- Oxidation of thiols using K2S2O8 in ionic liquid
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A green, straightforward, and novel method for oxidation of thiols to the corresponding disulfides is reported using K2S2O8 in the ionic liquid 1-butyl-3-methylimidazolium bromide [(bmim)Br] at 65-70C. The corresponding disulfides were obtained in excellent yield and short reaction time.
- Hajipour, Abdol R.,Mostafavi, Majid,Ruoho, Arnold E.
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- REDUCTION OF HALONITROBENZENES TO HALOANILINES BY HYDROGEN SULFIDE
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A selective method has been developed for the preparation of haloanilines by the reduction of the corresponding halonitrobenzenes using hydrogen sulfide in the presence of tetraalkylammonium hydroxide.
- Rybakova, I. A.,Shekhtman, R. I.,Prilezhaeva, E. N.,Litvinov, V. P.,Shakhovskoi, G. P.
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- Selective synthesis of organic sulfides or disulfides by solvent exchange from aryl halides and KSCN catalyzed by NiCl2·6H2O
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A method for selective synthesis of symmetric sulfides or disulfides from the reaction of aryl halides with KSCN by solvent exchange is introduced. Aryl halides were selectively converted to the symmetric disulfides or sulfides in high yields when they are treated with KSCN in the presence of NiCl2·6H2O and DMAP at 140?°C in DMF or poly ethylene glycol (PEG-200) respectively.
- Abbasi, Mohammad,Nowrouzi, Najmeh,Latifi, Hadis
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- Facile solvent-free oxidation of thiols mediated by mineral supports
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Oxidation of thiols dispersed without solvent on a weakly basic mineral support was easily performed by heating in air.
- Sainte-Marie, Laurent,Guibe-Jampel, Eryka,Therisod, Michel
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- On the reaction of triaryl trithioarsenites, (ArS)3As, with iodine
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Iodine in dry nonprotic solvents oxidizes triaryl trithioarsenites, (ArS)3 As, to As(III) iodide, AsI3, and disulfides, ArSSAr. The reaction most likely involves arylsulfenyl iodide, ArSI, as an intermediate. With triphenyl and tris(
- Markaki, Maria D.,Ioannou, Panayiotis V.
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- Alumina: An Efficient and Reusable Catalyst for the Oxidative Coupling of Thiols with DMSO
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An inexpensive combination of common laboratory reagents, dimethyl sulfoxide (DMSO) and Chromatographic neutral alumina, gives an efficient, selective, and high-yielding oxidation of aromatic, aliphatic and alicyclic thiols to the corresponding disulfides in excellent yields under relatively mild conditions.
- Hirano, Masao,Yakabe, Sigetaka,Monobe, Hiroyuki,Morimoto, Takashi
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- Ligand-free copper-catalysed direct synthesis of diaryl sulfides and diaryl disulfides in wet poly(ethylene glycol)
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An improved protocol has been developed for the one-pot CuI-catalysed preparation of symmetric diaryl sulfides from their available aryl halides in the presence of thiourea as sulfur transfer agent and in the absence of both ligand and organic solvent. This catalytic system was also used for the high-yielding preparation of diaryl disulfides in the presence of C2Cl6 as oxidant.
- Nowrouzi, Najmeh,Abbasi, Mohammad,Latifi, Hadis
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- A facile, high-yielding method for the conversion of halides to mercaptans
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An efficient, high-yield, one-pot preparation of alkyl and activated aryl mercaptans is presented. The method relies on sodium thiophosphate displacement of the halide, followed by mild hydrolysis of the intermediate phosphorothioate.
- Bieniarz,Cornwell
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- Radical-nucleophilic substitution (SRN1) reactions. Part 7. Reactions of aliphatic α-substituted nitro compounds
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α-Nitrothiocyanates R2C(SCN)NO2 have been prepared by oxidative addition of thiocyanate anion to nitronate anions and undergo SRN1 substitution reactions by loss of thiocyanate with nitronate anions, phenylsulfinate, azide and p-nitro- and p-chloro-benzenethiolates in dipolar aprotic solvents. 2-Nitro-2-thiocyanatopropane and other 2-substituted-2-nitropropanes [Me2C(X)NO2 with X = I, Br, Cl, NO2, PhSO2] react with thiolates by SRN1 reactions and/or redox reactions to give disulfides by a polar abstraction or chain SET (SET2) mechanisms. The products are dependent on the nucleophilicity of the thiolates, the polarisability of the α-substituent, the solvent and the presence of light catalysis, radical traps or strong electron acceptors. 2-Substituted-2-nitropropanes [Me2C(X)NO2 with X = N3, NO2, CN, p-NO2-C6H4-N=N] undergo SRN1 substitutions with thiolates by loss of nitrite. 2-Substituted-2-nitropropanes Me2C(X)NO2 and thiolates only yield disulfides in methanol due to solvation of the nitro groups.
- Al-Khalil,Bowman,Gaitonde,Marley,Richardson
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- Synthesis and 13C NMR spectra of N-substituted para-quinone imines: II. N-arylthio- and N-arylsulfonyl-l,4-benzoquinone imines with enhanced electron-withdrawing character of the quinoid ring
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Introduction of chlorine substituents into quinone imine fragment results in virtually the same variations in the chemical shifts of the quinoid ring carbons both in N-arylthio and N-arylsulfonyl-1,4-benzoquinone imines as compared to the unsubstituted analogs. In both classes of chloro-substituted compounds the effect of substituents in the benzene ring on the character and the range of chemical shifts variations for the carbon signals from the quinoid ring also turned out to be identical. Any differences observed may be due to the change in the geometry of the molecules, in particular, to the increase in the bond angle C=N-S.
- Pirozhenko,Avdeenko,Yusina,Konovalova
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- A novel nickel-catalyzed domino method for the direct synthesis of symmetrical disulfides using potassium 5-methyl-1,3,4-oxadiazole-2-thiolate as a sulfurating reagent
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A simple, one pot, efficient, and novel protocol has been developed for the direct synthesis of symmetrical organic disulfides using a domino reaction between an aryl/alkyl halide and potassium 5-methyl-1,3,4-oxadiazole-2-thiolate in the presence of NiCl2 as catalyst. A variety of symmetrical aryl/alkyl disulfides can be obtained in moderate to excellent yields (up to 95%).
- Soleiman-Beigi, Mohammad,Mohammadi, Fariba
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- An environmentally friendly oxidation of thiols to disulfides by calcium hypochlorite and montmorillonite K10 in hexane
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Aromatic, aliphatic, and alicyclic thiols can be readily oxidized to the disulfides quantitatively by calcium hypochlorite and moist Montmorillonite K10 under mild and neutral conditions.
- Hirano, Masao,Yakabe, Shigetaka,Fukami, Masataka,Morimoto, Takashi
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- CLAY-SUPPORTED REAGENTS IV. A NOVEL COUPLING OF THIOLS INTO DISULPHIDES, VIA THIONITRITE INTERMEDIATES USING A CLAY-SUPPORTED NITROSATION REAGENT.
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Thiols are converted into symmetrical disulphides, under very mild conditions, by bentonite-supported Fe(NO3)3*H2O.
- Cornelis, Andre,Depaye, Nicole,Gerstmans, Andre,Laszlo, Pierre
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- Reactions of arensulfenamides with olefins in the presence of picric acid
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N-(2-and 4-Nitrophenylthio)morpholines in the presence of equimolar amounts of picric acid enter into the reaction of electrophilic sulfenylation of the C=C norbornene bond to give bi-and tricyclic sulfides. With cyclohexene, trans-2-arylthiocyclohexanol are formed.
- Zyk,Beloglazkina,Mamaeva
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- Ni-Catalyzed Cross-Coupling Reaction: The Direct Synthesis of Symmetrical Disulfanes from Aryl and Primary Alkyl Halides
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A novel Ni-catalyzed cross-coupling reaction is introduced for the direct synthesis of diaryldisulfanes and dialkyldisulfanes from aryl halides and primary alkyl halides at normal atmospheric conditions, respectively. This one-pot and domino protocol utilizes only 10 mol% of NiCl2 as a catalyst and morpholin-4-ium morpholine-4-carbo-dithioate as a new, stable, solid, and odorless sulfurating reagent in the presence of ethylene glycol as a cosolvent and bidentate ligand in dimethyl formamide (DMF) at 130°C with good to excellent yields and relatively short time reaction.
- Soleiman-Beigi, Mohammad,Arzehgar, Zeinab
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- Pyridine N-Sulphides. Some Simple N-Arylthiopyridinium Salts and a Possible Source of Arylsulphenium Ions
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N,N'-Dipyridinium disulphide dichloride (1) and 1-(4-nitrophenylthio)pyridinium chloride (5) and its 4-NMe2 derivative (2) have been synthesized and their structures established unambiguously; they undergo nucleophilic attack at sulphur rather than in the
- Abramovitch, Rudolph A.,Miller, Adrian L.,Pilski, Jacek
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- Simple, extremely fast, and high-yielding oxidation of thiols to disulfides
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Results of oxidation of thiols to disulfides with 1,3-dibromo-5,5-dimethyl- hydantoin (DBDMH) are described. A simple addition of 0.20-0.25 mol equivalent of solid DBDMH to thiol in chloroform at room temperature yielded the disulfides in excellent yield. The reaction is extremely fast and gave no other oxidized side products. Copyright Taylor & Francis, Inc.
- Alam, Ashraful,Takaguchi, Yutaka,Tsuboi, Sadao
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- Haloacid/dimethyl sulfoxide-catalyzed synthesis of symmetrical disulfides by oxidation of thiols
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A novel method is developed for the oxidation of thiols to the corresponding disulfides using 20 mol % haloacid (HBr or HI) in combination with dimethyl sulfoxide. A tentative mechanism is proposed for the oxidation. In addition to the advantages of cost-effectiveness, simple processes, and broad functional group tolerance, the exclusive formation of disulfides is the principle reward of this methodology while compared to known methods that further oxidize disulfides to S-oxides and other byproducts.
- Natarajan, Palani,Sharma, Himani,Kaur, Mandeep,Sharma, Pooja
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- Photolysis of Alkyl 4-Nitrobenzenesulfenates. A New and Versatile Method for the Generation of Free Radicals
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The irradiation of alkyl 4-nitrobenzenesulfenates with >300-nm wavelength light in benzene solution results in the homolytic cleavage of the O-S bond.The tertiary alkoxy radicals thus formed undergo β scission to produce carbon-centered free radicals in e
- Pasto, Daniel J.,L'Hermine, Gael
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- A novel copper-catalyzed, one-pot synthesis of symmetric organic disulfides from alkyl and aryl halides: Potassium 5-methyl-1,3,4-oxadiazole-2-thiolate as a novel sulfur transfer reagent
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A new method is reported for the synthesis of symmetric diaryl and dialkyl disulfides from aryl and alkyl halides in the presence of copper using potassium 5-methyl-1,3,4-oxadiazole-2-thiolate as the base, ligand, and sulfur-transfer reagent.
- Soleiman-Beigi, Mohammad,Mohammadi, Fariba
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- Formation and Cleavage of Aromatic Disulfide Radical Anions
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The electron transfer (ET) to a series of para-substituted diaryl disulfides, having the general formula (X-C6H4S-) 2, has been studied. The X groups were selected as to have a comprehensive variation of the substituent effect, being X = NH2, MeO, H, F, Cl, CO2Et, CN, and NO2. The reduction was carried out experimentally, using N,N-dimethylformamide as the solvent, and by molecular orbital (MO) ab initio calculations. The ET was studied heterogeneously, by voltammetric reduction and convolution analysis, and homogeneously, by using electrogenerated radical anions as the solution electron donors. The reduction is dissociative, leading to the cleavage of the S-S bond in a stepwise manner. Both experimental approaches led us to estimate the E° and the intrinsic barrier values for the formation of the radical anions. Comparison of the independently obtained results allowed obtaining, for the first time, a quantitative description of the correlation between heterogeneous and homogeneous rate constants of ETs associated with significant inner reorganization energy. The experimental outcome was fully supported by the theoretical calculations, which provided information about the disulfide lowest unoccupied MOs (LUMOs) and singly occupied MO (SOMO), the bond dissociation energies, and the most significant structural modifications associated with radical anion formation. With disulfides bearing electron-donating or mildly electron-withdrawing groups, the inner reorganization is particularly large, which reflects the significant stretching of the S-S bond experienced by the molecule upon ET. The process entails formation of loose radical anion species in which the SOMO is heavily localized, as the LUMO, onto the frangible bond. As a consequence of the formation of these σ*-radical anions, the S-S bond energy of the latter is rather small and the cleavage rate constant is very large. With electron-withdrawing groups, the extent of delocalization of the SOMO onto the aryl system increases, leading to a decrease of the reorganization energy for radical anion formation. Interestingly, while the LUMO now has π* character, the actual reduction intermediate (and thus the SOMO) is still a σ*-type radical anion. With the nitro-substituted disulfide, very limited inner reorganization is required and π*-radical anion initially forms. A nondissociative type intramolecular ET then ensues, leading to the formation of a new radical anion whose antibonding orbital has similar features as those of the SOMO of the other diaryl disulfides. Therefore, independently of the substituent, the actual S-S bond cleavage occurs in a quite similar way along the series investigated. The S-S bond cleavage rate, however, tends to decrease as the Hammett σ increases, which would be in keeping with an increase of both the electronic and solvent reorganization energies.
- Antonello, Sabrina,Daasbjerg, Kim,Jensen, Henrik,Taddei, Ferdinando,Maran, Flavio
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- A novel dual-nano assisted synthesis of symmetrical disulfides from aryl/alkyl halides
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Here, we have reported a novel approach towards dual-nano assisted synthesis of disulfides from coupling of alkyl/aryl halides and sulfur nanoparticles. The indium oxide nanoparticles as catalyst expedite the conversion and sulfur nanoparticle notably enhances the miscibility, providing a faster, high yielding and cost-effective process in ethanol-water system. The method has synthetic advantages in terms of mild reaction framework, catalyst regeneration, and absence of any sulfide or polysulfide linkage as by-product leading to a column free synthesis. A variety of alkyl, aryl and heteroaryl symmetrical disulfides are obtained in good to excellent yields up to exceeding 98%.
- Devi, Namita,Hazarika, Sukanya,Gogoi, Prasanta,Barman, Pranjit
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- Benzyltriphenylphosphonium Peroxodisulfate (PhCH2PPh3)2S2O8: A Mild and Inexpensive Reagent for Efficient Oxidation of Organic Compounds under Nonaqueous and Aprotic Conditions
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Benzyltriphenylphosphonium peroxodisulfate is an easily prepared and stable reagent. It could be used as an oxidant under aprotic and nonaqueous conditions in organic solvents. This reagent oxidizes different classes of alcohols to carbonyl compounds, thiols to disulfides, sulfides to sulfoxides, oximes to carbonyl compounds and aromatic amines to azo compounds efficiently. α-Hydroxy carboxylic acids and phenylacetic acids undergo oxidative decarboxylation to produce carbonyl compounds.
- Mohammadpoor-Baltork, Iraj,Hajipour, Abdol Reza,Mohammadi, Hasan
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- Easy and rapid method for disulfide syntheses using nanophase-manganese (VII) oxide coated clay
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Disulfide bond formation by the oxidation of several thiol compounds using nanophase manganese (VII) oxide coated clay (NM7O coated clay) in chlorinated, nonchlorinated (toluene), and polar solvents (water) is described. During the process, nitro and methoxy groups remain unaffected. The NM7O coated clay is easily prepared, stable, and inexpensive to manufacture. Furthermore, this and other studies prove that NM7O coated clay properties, i.e., mineralogy, chemical, and reactivity, are different from KMnO4. This rapid and facile synthesis coupled with the use of the recyclable NM7O coated clay catalyst will save energy due to low temperature and rapid reaction times, as well as minimal disposal problems, thus decreasing production costs.
- Gondi, Sudershan R.,Son, David Y.,Biehl, Edward R.,Vempati, Rajan K.
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- A nickel nanoparticle engineered CoFe2O4/SiO2-NH2@carboxamide composite as a novel scaffold for the oxidation of sulfides and oxidative coupling of thiols
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The purpose of this work was to prepare a new Ni-carboxamide complex supported on CoFe2O4 nanoparticles (CoFe2O4/SiO2-NH2@carboxamide-Ni). The carboxamide host material unit generated cavities that stabilized the nickel nanoparticles effectively and preve
- Zohrevandi, Mina,Mozafari, Roya,Ghadermazi, Mohammad
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- Novel method for preparation of symmetric disulfides from thiols using enzyme catalysis
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Mild and efficient method for preparation of variety of symmetric disulfides from oxidation of thiols using horseradish peroxidase or mushroom tyrosinase as catalyst is described.
- Sridhar,Kumara Vadivel,Bhalerao
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- Semisynthetic enzymes in asymmetric synthesis: Enantioselective reduction of racemic hydroperoxides catalyzed by seleno-subtilisin
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The serine protease subtilisin was chemically converted into the peroxidase-active seleno-subtilisin. This semisynthetic enzyme catalyzes the enantioselective reduction of racemic hydroperoxides in the presence of thiophenols to yield optically active hydroperoxides and alcohols on the semipreparative scale. The kinetic parameters and enantioselectivities of seleno-subtilisin-catalyzed reduction of various chiral hydroperoxides were determined. The catalytic efficiency of this semisynthetic enzyme is comparable to that of the native horseradish peroxidase. The sense in the enantioselectivity of the seleno-subtilisin is opposite to the natural enzymes previously used in the synthesis of optically active hydroperoxides. Consequently, the semisynthetic enzyme selenosubtilisin complements the naturally available peroxidases for the asymmetric synthesis of both enantiomers.
- Haering, Dietmar,Schueler, Ellen,Adam, Waldemar,Saha-Moeller, Chantu R.,Schreier, Peter
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- A novel method for the syntheses of symmetrical disulfides using CsF-Celite as a solid base
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The oxidative coupling of aliphatic, aromatic and heteroaromatic thiols to disulfides using cesium fluoride-Celite is described. CsF-Celite provides an efficient, convenient and practical method for the syntheses of symmetrical disulfides.
- Shah, Syed Tasadaque A.,Khan, Khalid M.,Fecker, Miriam,Voelter, Wolfgang
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- Oxidation of thiols to bisulfides using silica chloride as a heterogeneous catalyst
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Silica chloride is used as a selective and effective heterogeneous catalyst for the rapid conversion of thiols to disulfides with quantitative yields in a very short period of time. Copyright
- Sathe, Manisha,Ghorpade, Ramarao,Kaushik, Mahabir Parshad
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- The direct synthesis of symmetrical disulfides and diselenides by metal-organic framework MOF-199 as an efficient heterogenous catalyst
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A highly crystalline porous copper-based metal-organic framework MOF-199 was synthesized, and characterized by several techniques, including XRD, EDX, SEM, and FT-IR. MOF-199 was used as an efficient catalyst for the one-pot and efficient synthesis of organic dichalcogenides from aryl halides (-OTs) and elemental sulfur and selenium in polyethylene glycols (PEGs). A variety of disulfides and diselenides can be obtained in good to excellent yields of up to 98% in a relatively short reaction time.
- Soleiman-Beigi, Mohammad,Yavari, Issa,Sadeghizadeh, Fatemeh
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- A mild and efficient protocol for oxidation of thiols to disulfides in water
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A novel vanadium polyoxometalate [(C7H7)(CH 3)3N]3[H3V10O 28].3H2O works as a useful oxidant for the oxidation of thiols to disulfldes in water under mild reaction conditions in an excellent yield.
- Dewan, Anindita,Bora, Utpal,Kakati, Dilip K.
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- Oxidation by Chemical Manganese Dioxide. Part 2.1 Simple and High-yielding Synthesis of Symmetrical Disulfides via the Oxidative Coupling of Thiols
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Aromatic, aliphatic, and alicyclic thiols readily underwent oxidative coupling with chemical manganese dioxide in hexane to afford the corresponding disulfides in essentially quantitative yields under relatively mild conditions.
- Hirano, Masao,Yakabe, Sigetaka,Chikamori, Hideki,Clark, James H.,Morimoto, Takashi
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- Microwave-assisted, metal- and solvent-free synthesis of diaryl thioethers from aryl halides and carbon disulfide in the presence of [DBUH]+[OAc]-
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A microwave-assisted direct coupling between aryl halides and carbon disulfide in ionic liquid [DBUH]+[OAc]- (DBU = 1,8-diazabicyclo-[5.4.0] undec-7-ene) has been developed. The reactions are very efficient, affording the corresponding diaryl thioethers in moderate to high yields. Aryl chlorides could also be reacted with carbon disulfide using this protocol. Moreover, [DBUH]+[OAc]- could be easily recovered and reused for several runs.
- Zhou, Yongsheng
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- A supramolecular microgel glutathione peroxidase mimic with temperature responsive activity
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Glutathione peroxidase (GPx) protects cells from oxidative damage by scavenging surplus reactive oxygen species (ROS). Commonly, an appropriate amount of ROS acts as a signal molecule in the metabolism. A smart artificial GPx exhibits adjustable catalytic activity, which can potentially reduce the amount of ROS to an appropriate degree and maintain its important physiological functions in metabolism. To construct an optimum and excellent smart artificial GPx, a novel supramolecular microgel artificial GPx (SM-Te) was prepared based on the supramolecular host-guest interaction employing the tellurium-containing guest molecule (ADA-Te-ADA) and the cyclodextrin-containing host block copolymer (poly(N-isopropylacrylamide)-b-[polyacrylamides-co-poly(6-o-(triethylene glycol monoacrylate ether)-β-cyclodextrin)], PPAM-CD) as building blocks. Subsequently, based on these building blocks, SM-Te was constructed and the formation of its self-assembled structure was confirmed by dynamic light scattering, NMR, SEM, TEM, etc. Typically, benefitting from the temperature responsive properties of the PNIPAM scaffold, SM-Te also exhibited similar temperature responsive behaviour. Importantly, the GPx catalytic rates of SM-Te displayed a noticeable temperature responsive characteristic. Moreover, SM-Te exhibited the typical saturation kinetics behaviour of a real enzyme catalyst. It was proved that the changes of the hydrophobic microenvironment and the pore size in the supramolecular microgel network of SM-Te played significant roles in altering the temperature responsive catalytic behaviour. The successful construction of SM-Te not only overcomes the insurmountable disadvantages existing in previous covalent bond crosslinked microgel artificial GPx but also bodes well for the development of novel intelligent antioxidant drugs. This journal is the Partner Organisations 2014.
- Yin, Yanzhen,Jiao, Shufei,Lang, Chao,Liu, Junqiu
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- Natural gallic acid catalyzed aerobic oxidative coupling with the assistance of MnCO3 for synthesis of disulfanes in water
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The formation of S-S bonds has great significance and value in synthetic chemistry and bioscience. To pursue a sustainable approach for such a synthesis, an aerobic oxidative coupling method for the efficient preparation of organic disulfanes, using a low-toxic natural gallic acid as an organocatalyst, inexpensive MnCO3 as a cocatalyst, O2 as the terminal oxidant and water as the solvent, has been successfully developed. Such metal-organic cooperative catalytic protocol provided an access to various symmetrical and unsymmetrical disulfanes in up to 99% yield. Gram scale synthesis with practical convenience and low loading of catalysts further illustrates the practicability of our method.
- Song, Lijuan,Li, Wenhao,Duan, Wenxue,An, Jichao,Tang, Shanyu,Li, Longjia,Yang, Guanyu
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- Unsymmetrical Disulfide Synthesis through Photoredox Catalysis
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A facile and eco-friendly visible light-mediated synthesis of symmetrical and unsymmetrical disulfides using tris[2-phenylpyridinato-C2,N]iridium(III) under additive and oxidant free conditions has been disclosed. The developed method is very mild, several functional group tolerant and highly atom economical requiring extremely low amount of catalyst loading (0.5 mol%). (Figure presented.).
- Dethe, Dattatraya H.,Srivastava, Aparna,Dherange, Balu D.,Kumar, B. Vijay
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- Efficient oxidative coupling of thiols into disulfides using N-tert-butyl-N-chlorocyanamide
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Reaction of aliphatic/aromatic/heterocyclic thiols with N-tert-butyl-N-chlorocyanamide in presence of sodium bromide is described. The reaction was very rapid and resulted in the formation of disulfides in excellent yields under mild conditions.
- Kumar, Vinod,Kaushik, Mahabir Parshad
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- Hammett correlations as test of mechanism of CO-induced disulfide elimination from dinitrosyl iron complexes
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The displacement of RS from [(NHC)(SPh)Fe(NO)2] (NHC = N-heterocyclic carbene) by carbon monoxide follows associative kinetics, rate = k [CO]1 [(NHC)(SPh)Fe(NO)2]1, resulting in reduction of the oxidized form of
- Pulukkody, Randara,Kyran, Samuel J.,Drummond, Michael J.,Hsieh, Chung-Hung,Darensbourg, Donald J.,Darensbourg, Marcetta Y.
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- Thiol-Olefin Cooxidation (TOCO) Reaction. 8. Solvent Effects in the Oxidation of Some Thiols with Molecular Oxygen
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The rates of the noncatalytic oxidation of various thiols by molecular oxygen are a function of the chemical environment of the thiol.A relationship between the chemical shifts of the sulfhydryl proton and the rate of oxidation of the given thiol is demonstrated and discussed.
- D'Souza, Valerian T.,Iyer, Vaidyanath K.,Szmant, H. Harry
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- Aryl diazonium salt and thioacetamide: A catalyst free, efficient blend of an inexpensive arylating agent with "s" surrogate for sulphide synthesis
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Novel, facile C-S and S-S bond coupling reactions were achieved by using an aryl diazonium salt as an arylating agent and thioacetamide as a sulphur surrogate. The reaction proceeds smoothly at room temperature without using any transition metal catalyst, ligand or base. Aryl diazonium salts undergo rapid reactions with thioacetamide at room temperature to give the desired products in a much shorter period than the previously reported metal catalysed protocols.
- Bhojane, Jeevan Manohar,Sarode, Sachin Ashok,Nagarkar, Jayashreemilind
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- Photochemistry of nitrobenzenethiol. Selective generation of the thio radical and thione triplet state as a function of solvent polarity
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Transient absorption spectra of p-nitrobenzenethiol (NBSH) have been measured by the nanosecond laser flash photolysis method. In nonpolar and less polar solvents, nitrobenzenethio radical (NBS(·)) was predominantly formed by the homolytic fission of the
- Alam,Ito
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- Construction of starch-based bionic glutathione peroxidase and its catalytic mechanism
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Glutathione peroxidase (GPx) is an important selenium-containing antioxidant enzyme in human body. The preparation of bionic GPx and the mimicry of its catalytic behavior are of great significance for the development of antioxidant drugs. At present, most of the reported biomimetic selenoenzymes based on the macromolecular are difficult to be degraded, which restricts their applications in the fields such as medical treatment, health care, and functional food. In order to solve this issue, herein, the octenyl succinic acid-modified starch (OSA starch) prepared by the esterification of waxy corn starch was used as the raw material, a new selenium-functionalized starch (Se-starch) was synthesized via the reaction of OSA starch and sodium hydrogen selenide. Such Se-starch, as a biomimetic selenoenzyme, was characterized using 1H NMR, EDS, XPS, SEM, XRD, and FT-IR. The Se-starch with a catalytic activity of 2.48?μM·min?1 showed a typical catalysis behavior of saturated kinetic and enzymology. This catalytic activity is 1.04 × 105 times higher than that of the PhSeSePh, a representative small molecule bionic GPx. The study of catalytic mechanism revealed that the octenyl succinate molecule bonded on the starch endowed it with hydrophobic micro-environments, which benefited the binding of hydrophobic substrates, and consequently increased the catalytic activity. This work not only provided a new idea for constructing natural polymers-based bionic GPx, but also offered an important theoretical basis for the development of new antioxidant drugs and functional foods.
- Jiao, Shu-Fei,Liang, Xing-Tang,Liu, Yong-Xian,Liu, Zi-Jie,Yin, Yan-Zhen,Zhang, Rui-Rui,Zheng, Yun-Ying
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- Janus -faced oxidant and antioxidant profiles of organo diselenides
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To date, organoseleniums are pre-eminent for peroxide decomposition and radical quenching antioxidant activities. On the contrary, here, a series of Janus-faced aminophenolic diselenides have been prepared from substituted 2-iodoaniline and selenium powder using copper-catalyzed methodology. Subsequently, condensation with substituted salicylaldehyde afforded the Schiff base, which on reduction, yielded the desired substituted aminophenolic diselenides in 72%-88% yields. The generation of reactive oxygen species (ROS) from oxygen gas by the synthesized aminophenolic diselenides was studied by analyzing the oxidation of dichlorofluorescein diacetate (DCFDA) dye and para-nitro-thiophenol by fluorescence and UV-Visible spectroscopic methods. Furthermore, density functional theory calculations and crystal structure analysis revealed the role of functional amine and hydroxyl sites present in the Janus-faced organoselenium catalyst for the activation of molecular oxygen, where NH and phenolic groups bring the oxygen molecule close to the catalyst by N-H?O and O-H?O intermolecular interactions. Additionally, these functionalities stabilize the selenium-centered radical in the formed transition states. Antioxidant activities of the synthesized diselenides have been explored as the catalyst for the decomposition of hydrogen peroxide using benzenethiol sacrificial co-reductant by a well-established thiol assay. Radical quenching antioxidant activity was studied by the quenching of DPPH radicals at 516 nm by UV-Visible spectroscopy. The structure activity correlation suggests that the electron-rich phenol and electron-rich and sterically hindered selenium center enhance the oxidizing property of the aminophenolic diselenides. Janus-faced diselenides were also evaluated for their cytotoxic effect on HeLa cancer cells via MTT assay, which suggests that the compounds are effective at 15-18 μM concentration against cancer cells. Moreover, the combination with therapeutic anticancer drugs Erlotinib and Doxorubicin showed promising cytotoxicity at the nanomolar concentration (8-28 nM), which is sufficient to suppress the growth of the cancer cells. This journal is
- Batabyal, Monojit,Dutta, Tanoy,Koner, Apurba Lal,Kumar Jha, Raushan,Kumar, Sangit,Upadhyay, Aditya
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supporting information
p. 14576 - 14594
(2021/11/03)
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- Photochemical metal-free aerobic oxidation of thiols to disulfides
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Thiol oxidation to disulfides is an area of great importance in organic synthesis, both for synthetic and biological purposes. Herein, we report a mild, inexpensive and green photochemical approach for the synthesis of both symmetrical and non-symmetrical disulfides, using metal-free and environmentally friendly conditions. Utilizing phenylglyoxylic acid as the photoinitiator, common household bulbs as the light source and a simple inorganic salt as the additive, a versatile oxidation of thiols leading to products in excellent yields is described. This journal is
- Spiliopoulou, Nikoleta,Kokotos, Christoforos G.
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supporting information
p. 546 - 551
(2021/01/28)
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- Copper-catalyzedortho-selective direct sulfenylation ofN-aryl-7-azaindoles with disulfides
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A copper-catalyzed direct C-H chalcogenation ofN-aryl-azaindoles with disulfides is described. This transformation was performed using Earth abundant Cu(OAc)2as a catalyst, benzoic acid as an additive, air as a terminal oxidant, and readily available diaryl and dialkyldisulfides (or diselenide) as chalcogenation reagents. High functional group tolerance and excellent regioselectivity are demonstrated by the efficient preparation of a wide range ofortho-sulfenylation-7-azaindoles.
- Ru-Jian, Yu,Chun-Yan, Zhang,Xiang, Zhou,Xiong, Yan-Shi,Duan, Xue-Min
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supporting information
p. 2901 - 2906
(2021/04/14)
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- Green Aerobic Oxidation of Thiols to Disulfides by Flavin-Iodine Coupled Organocatalysis
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Coupled catalysis using a riboflavin-derived organocatalyst and molecular iodine successfully promoted the aerobic oxidation of thiols to disulfides under metal-free mild conditions. The activation of molecular oxygen occurred smoothly at room temperature through the transfer of electrons from the iodine catalyst to the biomimetic flavin catalyst, forming the basis for a green oxidative synthesis of disulfides from thiols.
- Iida, Hiroki,Kozako, Ryo,Oka, Marina
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supporting information
p. 1227 - 1230
(2021/06/21)
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- Using Solid Catalysts in Disulfide-Based Dynamic Combinatorial Solution- and Mechanochemistry
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It was shown for the first time that solid amines can act as catalysts for disulfide-based dynamic combinatorial chemistry (DCC) by ball mill grinding. The mechanochemical equilibrium for the two disulfide reactions studied was reached within 1–3 h using ten different amine catalysts. This contrasts with the weeks to months to achieve solution equilibrium for most solid amine catalysts at 2 %mol mol?1 concentration in a 2 mMolar disulfide dynamic combinatorial library in a suitable solvent. The final mechanochemical equilibrium was independent of the catalyst used but varied with other ball mill grinding factors such as the presence of traces of solvent. The different efficiencies of the amines tested were discussed.
- Belenguer, Ana M.,Lampronti, Giulio I.,Michalchuk, Adam A. L.,Sanders, Jeremy K. M.
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- Transformation of arylboronic acids with sodium thiosulfate into organodisulfides catalyzed by a recyclable polyoxometalate-based Cr(iii) catalyst
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Organo disulfides represent an abundant class of compounds in chemical biology, pharmaceutical fields, and industry. They are traditionally synthesized by the oxidation of mercaptan in the presence of an organic ligand supported metal catalyst or toxic oxidants under harsh conditions. Here, we disclose a highly-efficient pathway in which disulfide is synthesized by organic boric acid and Na2S2O3 using the catalyst (NH4)3[CrMo6O18(OH)6], demonstrating a high activity and excellent selectivity. Various boric acid derivatives have been successfully transformed into the corresponding disulfides. Mechanistic insights have been furnished based on the observation of intermediate and control experiments.
- Chang, Yalin,Li, Huiyi,Tao, Chaofu,Wang, Aiping,Wei, Yongge,Xie, Ya,Yu, Han,Yu, Shunming
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supporting information
p. 6059 - 6064
(2021/08/23)
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- Substituted o-Aminophenols as Redox-Mediators in the Thiol Oxidation to Unsymmetrical Disulfides
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A number of substituted o-aminophenols has been investigated as redox mediators of the thiol oxidation to disulfides. The electrooxidation of o-aminophenols leads to the corresponding o-iminobenzoquinones. These compounds react with thiols in the solution with a formation of disulfides. It was established that the use of 4,6-di-tert-butyl-2-(tert-butylamino)phenol as a redox mediator can reduce the overpotential of the thiol oxidation by 0.2-1.4 V depending on the nature of the coupling thiols. The unsymmetrical disulfides with alkyl, aryl, and heteroaryl substituents were obtained as the result of the indirect electrosynthesis.
- Berberova, Nadezhda T.,Burmistrova, Daria A.,Galustyan, Andrey,Smolyaninov, Ivan V.
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- Palladium-Catalyzed Picolinamide-Directed Benzylic C(sp3)?H Chalcogenation with Diaryl Disulfides and Diphenyl Diselenide
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The first palladium-catalyzed direct benzylic C(sp3)?H chalcogenation with diaryl disulfides and diphenyl diselenide has been established. The coupling reaction proceeds between the thioether radical and palladiumcycle intermediate. Picolinamide serves as an excellent directing group for the C?H activation of benzylic C(sp3)?H and can be easily removed. The current protocol exhibits a relatively broad substrate scope and high functional group compatibility. A mechanistic study indicates that palladium(IV) intermediate is probably formed during the course of the reaction. (Figure presented.).
- Wang, Kai,Hou, Jiahao,Zhang, Changjun,Cheng, Ke,Bai, Renren,Xie, Yuanyuan
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supporting information
p. 2947 - 2952
(2020/06/17)
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- Method for synthesizing symmetric disulfide compound by taking aryl hydrazine and S8 as raw materials
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The invention relates to a method for synthesizing a symmetric disulfide compound by taking aryl hydrazine and S8 as raw materials, and belongs to the technical field of organic synthesis; the methodis characterized in that the aryl hydrazine compound and S8 are used as substrates to react in a reaction solvent under the promotion of alkali to generate the symmetric disulfide organic compound, the reaction gas atmosphere is air or oxygen, the reaction temperature is 40 DEG C-100 DEG C, and the reaction time is 4-24 hours. The synthesis steps are simple, the reaction conditions are mild, S8 which is widely distributed in nature, low in price and easy to obtain is used as a sulfur source, S-S bonds can be constructed only under the promotion of alkali without transition metal catalysis, theyield is as high as 95%, the applicable reaction substrate range is wide, the operation is simple and feasible, the synthesis cost is low, the environmental pollution is small, and a new thought is provided for the synthesis of the symmetric disulfide organic compound.
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Paragraph 0053-0056
(2020/11/23)
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- Fenton-Inspired C-H Functionalization: Peroxide-Directed C-H Thioetherification
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Substoichiometric iron mediates the thioetherification of unactivated aliphatic C-H bonds directed by resident silylperoxides. Upon exposure to a catalytic amount of iron(II) triflate, TIPS-protected peroxides bearing primary, secondary, and tertiary C-H sites undergo chemoselective thioetherification of remote C-H bonds with diaryl disulfides. The reaction demonstrates a broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic experiments suggest that the reaction proceeds through 1,5-H atom abstraction by a hydroxyl radical generated with iron.
- Groendyke, Brian J.,Modak, Atanu,Cook, Silas P.
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p. 13073 - 13091
(2019/10/10)
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- Natural product inspired allicin analogs as novel anti-cancer agents
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A series of novel analogs of Allicin (S-allyl prop-2-ene-1-sulfinothioate) present in garlic has been synthesized in high yield. Synthesized 23 compounds were evaluated against different breast cancer cells (MDA-MB-468 and MCF-7) and non-cancer cells (WI38). Four compounds (3f, 3h, 3m and 3u) showed significant cytotoxicity against cancer cells whereas nontoxic to the normal cells. Based on the LD50 values and selectivity index (SI), compound 3h (S-p-methoxybenzyl (p-methoxyphenyl)methanesulfinothioate) was considered as most promising anticancer agent amongst the above three compounds. Further bio-chemical studies confirmed that compound 3h promotes ROS generation, changes in mitochondrial permeability transition and induced caspase mediated DNA damage and apoptosis.
- Bhaumik, Ishani,Pal, Kunal,Debnath, Utsab,Karmakar, Parimal,Jana, Kuladip,Misra, Anup Kumar
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p. 259 - 272
(2019/02/07)
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- First use of an organobismuth reagent in C(sp3)–S bond formation: Access to aryl cyclopropyl sulfides via copper-catalyzed S–Cyclopropylation of thiophenols using tricyclopropylbismuth
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The direct S-cyclopropylation of thiophenols using tricyclopropylbismuth is reported. The reaction is catalyzed by copper(II) acetate and operates under mild conditions to afford the corresponding aryl cyclopropyl sulfides in moderate to good yields. This reaction represents the first use of an organobismuth reagent in C(sp3)–S bond formation.
- Benoit, Emeline,Bueno, Bianca,Choinière, Catherine,Gagnon, Alexandre
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supporting information
p. 72 - 77
(2019/05/15)
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- Unsymmetrical Disulfides Synthesis via Sulfenium Ion
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An umpolung approach for the synthesis of unsymmetrical disulfides via sulfenium ion is reported. In situ generated electrophilic sulfenium ion from electron-rich thiols reacted with second thiols to yield unsymmetrical disulfides. Using an iodine catalyst and 4-dimethylaminopyridine (DMAP)/water as promoter, the target syntheses were achieved in one pot under aerobic condition.
- Parida, Amarchand,Choudhuri, Khokan,Mal, Prasenjit
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supporting information
p. 2579 - 2583
(2019/07/15)
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- Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides
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A highly chemoselective, efficient and nano-Pd catalyzed protocol for the rapid construction of sulfoxides and sulfones via the oxidation of symmetrical and unsymmetrical sulfides using H2O2 as an oxidant has been developed, respectively. The ready availability of starting materials, easy recovery and reutilization of the catalyst, wide substrate scope, and high yields make this protocol an attractive alternative. The process also involves the metal-free and microwave-promoted synthesis of symmetrical diarylsulfides, and FeCl3-mediated preparation of symmetrical diaryldisulfides through the reaction of arenediazonium tetrafluoroborates with Na2S·9H2O as a sulfur source. In addition, unsymmetrical sulfides were generated via the K2CO3-mediated reaction of arenediazonium tetrafluoroborates with symmetrical disulfides.
- Li, Xing,Du, Jia,Zhang, Yongli,Chang, Honghong,Gao, Wenchao,Wei, Wenlong
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p. 3048 - 3055
(2019/03/21)
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- Magnetic iron oxide nanoparticles/K2S: a simple and scale-up method for the direct synthesis of symmetrical disulfides from aryl halides
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A simple, one-pot, efficient and novel protocol has been developed for direct synthesis of symmetrical organic disulfides by domino reaction of aryl halides and K2S in the presence of magnetic Fe3O4 nanoparticles as a readily available, highly efficient and recyclable catalyst. A variety of diaryl disulfides can be obtained in good-to-excellent yields up to 98%.
- Soleiman-Beigi, Mohammad,Mohammadi, Keivan,Mohammadi, Fariba
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p. 1545 - 1550
(2018/06/21)
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- A Novel Method for the Direct Synthesis of Symmetrical and Unsymmetrical Sulfides and Disulfides from Aryl Halides and Ethyl Potassium Xanthogenate
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An efficient and new method for the synthesis of disulfides and sulfides via the reaction of aryl halides with ethyl potassium xanthogenate in the presence of MOF-199 is described. O -Ethyl- S -aryl carbonodithioate has a key role as an intermediate in this procedure; it was converted into symmetrical diaryl disulfides in DMF. Additionally, this could be applied to the synthesis of unsymmetrical aryl alkyl(aryl′) disulfides by the reaction with S -alkyl(aryl) sulfurothioates (Bunte salts) as well as unsymmetrical aryl alkyl(aryl′) sulfides in DMSO.
- Soleiman-Beigi,Arzehgar
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supporting information
p. 986 - 992
(2018/02/09)
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- Europhtal (8020) efficiently catalyzes the aerobic oxidation of in situ generated thiols to symmetric disulfides (disulfanes)
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Efficient, odorless and scalable synthetic protocols have been introduced for the preparation of symmetric alkyl disulfides by treatment of the corresponding organic halides with thiourea and NaHCO3in the presence of commercially available Europhtal catalyst (8020) in both H2O and poly ethylene glycol (PEG-200) media at 80–90 °C. Structurally diverse primary, secondary, allylic and benzylic halides were examined successfully whereas, the result with tert-butyl bromide was not satisfactory. Also, another procedure has been introduced for achieving symmetric aryl disulfides in high yields by reacting aryl halides, thiourea and NaHCO3in PEG-200 at 115–120 °C using CuI along with Europhtal catalysts. The results showed that the aerobic oxidation of in situ generated thiols proceeded efficiently in the presence of Europhtal catalyst giving the symmetric disulfide without contamination by symmetric sulfide side-product.
- Abbasi, Mohammad,Sabet, Askar,Sabet, Askar
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- Conversion of organic halides to disulfanes using KCN and CS2
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A sulfur transfer reagent was produced in situ upon stirring a mixture of KCN and CS2 in DMF at r.t. for 15 min, which after heating with an alkyl halide or aryl halide and CuI gave the corresponding symmetric dialkyl or diaryl disulfide, respectively, in high to excellent yields.
- Abbasi, Mohammad,Nowrouzi, Najmeh,Borazjani, Saeedeh Ghassab
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p. 4251 - 4254
(2017/10/11)
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- IF5 affects the final stage of the Cl-F exchange fluorination in the synthesis of pentafluoro-λ6-sulfanyl-pyridines, pyrimidines and benzenes with electron-withdrawing substituents
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A difficult chlorine-fluorine (Cl-F) exchange fluorination reaction in the final stage of the preparation of pentafluoro-λ6-sulfanyl-(hetero)arenes having electron-withdrawing substituents has now been elucidated through the use of iodine pentafluoride. A major side-reaction of C-S bond cleavage was sufficiently inhibited by the potential interaction between F and I with a halogen bonding.
- Cui, Benqiang,Kosobokov, Mikhail,Matsuzaki, Kohei,Tokunaga, Etsuko,Shibata, Norio
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supporting information
p. 5997 - 6000
(2017/07/10)
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- Silver-induced self-immolative Cl-F exchange fluorination of arylsulfur chlorotetrafluorides: Synthesis of arylsulfur pentafluorides
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A novel strategy for the synthesis of arylsulfur pentafluorides by silver carbonate-induced Cl-F exchange fluorination of arylsulfur chlorotetrafluorides is reported. This fluorination does not require any exogenous fluoride sources. Rather, the reaction proceeds via the self-immolation of the substrate Ar-SF4Cl.
- Cui, Benqiang,Jia, Shichong,Tokunaga, Etsuko,Saito, Norimichi,Shibata, Norio
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supporting information
p. 12738 - 12741
(2017/12/06)
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- An efficient domino Cu-mediated access to organic disulfides from aryl/alkyl halides: Sodium thiosulfate used as a sulfurating reagent
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Background: We have developed a one-pot, simple and efficient protocol for the direct synthesis of symmetrical organic disulfides in high yields via domino reaction between aryl/alkyl halides and Sodium thiosulfate as the sulfur source, in the presence of copper/imidazole and K2CO3. Methods: Owing to the importance seen in the synthesis disulfides, as is evident from the number of publications in the recent past, and our continuing interest in the synthesis of organosulfur compounds using direct synthesis and domino reaction. Herein we designed the synthesis of various disulfide using reaction of aryl/alkyl halides with sodium thiosulfate in presence CuI catalyst, K2CO3 and imidazol as ligand in solvent DMSO. The reaction of iodobenzene with sodium thiosulfate was studied under normal atmospheric conditions in order to optimize the reaction conditions in terms of temperature, amount of reagent and catalyst, and the type of ligand. Results: Effect of solvent and ligand was perceptible, The reaction proceeded not well in the absence of a ligand. The best ligand for these reaction was imidazole. The various solvents tested in this investigation. It was observed that excellent yield of the product was obtained when the reaction was carried out by using DMSO as solvent. The reaction no proceeded in the absence of a base. K2CO3 was a good choice. We examined various amount of the copper salt. It was found to be the best choice in presence 0.7 mmol from copper salt. Also it was significantly found that the reaction yield and rate increased with temperature. The reaction favoured at 130°C temperature. The 3 mmol Na2S2O3·5H2O concentration was sufficient to give maximum yield of the required product in comparison with other amounts. Diaryl/alkyl disulfides were synthesized in terms of the connecting and type position of the substituents on the aryl/alkyl groups, so that products with different substituents, both electron withdrawing and electron-donating substituent, were synthesized in the ortho, meta and para positions. The results show that iodobenzene and bromobenzene were effective for the reaction. Although it was seen that the reaction cannot progress with compound of aryl chloride. Symmetrical diheteroaryl disulfides were well synthesized from the corresponding heteroaryl iodides, bromides and chlorides. Conclusion: In summary, we have developed a new and effective method for the direct synthesis of diaryl/alkyl disulfides from various aryl/alkyl halides by domino reaction. In this work reports an effective and cheap metal catalyzed sulfur transfer reaction, which is more economic, and more environmentally friendly and more comprehensive than previous methods. As a novel sulfur source, Na2S2O3 shows notable advantage in this system. This reaction functions under mild conditions, and various functional groups are well tolerated.
- Soleiman-Beigi, Mohammad,Basereh, Ali,Mohammadi, Fariba
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p. 706 - 710
(2017/02/05)
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- Metal Organic Framework 199- Catalyzed Domino Sulfur-Coupling and Transfer Reactions: The Direct Synthesis of Symmetric Diaryl Disulfides from Aryl Halides
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Abstract: A highly porous metal–organic framework Cu3 BTC2 (copper(II)-benzene-1,3,5-tricarboxylate) that known as MOF-199 was synthesized, and characterized by common methods including, FT-IR, XRD, EDX, SEM and then used as an efficient and recyclable catalyst for the direct synthesis of symmetric organic disulfides. A variety of symmetric diaryl disulfides with high chemoselectivity can be obtained by domino reaction of aryl halides (and tosylates) and potassium 5-methyl-1,3,4-oxadiazole-2- thiolate, as the base and sulfur-transfer reagent, in the presence of MOF-199. Graphical Abstract: [Figure not available: see fulltext.]
- Soleiman-Beigi, Mohammad,Mohammadi, Fariba
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p. 1497 - 1504
(2016/07/30)
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- Symmetrical disulfide synthesis via nickel-catalysis using potassium sulfide as sulfur source
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Abstract: An efficient one-pot method for the synthesis of organic disulfides from aryl and alkyl halides and potassium sulfide has been described. K2S acts as an inexpensive and readily available sulfur source. A variety of symmetric diaryl and dialkyl disulfides was prepared in good to excellent yields using NiCl2·6H2O and acetylacetone as the catalytic system. Graphical abstract: [Figure not available: see fulltext.]
- Soleiman-Beigi, Mohammad,Arzehgar, Zeinab
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p. 1759 - 1763
(2016/09/28)
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- Catalyst-Free, Regioselective Ring Opening of Donor-Acceptor Cyclopropanes: Synthesis of Functionalized Mono- and Disulfides
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Interesting sulfur compounds such as monosulfides, symmetrical disulfides, unsymmetrical disulfides, and other 1,3-bifunctionalized compounds were synthesized using benzyltriethylammonium tetrathiomolybdate, [BnNEt3]2MoS4, as the sulfur transfer reagent via regioselective ring opening of donor-acceptor cyclopropanes without the addition of any catalyst.
- Gopinath, Purushothaman,Chandrasekaran, Srinivasan
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p. 3087 - 3096
(2016/09/09)
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- Microwave-assisted synthesis of 3-sulfenylindoles by sulfonyl hydrazides using organic ionic base-Br?nsted acid
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A novel, efficient, and high-yielding method was developed for the synthesis of 3-sulfenylindoles via a DBU-based ionic liquid promoted sulfenylation of indoles using sulfonyl hydrazides as a thiol surrogate. The environmentally friendly procedure, easy operation and mild reaction conditions enable the tolerance of a wide scope of functionalities as well as high reaction efficiency. The synthetic procedure is suitable for both N-protected or unprotected indoles.
- Rahaman, Rajjakfur,Devi, Namita,Sarma, Kuladip,Barman, Pranjit
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p. 10873 - 10879
(2016/02/05)
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- Tunable and Practical Synthesis of Thiosulfonates and Disulfides from Sulfonyl Chlorides in the Presence of Tetrabutylammonium Iodide
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A tunable and practical synthesis of electrophilic sulfenylating reagents, thiosulfonates and disulfides, from inexpensive and easily available sulfonyl chlorides, has been developed. By appropriate choice of solvents, the reaction of sulfonyl chlorides and tetrabutylammonium iodide gave the target products in good to excellent yields, respectively. These transformations probably proceed through a reducing–coupling pathway. (Figure presented.).
- Zheng, Yong,Qing, Feng-Ling,Huang, Yangen,Xu, Xiu-Hua
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supporting information
p. 3477 - 3481
(2016/11/13)
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- Metal-free catalytic synthesis of diaryl thioethers under mild conditions
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A novel method to synthesize diaryl thioethers from aryl halides and carbon disulfide catalyzed by the 1,8-diazabicyclo[5,4,0]undec-7-enium acetate [DBUH][OAc] ionic liquid (IL) under solvent-free conditions has been developed. This metal-free catalytic system displayed high efficiency for coupling aryl halides with CS2 to deliver thioethers. Compared to the conventional methods, no metal catalyst was needed, instead of which the DBU-based ILs played the catalyst and solvent roles simultaneously. Some reactions were carried out under mild conditions (55 °C, 0.5 h), giving moderate to high yields. Moreover, compared with the rare reports, the reaction of the aryl chlorides and fluorides with CS2 could smoothly react in this catalytic system. The products were easily separated from the ILs which could be reused at least three times. The present method provides an efficient and environment-friendly catalytic approach to synthesize diaryl thioethers.
- Cao, Xian-Ting,Zhang, Peng-Fei,Zheng, Hui
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supporting information
p. 6762 - 6767
(2016/08/10)
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- An efficient one-pot method for the direct synthesis of organic disulfides from aryl/alkyl halides in the presence of CuCl using morpholin-4-ium morpholine-4-carbo-dithioate
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A novel and expedient route is described for the one-pot synthesis of symmetric diaryl (dialkyl) disulfides derivatives via morpholin-4-ium morpholine-4-carbo-dithioate and aryl (alkyl) halides reactions in the presence of CuCl in an aqueous solvent system. Morpholin-4-ium morpholine-4-carbo-dithioate used as new solid, stable and easy handle sulfur Sourcage.
- Soleiman-Beigi, Mohammad,Arzehgar, Zeinab
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p. 395 - 402
(2015/06/22)
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- Mild and selective catalytic oxidation of organic substrates by a carbon nanotube-rhodium nanohybrid
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A heterogeneous catalyst was assembled by stabilization of rhodium nanoparticles on carbon nanotubes. The nanohybrid was used for the catalytic aerobic oxidation of diverse substrates such as hydroquinones, hydroxylamines, silanes, hydrazines and thiols, at room temperature. The system proved very efficient on the investigated substrates and demonstrated high selectivity.
- Donck, Simon,Gravel, Edmond,Li, Alex,Prakash, Praveen,Shah, Nimesh,Leroy, Jocelyne,Li, Haiyan,Namboothiri, Irishi N. N.,Doris, Eric
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p. 4542 - 4546
(2015/09/01)
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- RECOVERY METHOD OF 4,4'-DINITRODIPHENYL SULFIDE
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PROBLEM TO BE SOLVED: To provide a recovery method of 4,4'-dinitrodiphenyl sulfide, which dissolves such the conventional problem that it is difficult to achieve recovery of 4,4'-dinitrodiphenyl sulfide with high purity and at a high recovery rate as well
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-
Paragraph 0045-0051
(2018/12/01)
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- Investigation of solvent-dependent catalytic behaviour of hydrophobic guest artificial glutathione peroxidase using cumene hydroperoxide and 4-nitrobenzenethiol as substrates
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The catalytic behaviour of a hydrophobic guest glutathione peroxidase (ADA-Te-ADA) was detailed investigated using cumene hydroperoxide and 4-nitrobenzenethiol as substrates. The relation between the catalytic rate of artificial glutathione peroxidase and the property of solvent used in the determination of catalytic rate was revealed. Herein, C2H5OH, DMSO, DMF and CH3CN were selected as the co-solvents in the determination of catalytic rates. The typical solvent-dependent catalytic behaviour of ADA-Te-ADA was exhibited. Especially, the higher catalytic rate was observed when polar protic solvent (ethanol) was used compared with other co-solvents. It suggested that polar protic solvent was the appropriate co-solvent for the assay of catalytic activity of hydrophobic artificial glutathione peroxidase. Additionally, the strong polarity of polar aprotic solvent plays an important role in the enhancement of glutathione peroxidase catalytic activity. This study suited well for the understanding of the catalytic behaviour of hydrophobic guest artificial glutathione peroxidase.
- Jiao,Yin,Hu,Shi,Gan,Liang,Huang,Zhang
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p. 1671 - 1674
(2015/03/04)
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- Efficient silver-catalyzed direct sulfenylation and selenylation of rich arenes
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An efficient protocol for silver/copper-cocatalyzed direct sulfenylation and selenylation of arenes with aryl disulfides and diselenides has been developed. This strategy exhibits excellent functional group tolerance and high regioselectivity. Mono sulfenylation and selenylation products can be exclusively achieved. This reaction provides a simple and practical route to the preparation of aryl sulfides and selenides. This journal is
- Yan, Guobing,Borah, Arun Jyoti,Wang, Lianggui
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supporting information
p. 9557 - 9561
(2015/02/19)
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- Synthesis of disulfides and diselenides by copper-catalyzed coupling reactions in water
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A simple and efficient protocol for copper-catalyzed coupling reactions between aryl halides and elemental sulfur or selenium has been developed. A variety of disulfides and diselenides can be obtained in moderate to excellent yields up to 96%. The Royal Society of Chemistry 2013.
- Li, Zhengkai,Ke, Fang,Deng, Hang,Xu, Hualong,Xiang, Haifeng,Zhou, Xiangge
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supporting information
p. 2943 - 2946
(2013/07/25)
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- An efficient, one-pot and CuCl-catalyzed route to the synthesis of symmetric organic disulfides via domino reactions of thioacetamide and aryl (alkyl) halides
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In this article, a simple, general and novel method for the synthesis of diaryl (dialkyl) disulfides from aryl (alkyl) halides is described. This is a convenient approach that involves the use of commercially available and inexpensive thioacetamide as a sulfur transfer reagent in the domino process for the synthesis of symmetric organic disulfides. Copyright
- Soleiman-Beigi, Mohammad,Hemmati, Maryam
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p. 734 - 736
(2013/12/04)
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- Aerobic oxidation of thiols to disulfides under ball-milling in the absence of any catalyst, solvent, or base
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An efficient aerobic chemoselective oxidation of thiols to disulfides has been achieved under ball-milling over neutral aluminium oxide (grinding auxiliary) in the absence of any catalyst, co-oxidant, solvent, or base. A wide variety of functionalized diaryl, diheteroaryl and dialkyl disulfides have been obtained in high yields. The Royal Society of Chemistry 2013.
- Chatterjee, Tanmay,Ranu, Brindaban C.
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p. 10680 - 10686
(2013/09/02)
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