structures have been synthesized [3][4][5][6][7]. These structures contain not only tetrahedrally coordinated atoms but also square pyramidal and octahedral moieties. Among the vast family of open-framework metal phosphates, the transition metal phosphates constitute an important group due to their potential activity as redox catalysts. Out of all the open-framework compounds known, those based on the phosphate oxoanion appear to be the predominant class [8][9][10]. In addition to the use of tetrahedral phosphate groups as building units, other anionic moieties such as borates [11] . In addition, epoxides, produced by the oxidation of olefins, are extremely useful building blocks in the synthesis of organic compounds as they act as excellent intermediates that can yield a great variety of products [27]. When using vanadyl compounds, the catalytically active oxo-peroxo intermediate is formed in situ by oxidation of V(IV) to V(V) with an excess of tert-butyl hydroperoxide, yielding a tert-butyl hydroperoxovanadium(V) complex.In most of the methods described in the literature, pollutants are generated, because of the use of corrosive acids, toxic or dangerous substances [25]. For this reason it is important to develop clean methods which allow obtaining the sulfoxide derivatives and the epoxides without the generation of these undesired substances. In this sense, the use of hydrogen peroxide instead of other oxidants for the oxidation of organic substrates is an interesting alternative because the unique subproduct of the reaction is water. In addition, hydrogen peroxide is highly efficient in its oxygen content and is a cheap reagent. 4The use of open framework phases templated with amines as catalysts in these reactions is especially appealing due to their redox properties, including their acidity [22,23,28,29].During the course of our research, we have synthesized two new catalytic compounds, fluoro- was added dropwise, while the overall suspension was heated at 323...

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Section: -Introductionmentioning

confidence: 99%

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confidence: 99%

Vanadyl arsenates as catalysts for selective oxidation of organic sulfides and alkenes

Berrocal

Larrea

Iglesias

et al. 2011

Journal of Molecular Catalysis A: Chemical

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“…The catalytic conversion has been accomplished using reagents such as binuclear manganese complexes periodic acid, N-hydroxyphthalimide-molecular oxygen, sodium perborate and/or sodium percarbonate and silica sulfuric acid in the presence of KBr, manganese(III) complexes with bidentate O,N-donor oxazoline ligand and UHP oxidizing agent, supported nitric acid on silica gel and polyvinylpyrrolidone (PVP) catalyzed by KBr and/or NaBr [12][13][14][15][16][17]. However, some of these methods have drawbacks such as the use of corrosive acids, hazardous peracids and toxic metallic compounds that generate waste streams.…”

Section: Introductionmentioning

confidence: 99%

Keggin heteropolycompounds as catalysts for liquid-phase oxidation of sulfides to sulfoxides/sulfones by hydrogen peroxide

Romanelli

Villabrille

Cáceres

et al. 2011

Catalysis Communications

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H 4 PMo 11 VO 40 , H 5 PMo 10 V 2 O 40 and H 9 PMo 6 V 6 O 40 acids and an acidic pyridinium salt of H 4 PMo 11 VO 40 were synthesized. They were characterized by FT-IR and the variations of their acid properties were determined by titration with n-butylamine. They proved to be highly active and selective catalysts for the hydrogen peroxide oxidation of methyl phenyl sulfide to the corresponding sulfoxide or sulfone. The conversion and selectivity results may be explained in terms of the co-existence of acidic and oxidative properties in the catalysts. On the other hand, a convenient catalytic homogeneous procedure has been found to oxidize different sulfides to sulfoxides or sulfones, with 35% aqueous H 2 O 2 , using (PyH)H 3 PMo 11 VO 40 as catalyst. The oxidation reaction is carried out at room temperature for sulfoxides or 40°C for sulfones and requires a short time. The sulfoxides or sulfones were obtained with excellent yields by controlling the amount of H 2 O 2 .

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“…During the last years, various procedures for H 2 O 2 oxidation of sulfides including the use of various heterogeneous catalyst systems have been reported [4][5][6]. The application of this oxidant has been developed due to its effective oxygen content, eco-friendly nature, low cost, and also safety in storage and operation [7,8]. Recently various heterogenous catalystoxidizing agent systems including gold(III)-hydrogen peroxide [9], silica-immobilized vanadyl alkyl phosphonatesodium bromate [10], silica sulfuric acid-hydrogen peroxide [11], and titanium based catalyst-oxidizing agents have been reported for oxidation of sulfides.…”

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confidence: 99%

Selective and mild oxidation of sulfides to sulfoxides by H2O2 using DBUH-Br3 as catalyst

Bakavoli

Kakhky

Shiri

et al. 2010

Chinese Chemical Letters

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A convenient acid-catalyzed oxidation of sulfides to sulfoxides by t-butyl hydroperoxide

Cited by 45 publications

References 4 publications

Vanadyl arsenates as catalysts for selective oxidation of organic sulfides and alkenes

Vanadyl arsenates as catalysts for selective oxidation of organic sulfides and alkenes

Keggin heteropolycompounds as catalysts for liquid-phase oxidation of sulfides to sulfoxides/sulfones by hydrogen peroxide

Selective and mild oxidation of sulfides to sulfoxides by H2O2 using DBUH-Br3 as catalyst

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