Catalyst-free approach for solvent-dependent selective oxidation of organic sulfides with oxone

Yu, Bing; Liu, Anhua; He, Liang‐Nian; Li, Bin; Diao, Zhen‐Feng; Li, Yunong

doi:10.1039/c2gc00027j

Cited by 165 publications

(78 citation statements)

References 70 publications

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“…The high selectivity and conversion obtained in ethanol coupled with its green and sustainable credentials prompted us to use this solvent for the remaining optimisation studies. Systematic variation of the H2O2: substrate mole ratio revealed that the best compromise between conversion and sulfoxide selectivity was obtained for a peroxide to substrate ratio of 2.5; below this ratio conversions were markedly lower (entry 7) while higher ratios gave complete consumption of sulphide but at the expense of selectivity which was markedly lower (entries [8][9][10]. As sulfones are a useful class of compound the conversion-selectivity profile was also monitored as a function of temperature, with a peroxide to substrate ratio of 2.5, in order to identify conditions for the selective formation of methyl phenyl sulfone.…”

Section: Catalysts Synthesis and Batch Catalysismentioning

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: Catalysts Synthesis and Batch Catalysismentioning

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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“…1 In this extremely useful transformation, several oxidants can be employed such as hydrogen peroxide, 2 molecular oxygen, 3 tert-butyl hydroperoxide, 4 cumene hydroperoxide, 5 iodobenzene diacetate, 6 sodium hypochlorite 7 and oxone. 8 Among these oxidants, aqueous hydrogen peroxide is an attractive choice, since it is readily available, inexpensive, easy to operate, safely stored, and environmentally benign with harmless water as the only by-product to be generated in the reaction. 9 But in the absence of catalyst, the oxidation of sulfides to sulfoxides employing aqueous hydrogen peroxide is very slow, especially at room temperature.…”

mentioning

confidence: 99%

Metal-free chemoselective oxidation of sulfides to sulfoxides catalyzed by immobilized taurine and homotaurine in aqueous phase at room temperature

Shen

Zhou

et al. 2015

Tetrahedron Letters

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“…Oxidation of thiazolidin-4-ones to sulfones has been accomplished with H 2 O 2 /Ac 2 O/AcOH (Troutman & Long, 1948), and KMnO 4 (Surrey, 1948). Oxone ® , a mixture of potassium sulfates (2 KHSO 5 /1 K 2 SO 4 /1 KHSO 4 ), is a very desirable material to use because it is a "green" reagent which is inexpensive, safe, and easy to use (Yu, et al, 2012;Hussain, Green & Ahmed, 2013). It has been used as a chemoselective reagent for the oxidation of sulfides to either sulfoxides (Trost & Curran, 1981;Yu, et al, 2012;Webb, 1994;Madesclaire, 1986) or sulfones (Trost & Curran, 1981;Yu, et al, 2012;Webb, 1994;Cannon, et al, 2013;Tierney, et al, 1996).…”

Section: Introductionmentioning

confidence: 99%

“…Oxone ® , a mixture of potassium sulfates (2 KHSO 5 /1 K 2 SO 4 /1 KHSO 4 ), is a very desirable material to use because it is a "green" reagent which is inexpensive, safe, and easy to use (Yu, et al, 2012;Hussain, Green & Ahmed, 2013). It has been used as a chemoselective reagent for the oxidation of sulfides to either sulfoxides (Trost & Curran, 1981;Yu, et al, 2012;Webb, 1994;Madesclaire, 1986) or sulfones (Trost & Curran, 1981;Yu, et al, 2012;Webb, 1994;Cannon, et al, 2013;Tierney, et al, 1996). Selectivity toward the sulfoxide or sulfone has been shown to depend on the amount of Oxone ® used, the temperature, and the solvent (Trost & Curran, 1981;Yu, et al, 2012;Webb, 1994).…”

Section: Introductionmentioning

confidence: 99%

Selective Synthesis of Ortho-substituted 3-Cyclohexyl-2-phenyl-1,3-thiazolidin-4-one Sulfoxides and Sulfones by S-Oxidation with Oxone

Cannon

Alkurdi

Himel

et al. 2015

IJC

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Abstract1,3-thiazolidin-4-ones, also known as thiazolidin-4-ones, are known to have a very wide range of biological activity. The corresponding S-oxides may show enhanced activity, and therefore viable synthetic routes to these S-oxides are required. S-oxidation of 3-cyclohexyl-2-phenyl-1,3-thiazolidin-4-ones with Oxone ® was investigated. For all compounds evaluated, selective oxidation to the sulfoxide was realized using 3 equivalents of Oxone ® at room temperature. Alternatively, the sulfone was prepared selectively at high temperature by increasing the equivalents of Oxone ® used; the extent of this selectivity was affected by the substituent of the aromatic ring. In those cases in which the reaction produced a mixture of the sulfoxide and sulfone, the ratio of the products was quantified by 1 H NMR.

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Catalyst-free approach for solvent-dependent selective oxidation of organic sulfides with oxone

Cited by 165 publications

References 70 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

Metal-free chemoselective oxidation of sulfides to sulfoxides catalyzed by immobilized taurine and homotaurine in aqueous phase at room temperature

Selective Synthesis of Ortho-substituted 3-Cyclohexyl-2-phenyl-1,3-thiazolidin-4-one Sulfoxides and Sulfones by S-Oxidation with Oxone

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