Selective Oxidation of Sulfides to Sulfoxides using H2O2 Catalyzed by p-Toluenesulfonic Acid (p-TsOH) Under Solvent-Free Conditions

Abstract

An efficient, chemoselective, and environmental friendly procedure for the oxidation of sulfides to sulfoxides is described. Various types of aromatic and aliphatic sulfides are selectively oxidized to sulfoxides in good to excellent yields using 30% H₂O₂ in the presence of catalytic amounts of a p-TsOH under solvent-free conditions at room temperature.     

Mild and Efficient Deoxygenation of Sulfoxides to Sulfides with Cp2TiCl2/Gallium System

The Cp₂TiCl₂/Ga system was found to be a new reagent for reducing a variety of sulfoxides to the corresponding sulfides in good to excellent yields under mild conditions.      

Polyvinylpyrrolidone-Supported Hydroperoxide for Selective Oxidation of Aldehydes to Carboxylic Acids and Sulfides to Sulfoxides

The facile immobilization of hydroperoxide on the cross-linked poly(vinylpyrrolidone) is described by treatment of a poly(vinylpyrrolidone)-Vilsmeier adduct with (35%) hydrogen peroxide. The in situ–generated poly(vinyl pyrrolidone)-supported hydroperoxide reagent showed very good performance in chemoselective oxidation of aldehydes to carboxylic acids as well as sulfides to sulfoxides.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.     

Sulfonated Condensed Polynuclear Aromatic (S-Copna) Resin Catalyzed Selective Oxidation of Sulfides to Sulfoxides or Sulfones Using Hydrogen Peroxide

Abstract

Sulfonated condensed polynuclear aromatic (S-COPNA) resin was found to be a highly efficient, environmentally friendly, recyclable heterogeneous catalyst for the oxidation of alkyl and aryl sulfides to the corresponding sulfoxides or sulfones, in good yields under mild reaction conditions using 30% hydrogen peroxide as an oxidant.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental resource: Synthesis of the S-COPNA resin catalyst. Spectroscopic data for compounds.     

Selective and Efficient Deoxygenation of Sulfoxides with NbCl5/Indium System

It has been found that dialkyl, diaryl, and aryl alkyl sulfoxides can be selectively converted to the corresponding sulfides with a NbCl₅/In system in good to excellent yields under mild conditions. Several functional groups (bromo, chloro, methoxy, aldehyde, and vinyl) were tolerated under the reaction conditions.

Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.     

Selective and Efficient Oxidation of Sulfides to Sulfoxides Using Ceric Ammonium Nitrate (CAN)/Brönsted Acidic Ionic Liquid

A selective and efficient procedure for the oxidation of sulfides to the corresponding sulfoxides is reported using ceric ammonium nitrate in the presence of methylimidazolium hydrogensulfate as Brönsted acidic ionic liquid ([Hmim]HSO ₄ ) as the solvent under mild conditions. The use of nontoxic and inexpensive materials, straightforward procedure, short reaction times, and good yields of the products are the major advantages of this method.     

聚 (4-乙烯基吡啶硝酸盐)、硅硫酸和溴化铵催化氧化硫化物生成亚砜

 A new catalytic procedure for the chemoselective oxidation of sulfides to sulfoxides was studied. A variety of aliphatic and aromatic sulfides were subjected to sulfoxidation by combining poly(4-vinyl pyridinium nitrate), silica sulfuric acid (SiO₂-OSO₃H), and catalytic amounts of ammonium bromide in CH₂Cl₂ in the presence of a few drops of water at room temperature. Excellent yields were obtained.     

Immediate Oxidation of Sulfides to Sulfoxides with Zinc Dichromate Trihydrate under Solvent Free Condition

Various types of sulfides were converted to sulfoxide by zinc dichromate trihydrate in high yields and rates under solvent-free conditions.     

A Novel Catalytic Method for the Oxidation of Sulfides to Sulfoxides with Silica Sulfuric Acid and Sodium Nitrite in the Presence of KBr and/or NaBr as Catalyst

Highly efficient selective oxidation of sulfides to sulfoxides by NaNO₂ and silica sulfuric acid catalyzed with KBr or NaBr has been reported. This oxidation was carried out in the presence of wet SiO₂ (50% w/w) in acetonitrile at room temperature with good to excellent yields.     

Selective Oxidation of Sulfides to Sulfoxides/Sulfones by 30% Hydrogen Peroxide

Abstract

A selective and efficient procedure for the oxidation of various sulfides with sodium tungstate dihydrate with 30% hydrogen peroxide in the presence of trioctylmethylammonium dihydrogen phosphate, respectively, to the corresponding sulfoxides and sulfones is reported. The oxidation reaction is carried out at –5 to 0 °C in the presence of hydroxypropyl-β-cyclodextrins for sulfoxides or at 50–60 °C for sulfones. The mild reaction conditions, easy workup, and good yields of the products are the major advantages of this method.     

A Clean,Mild, and Selective Oxidation of Sulfides to Sulfoxides Using NaClO/H2SO4 in Aqueous Media

A range of sulfides can be selectively oxidized to the corresponding sulfoxides in good yields using NaClO/H₂SO₄ in both water and 50:50 water:EtOH as solvent. Two new compounds are reported that show a diastereoselective oxidation in 2-phenylthioalcohols with possible neighboring hydroxyl group participation with a logic proposed mechanism.     

溴化钾催化硫化物、硝酸铵和 SiO2-OSO3H 固体酸的氧化反应

A convenient and selective catalytic method for the sulfoxidation of aliphatic and aromatic sulfides by treatment of NH4NO3, silica sulfuric acid, wet SiO2 (50% w/w) and a catalytic amount of KBr in CH2Cl2 at room temperature was developed. Many sulfides can be selectively oxidized at room temperature in good to excellent yields. The reaction proceeds without over-oxidation to sulfones under mild conditions.     

Selective Oxidation of Sulfides to Sulfoxides With Poly[4‐Hydroxy(tosyloxy)iodo]styrene

Sulfides can be selectively converted to corresponding sulfoxides in excellent yields under mild conditions by linear and 1% cross‐linked poly[4‐hydroxy(tosyloxy)iodo]styrene (PSHTIB).     

杂多酸催化环己烯氧化合成己二酸

催化氧化;过氧化氢杂多酸;杂多酸催化环己烯氧化合成己二酸     

Mild and Efficient Deoxygenation of Sulfoxides to Sulfides Using HfCl4/KBH4 System

HfCl₄/KBH₄ was found to be a facile, efficient, convenient, and chemoselective system for the deoxygenation of dialkyl, diaryl, and aryl alkyl sulfoxides, especially for the reduction of dibenzyl sulfoxide to the corresponding sulfides under mild conditions. In addition, the HfCl₄/KBH₄ system could be used in reduction of some other sulfur-bearing substrates to the corresponding sulfides, such as 2,2′-dibenzothiazolyl disulfide, but this reducing system could not reduce sulfolane, diphenyl sulfone, p-toluenesulfonic acid, and p-toluenesulfonyl chloride to their corresponding thiophenols.     

含2-三氟甲基苯并咪唑的双噁二唑硫醚及其亚砜衍生物的合成

芳甲酰肼和氯乙酸在二甲苯中反应生成了一系列的2-芳基-5-氯甲基-1,3,4-噁二唑(1a～1j), 继而与2-(2-三氟甲基苯并咪唑-1-亚甲基)-5-巯基-1,3,4-噁二唑(2)在乙醇-水的溶液中反应得到了一系列的含2-三氟甲基苯并咪唑的双噁二唑硫醚3a～3j, 再用硝酸氧化得到相应的亚砜衍生物4a～4j. 化合物的结构经元素分析, IR, ¹H NMR确证.     

Ion Exchange Resin Catalyzed Selective Oxidation of Sulfides to Sulfoxides Using Hydrogen Peroxide

Summary. An efficient method for the selective oxidation of sulfides to sulfoxides under mild and environmentally safe conditions is achieved using hydrogen peroxide in the presence of Amberlyst 15 and Amberlite IR-400 at room temperature. This procedure can be applied for dialkyl and diaryl sulfides with a variety of functional groups. Functional groups such as hydroxyl, methoxy, amino, aldehyde, and olefinic double bonds remain intact.     

Environmentally Benign Oxidation of Some Organic Sulfides with 34% Hydrogen Peroxide Catalyzed by Simple Heteropolyoxometalates

An environmentally benign oxygenation protocol was developed for selective oxidation of some types of aromatic and aliphatic sulfides in good to excellent yields utilizing 34% hydrogen peroxide catalyzed by simple heteropolyoxometalates in normal drinking water at room temperature. The catalysts could be recovered and reused for at least seven reaction cycles under the described reaction conditions without considerable loss of reactivity. This procedure introduced a new insight into the use of simple heteropolyanions as recoverable catalysts for the oxidation of organic sulfides by an environmentally acceptable protocol. Keywords