Deoxygenation Of Sulfoxides Research Articles

Rapid and Efficient Deoxygenation of Sulfoxides with NbCl5/NaI System

However, they often suffer from serious disadvantages, suchas functional group incompatibility, difficult work-up proce-dures, harsh reaction conditions, or not readily availablereagents. Further some of these methods are associated withlimitations regarding low yields and prolonged reactiontimes. Therefore, the search for a new and efficient methodfor the deoxygenation of sulfoxides is still a worthwhilegoal. Particularly much effort has been devoted to thedevelopment of milder conditions where the presence ofvarious sensitive and reducible functional groups can betolerated. The use of low valent oxophilic d-block metals(Zr, Ti, W, Mo) have become important in deoxygenation ofvarious types of organic substrates.

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.

Efficient Organic Transformations Mediated by ZrOCl2·8H2O in Water

Operationally simple and environmentally benign methods for some organic transformations comprising reductive coupling of sulfonyl chlorides, chemoselective deoxygenation of sulfoxides, and halogenation of alcohols mediated by ZrOCl2·8H2O/MX in water have been developed. GRAPHICAL ABSTRACT

Low‐Valent Molybdenum‐Based Dual Pre‐Catalysts for Highly Efficient Catalytic Epoxidation of Alkenes and Deoxygenation of Sulfoxides

AbstractA variety of homoleptic and heteroleptic, triply bonded dimolybdenum hexaalkoxides, [(Mo2(OR)6] and [Mo2(OR)4(OR′)2], were successfully applied as dual pre‐catalysts in both, the epoxidation of olefins with tert‐butyl hydroperoxide and the deoxygenation of diorganosulfoxides with silanes, to form the corresponding sulfides. In the epoxidation of cyclooctene, the pre‐catalysts demonstrated an intriguingly high activity, with turnover frequencies (TOFs) of above 60 000 h−1 at elevated temperatures (≈50 °C) and even very high activity at room temperature. Furthermore, using [Mo2(OtBu)6] as a pre‐catalyst, we studied the effect of the solvent and we extended the epoxidation reaction to more demanding olefins, which revealed a particularly high activity even towards primary alkenes. In addition, the same pre‐catalysts, in comparison to previously reported Mo‐based systems, exhibited excellent activities for the deoxygenation of phenyl methyl sulfoxide to thioanisole in the presence of silanes (TOFs>160 h−1). A number of other diorganosulfoxides were used in the catalytic deoxygenation to investigate the scope and limitations of the system, displaying an excellent performance for differently substituted substrates.

ChemInform Abstract: TAPC‐Promoted Oxidation of Sulfides and Deoxygenation of Sulfoxides.

AbstractTreatment of sulfides with H2O2 and TAPC allows rapid, efficient, and selective access to either sulfoxides or sulfones.

Reduction of sulfoxides catalyzed by oxo-complexes

This work reports the catalytic activity of the oxo-complexes HReO 4, MoO 2(acac) 2, WO 2Cl 2, and VO(acac) 2 in the reduction of sulfoxides with PhSiH 3 or HBcat. The results obtained showed that the catalyst systems PhSiH 3/HReO 4 (5 mol %) and HBcat/HReO 4 (5 mol %) are highly efficient for the deoxygenation of sulfoxides. The complex MoO 2(acac) 2 was also efficient, but the reactions required more time and heating. Finally, the complexes WO 2Cl 2 and VO(acac) 2 showed a moderate activity.

TAPC-Promoted Oxidation of Sulfides and Deoxygenation of Sulfoxides

1,3,5-Triazo-2,4,6-triphosphorine-2,2,4,4,6,6-tetrachloride (TAPC) was found to be an efficient promoter for the oxidation of sulfides and deoxygenation of sulfoxides. Excellent yields, short reaction time, easy and quick isolation of the products, solvent-free process, and excellent chemoselectivity are the main advantages of this procedure.

Nickel Boride

Nickel boride (Ni2B), first reported in the pioneering work of Schlezinger and Brown [¹] and traditionally used as a catalyst for hydrogenation, [²] has more recently found a niche as a reducing agent in its own right. [³] Its ease of preparation, handling, and versatility as a reducing agent promise nickel boride its deserved attention from academic and industrial sectors. Nickel boride has been employed for a wide range of transformations including reductive dehalogenation of organic halides [4] , reductive amination of carbonyl compounds, [5] desulfurization of a variety of thioxo compounds, [6] deoxygenation of sulfoxides and selenoxides, [7] and reducing of nitrogen functionalities. [8] Of late, the reagent is being explored in the form of a nickel boride silica nanocomposite catalyst for hydrogen production from NaBH4 hydrolysis. [9]

ChemInform Abstract: Reductive Dimerization of Sulfonyl Derivatives (I) to Disulfides (II) and Deoxygenation of Sulfoxides (IV) to Sulfides (V) Using the Boron Triiodide - N,N-Diethylaniline Complex.

ChemInform Abstract: Reductive Dimerization of Sulfonyl Derivatives (I) to Disulfides (II) and Deoxygenation of Sulfoxides (IV) to Sulfides (V) Using the Boron Triiodide - N,N-Diethylaniline Complex.

ChemInform Abstract: Structure and Reactivity of Nitroso Oxides.

The presence of nitroso oxide intermediates has been studied in the photooxidation of phenyl azide. The hydroxylation of benzenes occurred and was accelerated by electron-donating groups. Sulfides were oxidized to sulfoxides, but the oxygenation and deoxygenation of sulfoxides proceeded concurrently; these reactions were facilitated by electron-donating substituents. Trapping of the intermediates by added nitrosobenzenes was most efficient, approaching 80% O transfer. The relative reactivity order (styrenes, PhN=O>>Ph 2 S>Ph 2 SO>PhH), substituent effects, and the stereochemistry of hydroxylation of C-H bonds characterized the electrophilic radical nature of nitroso oxides. An 18 O-tracer study revealed that a unimolecular isomerization of nitroso oxides to nitro compounds proceeds competitively with the O transfers; The reactivity of XOO species is discussed on the basis of electronegativity of X

ChemInform Abstract: Chemistry of Cephems: C-4 Substitution and Sulfoxide Deoxygenation Reactions.

ChemInform Abstract: Chemistry of Cephems: C-4 Substitution and Sulfoxide Deoxygenation Reactions.

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.

ChemInform Abstract: Rapid and Mild Deoxygenation of Sulfoxides with MoCl5/Gallium System under Ultrasonication.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Rapid and Mild Deoxygenation of Sulfoxides with MoCl5/Gallium System under Ultrasonication

However, many of these transformations often suffer from serious disadvantages, such as functional group incompati-bility, difficult work-up procedures, or harsh reaction condi-tions. Further some of these methods are associated with limi-tations regarding low yields and long reaction times. Therefore, there still exists a search for new improved methods. Particularly much effort has been devoted to the development of milder conditions where the presence of various sensitive and reducible functional groups can be tolerated. The use of low valent oxophilic d-block metals have become impo rtant in deoxygena-tion of various types of organic substrates.

Mild and Efficient Deoxygenation of Sulfoxides to Sulfides with Triflic Anhydride/Potassium Iodide Reagent System

It was found that the combination of triflic anhydride/potassium iodide was an effective promoter for the deoxygenation of sulfoxides and gave the corresponding sulfides in excellent yield in acetonitrile at room temperature. It is worth mentioning that this reagent system is chemoselective and tolerates various functional groups, such as alkene, ketone, ester, aldehyde, acid, and oxime.

Microwave Assisted Rapid, Efficient and Chemoselective Deoxygenation of Sulfoxides to Thioethers Using Zn / AcOH on Silica Gel

Zn / AcOH on silica gel converts a range of structurally different sulfoxides to their corresponding thioethers in excellent yields under microwave irradiation. It has been found that chemoselective deoxygenation of sufoxides can be achieved in the presence of other reducible functional groups such as acetals, acids, amides, esters, ketones and nitriles.

ChemInform Abstract: Mild and Efficient Deoxygenation of Sulfoxides with a WCl6/Indium System.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Silica—PSCl3: A Mild and Efficient Reagent for Deoxygenation of Sulfoxides.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: A Novel Method for the Deoxygenation of Sulfoxides with the PPh3/Br2/CuBr System.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Mild and Efficient Deoxygenation of Sulfoxides with MoCl5/Indium System.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.