Facile oxidation of sulfides to sulfoxides using iodosobenzene and benzeneseleninic acid as a catalyst

Roh, Kyoung Rok; Kim, Kyoung Soo; Kim, Young Hae

doi:10.1016/s0040-4039(00)74888-x

Cited by 59 publications

(17 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Sulfoxides are usually deemed not to be nucleophilic enough to react with this type of reagents. [49] Sulfinamides seem to be in between. We did not pursue the study further because the yields are similar, but the reagent is more difficult to obtain and leads to the formation of an additional by-product (methyl p-toluenesulfonate), which has to be removed from the reaction mixture.…”

Section: Resultsmentioning

confidence: 99%

Iodine(III)‐Mediated Preparations of Nitrogen‐Containing Sulfur Derivatives: Dramatic Influence of the Sulfur Oxidation State

Leca

Song

Amatore

et al. 2004

Chemistry A European J

View full text Add to dashboard Cite

Reaction of sulfonamides with iodosobenzene leads to phenyliodinanes. A new catalysis reaction of the decomposition of these products in the presence of sulfoxides that allows the smooth synthesis of sulfoximines has been evidenced and studied: copper(II) salts were used to prepare compounds 4 a-j and 5 b, d, f, j, k from the corresponding, easily prepared, sulfoxides. The reactions proceed with retention of configuration at the sulfur center, and copper(II) triflate is the best candidate for the catalyst for the imination. Switching from sulfonamides to sulfinamides in the preparation of the starting iodinanes completely alters the reaction pathway: iodinanes are no longer accessible, and sulfonimidates 7 a-j are obtained instead. This behavior can be rationalized by the increase in pK(a) brought about by the removal of one oxygen atom from the sulfur center. Sulfonimidates are interesting molecules with varied applications. Optimization of their one-pot synthesis has been achieved by carrying out the reaction in acetonitrile. The stereochemical study has shown that the transformation proceeds with global retention of the configuration at the sulfur center, albeit with erosion of the enantiomeric purity. A model accounting for this outcome is proposed. In addition, the presence of oxidized sulfonamide by-products has been explained, and this latter pathway becomes the sole one when alcohol is replaced by water. Good yields of the oxidized products are obtained.

show abstract

Section: Resultsmentioning

confidence: 99%

Iodine(III)‐Mediated Preparations of Nitrogen‐Containing Sulfur Derivatives: Dramatic Influence of the Sulfur Oxidation State

Leca

Song

Amatore

et al. 2004

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…The observed low negative reaction constant, ρ may be visualized due to the neutralization of positive charge on sulfur atom as a result of ligand coupling with oxygen atom. Such a ligand coupling pathway has already been suggested by the researchers in the PA catalysed Cr(VI) oxidation of organic sulfur compounds [12,50]. The intermediate, C 3 then cleaves at α-β position to eliminate CO 2 followed by oxygen atom transfer to sulfur in fast steps leading to the formation of the product, methylphenyl sulfone.…”

Section: Discussionmentioning

confidence: 77%

Picolinic acid promoted oxidative decarboxylation of phenylsulfinylacetic acid by Cr(VI)

Subramaniam¹,

Selvi²

2016

Bull. Chem. Soc. Eth.

View full text Add to dashboard Cite

ABSTRACT. The kinetics and mechanism of picolinic acid promoted reaction of phenylsulfinylacetic acid (PSAA) with Cr(VI) was carried out in aqueous acetonitrile medium under pseudo first order conditions. The reaction follows Michaelis-Menten type of kinetics with respect to PSAA. The catalytic activity by picolinic acid can be interpreted on the basis of the formation of a highly active oxidizing species, Cr(VI)-PA complex. The mechanism involves the formation of a termolecular complex, Cr(VI)-PA-PSAA by the nucleophilic attack of the sulfur atom of PSAA on chromium of Cr(VI)-PA complex in an equilibrium step followed by ligand coupling in a slow step. Electron releasing substituents in the phenyl ring of PSAA accelerate while electron withdrawing groups retard the reaction rate. The overall rate constants for the para-and meta-substituted PSAAs are found to correlate excellently with Hammett σ constants with a very low reaction constant, ρ. .

show abstract

“…Using NaOCl as an oxidant, TEMPO-linked metalloporphirines have been shown to be efficient catalysts in selective oxidation of sulfides to sulfoxides [71]. Iodosobenzene has emerged as an efficient oxidizing agent for the oxidation of unsaturated or otherwise sensitive sulfides to corresponding sulfoxides [72,73]. Iodoxybenzoic acid (IBX)-tetraethyl ammonium bromide has also been shown to be efficient oxidantcatalyst combination in chemoselective oxidation of numerous sulfides.…”

Section: Halogen Hypohalitesmentioning

confidence: 99%

A Concise Review on Synthesis of Sulfoxides and Sulfones with Special Reference to Oxidation of Sulfides

Kupwade

2019

J. Chem. Rev.

View full text Add to dashboard Cite

A large variety of organosulfur compounds have been shown to having diverse biological effects such as antioxidant effects, anti-inflammatory properties, inhibition of platelet aggregation, reduction of systolic blood pressure, and reduction of cholesterol. Among these, sulfoxides and sulfones show wide and significant applications as commodity chemical in various fields of chemistry. Therefore, synthesis of sulfoxides as well as sulfones has remained a point of attraction for synthetic organic chemists. Among array of methods used to synthesize the sulfoxides or sulfones, oxidation of sulfide is the most convenient way. This review precises chemoselective methods for the synthesis of the sulfoxides as well as sulfones focusing on oxidative protocols. This review will aid researchers to explore and utilise the mentioned protocols for different organic transformations.

show abstract

Facile oxidation of sulfides to sulfoxides using iodosobenzene and benzeneseleninic acid as a catalyst

Cited by 59 publications

References 13 publications

Iodine(III)‐Mediated Preparations of Nitrogen‐Containing Sulfur Derivatives: Dramatic Influence of the Sulfur Oxidation State

Iodine(III)‐Mediated Preparations of Nitrogen‐Containing Sulfur Derivatives: Dramatic Influence of the Sulfur Oxidation State

Picolinic acid promoted oxidative decarboxylation of phenylsulfinylacetic acid by Cr(VI)

A Concise Review on Synthesis of Sulfoxides and Sulfones with Special Reference to Oxidation of Sulfides

Contact Info

Product

Resources

About