Selective synthesis of sulfoxides and sulfones by tantalum(V) catalyzed oxidation of sulfides with 30% hydrogen peroxide

Kirihara, Masayuki; Yamamoto, Junya; Noguchi, Takuya; Hirai, Yoshiro

doi:10.1016/j.tetlet.2008.12.064

Cited by 99 publications

(42 citation statements)

References 41 publications

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“…12 As such there has been considerable interest in developing systems that utilise hydrogen peroxide as the oxidant as it is economical, environmentally benign and readily available. 13 In this regard, a number of systems based on iron, 14 manganese, 15 vanadium, 16 titanium, 17 ruthenium, 18 molybdenum, 19 tungsten, 20 tantalum, 21 rhenium, 22 zinc, 23 tin, 24 and copper 25 have been developed. In addition to utilising hydrogen peroxide as the oxidant, an efficient catalyst must also be highly selective for either sulfoxide or sulfone, cost effective, straightforward to prepare and easy to manipulate, operate under mild conditions across a wide range of substrates, have good long term stability and be easy to recover and recycle.…”

Section: Introductionmentioning

confidence: 99%

Efficient and selective oxidation of sulfides in batch and continuous flow using styrene-based polymer immobilised ionic liquid phase supported peroxotungstates

et al. 2016

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Styrene-based peroxotungstate-modified polymer immobilized ionic liquid phase catalysts [PO4{WO(O2)2}4]@ImPIILP (Im = imidazolium) are remarkably efficient systems for the selective oxidation of sulfides under mild conditions both in batch and as a segmented or continuous flow process using either ethanol or acetonitrile as solvent or mobile phase, respectively. The performance of these styrene-based systems has been compared against their Ring Opening Metathesis Polymerisation derived counterparts to assess their relative merits. A comparative survey revealed catalyst supported on N-benzyl imidazolium decorated polymer immobilised ionic liquid to be the most efficient and a cartridge packed with a mixture of [PO4{WO(O2)2}4]@ImPIILP and silica operated as a segmented or continuous flow system giving good conversions and high selectivity for sulfoxide. The immobilised catalyst remained highly active for the sulfoxidation of thioanisole in ethanol with a stable conversion-selectivity profile for up to 8 h under continuous flow operation; for comparison conversions with a mixture of [NBu4]3[PO4{WO(O2)2}4] and silica dropped dramatically after only 15 min as a result of rapid leaching while [PO4{WO(O2)2}4]@ImPIILP prepared from commercially available Merrifield resin also gave consistently lower conversions; these benchmark comparisons serve to underpin the potential benefits of preparing the polymer immobilized ionic liquid supports.

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Section: Introductionmentioning

confidence: 99%

Efficient and selective oxidation of sulfides in batch and continuous flow using styrene-based polymer immobilised ionic liquid phase supported peroxotungstates

et al. 2016

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“…As we noted in the introduction, we found that methanol is the good solvent for the synthesis of sulfones from the oxidation of sulfides with 30% hydrogen peroxide catalyzed by Nb(V), 10) Ta(V), 10,11) or NbC. 12) Therefore, the reactions of 2-methyl-2-(2-naphthyl)-1,3-dithiane (2a) with 16 eq of 30% hydrogen peroxide in methanol were examined in the presence of 0.1 eq of niobium or tantalum compounds ( Table 1).…”

Section: Resultsmentioning

confidence: 66%

“…We have been working on the oxidations of organosulfur compounds using hydrogen peroxide as the oxidant, and reported that the reaction of sulfides with 30% hydrogen peroxide in the presence of catalytic amounts of Nb(V), 10) Ta(V), 10,11) or niobium carbide (NbC) 12) in methanol provided the corresponding sulfones in high yields (Chart 2).…”

mentioning

confidence: 99%

Niobium(V) Chloride Catalyzed Oxidation of Dithioacetals with 30% Hydrogen Peroxide: A Concise Preparation of Bissulfonylmethylene Compounds

Kirihara

Goto

Noguchi

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…11 Very recently, Rostami and Akradi 12 reported boric acid as a highly efficient and eco-friendly catalyst for the selective oxidation of sulfide to sulfoxide at room temperature under solvent-free condition using 30% H2O2 as an oxidant. We thought to test the oxidation of our sulfides under the same reaction condition.…”

Section: Scheme 1 N-methylthiomethylation Of Benzimidazolesmentioning

confidence: 99%

N-Methylthiomethylation of benzimidazoles with DMSO and their chemoselective oxidation to sulfoxides with NaBiO3

Mukhopadhyay¹,

Tapaswi²,

Sarkar³

et al. 2011

Arkivoc

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A straightforward one-step method for the N-methylthiomethylation of benzimidazoles has been developed employing DMSO as a solvent and as a reagent. This methodology has been applied for the synthesis of diverse N-methylthiomethyl derivatives of benzimidazoles. The products can be chemoselectively oxidized to the corresponding sulfoxides with NaBiO3 in acetic acid. Both the N-methylthiomethyl derivatives of benzimidazoles and their corresponding sulfoxides are important medicinal scaffolds.

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Selective synthesis of sulfoxides and sulfones by tantalum(V) catalyzed oxidation of sulfides with 30% hydrogen peroxide

Cited by 99 publications

References 41 publications

Efficient and selective oxidation of sulfides in batch and continuous flow using styrene-based polymer immobilised ionic liquid phase supported peroxotungstates

Efficient and selective oxidation of sulfides in batch and continuous flow using styrene-based polymer immobilised ionic liquid phase supported peroxotungstates

Niobium(V) Chloride Catalyzed Oxidation of Dithioacetals with 30% Hydrogen Peroxide: A Concise Preparation of Bissulfonylmethylene Compounds

N-Methylthiomethylation of benzimidazoles with DMSO and their chemoselective oxidation to sulfoxides with NaBiO3

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