- Visible-light-mediated facile synthesis of disulfides using reusable TiO2/MoS2nanocomposite photocatalyst
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A nontoxic and inexpensive TiO2/MoS2nanocomposite was prepared and employed as an efficient photocatalyst for the synthesis of symmetrical disulfides under visible light irradiation at room temperature. Both aryl and alkyl thiols survived the reaction conditions, affording the corresponding disulfides in good to excellent yields. The photocatalyst could be easily recovered by simple centrifugation and filtration and reused several times without significant loss in its activity.
- Liu, Wenjie,Wang, Cancan,Huang, Yibo,Chen, Qun,Wang, Liang,He, Mingyang
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- Substituent Effect on the Rate Constants for the Reactions between Benzenethiyl Radicals and Stable Free Radicals Estimated by Flash Photolysis
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Absolute rate constants for the reactions between para-substituted benzenethiyl radicals and stable free radicals such as di-tert-butyl nitroxide (DBNO.) and galvinoxyl (G.) were determined by means of xenon- and laser-flash photolysis.The rate constants were in the range of 3.3 108 to 1.6 109 M-1 s-1.For both the stable free radicals, the rate constants were correlated with Hammett substituent constant ?+ yielding positive ρ+ values; ρ+(DBNO.) = +0.75 +/- 0.02 and ρ+(G.) = +0.25 +/- 0.05.The observed ρ+ for G. most likely implies that the reactivities are determined mainly by the thermodynamic stabilities of the substituted benzenethiyl radicals.The ρ+ for DBNO., which is considerably larger than the ρ+ for G., may be explained by the contribution of the polar resonance structures to the transition state.
- Nakamura, Michiaki,Ito, Osami,Matsuda, Minoru
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- Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid
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The copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid is reported. The procedure operates under simple conditions to afford the corresponding aryl cyclopropyl sulfides in moderate to excellent yields. The reaction tolerates substitution in ortho-, meta- and para-substitution as well as electron-donating and electron-withdrawing groups. The S-cyclopropylation of a thiophenol was also accomplished using potassium cyclopropyl trifluoroborate.
- Benoit, Emeline,Fnaiche, Ahmed,Gagnon, Alexandre
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- Caro's acid supported on silica gel. Part 1: Oxidative coupling of thiols to disulfides
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Mild and efficient method for preparation of disulfides from thiols is described using Caro's acid supported on silica gel.
- Movassagh,Lakouraj,Ghodrati
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- Conversion of thiols to disulfides using a hexamethylenetetramine-bromine complex
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Hexamethylenetetramine-bromine complex, a yellow-orange, very stable homogeneous solid, affects a mild and fairly general conversion of thiols to disulfides. Copyright Taylor & Francis Group, LLC.
- Yavari, Issa,Rounaqi, Ali A.,Moradi, Loghman
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- Polymer supported reagents: Oxidative selection between thiols
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A very simple reaction is described for the efficient oxidative selection between thiols by Dowex l-X8, as a quaternary ammonium resin, on which Cl- is replaced by dichromate and bisulfate ions (DDB).
- Shirini,Lakouraj,Mohammadpour-Baltork,Asadi
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- Iron-Catalyzed Cross-Dehydrogenative Coupling of Oxindoles with Thiols/Selenols for Direct C(sp3)?S/Se Bond Formation
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The C?X (S/Se) bonds are common and ubiquitous in natural products and pharmaceuticals. Here, we report an iron-catalyzed cross-dehydrogenative coupling (CDC) reaction for the direct synthesis of C(sp3)?X (S/Se) bonds from oxindoles, phenylacetamides, pyrazolones, phenylacetonitriles and ethyl cyanoacetate with thiols and selenols. All the reactions were performed under simple and mild conditions, and air (molecular oxygen) was employed as an ideal green oxidant, thus promising broad application in chemical industry and modification of bioactive molecules. (Figure presented.).
- Huang, Lu-Shan,Han, Dong-Yang,Xu, Da-Zhen
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- Selective and convenient oxidation of thiols to disulfides using n-butyltriphenylphosphonium dichromate (Bun PPh3) 2Cr2O7 in solution, under solvent-free conditions and microwave irradiation
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A variety of aliphatic, aromatic, and heteroaromatic thiols were rapidly and cleanly converted to their corresponding disulfides in excellent yields using n-butyltriphenylphosphonium dichromate (BTPPDC) in acetonitrile solution under solvent-free conditions and microwave irradiation. Selective oxidation of thiols in the presence of other oxidizable functional groups, such as alcohol and sulfide, is a noteworthy advantage of this method.
- Mohammadpoor-Baltork, Iraj,Memarian, Hamid Reza,Bahrami, Kiumars
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- Thiol-Olefin Cooxidation (TOCO) Reaction. 10. Phenyl Allyl Ether and p-Chlorothiophenol
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The TOCO reaction of a hexane solution of phenyl allyl ether and p-chlorothiophenol was investigated under photochemical and thermal activation conditions and over a temperature range of -23 to +25 deg C.The formation of the desired TOCO product, the thiol-olefin anti-Markovnikov adduct, and p-bis(chlorophenyl) sulfide was found to vary both as a function of temperature and of the activating conditions.The equilibrium constants for the formation of the thiol-olefin complexes were determined in the case of phenyl allyl ether and the analogous 4-phenyl-1-butene as well as 1-octene, norbornene, and 1-phenylbutane in order to elucidate the nature of these associations.
- Chung, Moo-Il,D'Souza, Valerian T.,Szmant, H. Harry
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- A direct preparation of functionalized aryl and heteroaryl disulfides from functionalized zinc organometallics by using sulfur monochloride (S 2Cl2)
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A range of functionalized aryl and heteroaryl disulfides has been prepared from zinc organometallics by using sulfur monochloride (S2Cl 2). The zinc reagents were obtained by transmetalation from magnesium or lithium reagents with ZnBr2.
- Korn, Tobias J.,Knochel, Paul
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- Clean and fast oxidative transformation of thiols to disulfides under solvent-free conditions
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We present here a fast, solvent-free synthesis of symmetrical disulfides using solid supported catalyst (Al2O3/KF). The reaction was performed at room temperature, by gentle heating or under MW irradiation. This efficient and improved method is general for liquid thiols, affording the disulfides in good to excellent yields. The catalytic system can be re-used two times without previous treatment and with comparable activity.
- Lenard?o, Eder J.,Lara, Renata G.,Silva, Márcio S.,Jacob, Raquel G.,Perin, Gelson
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- An efficient and convenient method for the preparation of disulfides from thiols using oxygen as oxidant catalyzed by tert-butyl nitrite
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An efficient and convenient tert-butyl nitrite-catalyzed selective aerobic oxidation of thiols has been developed. Under the optimal reaction conditions, a number of thiol derivatives including aromatic thiols, heteroaromatic thiols and aliphatic thiols can be converted into their corresponding disulfides in good to excellent yields.
- Yi, Shan-Li,Li, Mei-Chao,Hu, Xin-Quan,Mo, Wei-Min,Shen, Zhen-Lu
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- Catalytic oxidation of thiols to disulfides using iodine and CeCl3·7H2O in graphite
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A very simple procedure for the efficient oxidation of thiols to disulfides catalyzed by I2/CeCl3·7H2O in graphite and ethyl acetate as the solvent, in an open system at room temperature is described. The reaction proceeds cleanly under mild conditions and was performed with aromatic, aliphatic, and heterocyclic thiols.
- Silveira, Claudio C.,Mendes, Samuel R.
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- PPS Preparation. A Kinetic Study and the Effect of Water on the Polymerization
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A kinetic study on poly(p-phenylene sulfide) formation from p-dichlorobenzene (1) and sodium sulfide reveals that the initiation reaction is first order with respect to 1 and sodium sulfide, respectively.Reaction on the surface of solid sodium sulfide has proved to be neglible when the reaction is carried out in the presence of the solid.The time course of the concentration of 1 and its dimer can be explained with a simplified eight step kinetic model for the initial stage, in which each of the step is first order with respect of the reactant in concern.Kineticparameters for each of the steps were estimated.Increase in / ratio causes the increase both in polymer yield and in the degree of polymerization.Presence of a small amount of water enhances considerably the rate of polymerization and increases the polymer yield, but the highest degree of polymerization was observed in the presence of water approximately equimolar to 1.
- Ito, Masato M.,Onda, Masahiro,Ona, Seiichi,Inoue, Hakuai
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- Benzoyloxymethyl p-toluenethiosulfonate: A crystalline, stable synthetic equivalent for+CH2S+
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Benzoyloxymethyl p-toluenethiosulfonate has been developed as a reagent for the one-pot preparation of α-sulfide disulfides and the corresponding symmetrical bissulfide disulfides. The reagent is effective for systems bearing terminal aryl groups. CSIRO 2005.
- Kabir, S. M. Humayun,Langler, Richard F.
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- Aerobic oxidation of thioles to disulfides catalyzed by mixed-addenda vanadium (V) substituted heteropolyacids
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The oxidation of thiols to related disulfides using mixed-addenda heteropolyacids as catalyst under mild condition has been studied. This system provides an efficient, convenient, and practical method for the syntheses of symmetrical disulfides. In this w
- Rezvani, M. A.,Harutyunyan, R.,Heravi, Majid M.
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- NO2- activation and reduction to no by a nonheme Fe(NO2)2 complex
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The selective reduction of nitrite (NO2-) to nitric oxide (NO) is a fundamentally important chemical transformation related to environmental remediation of NOx and mammalian blood flow. We report the synthesis and characterization of two nonheme Fe complexes, [Fe(LN 4Im)(MeCN)2](BF4)2 (1MeCN) and [Fe(LN4Im)(NO2) 2] (2), geared toward understanding the NO2- to NO conversion. Complex 2 represents the first structurally characterized FeII complex with two axial NO2- ligands that functions as a nitrite reduction catalyst.
- Sanders, Brian C.,Hassan, Sayed M.,Harrop, Todd C.
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- Oxidative coupling of thiols by pyridinium chlorochromate in solution and solvent free conditions
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Oxidative coupling of aromatic and aliphatic thiols is achieved efficiently by pyridinium chlorochromate in solution and solvent free conditions. Omitting the solvent does not change the reaction time and product yield significantly, while the need of using the solvent is suppressed and workup procedure becomes easier.
- Salehi,Farrokhi,Gholizadeh
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- Laccase-catalyzed in situ generation and regeneration of N-phenyltriazolinedione for the aerobic oxidative homo-coupling of thiols to disulfides
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The first report on aerobic in situ generation and regeneration of N-phenyltriazolinedione, a valuable oxidizing agent, from a catalytic amount of N-phenyl urazole in the presence of a laccase enzyme is presented. The application of a 4-phenyl urazole/Laccase/O2 as a new cooperative catalytic oxidation system is reported for a transition-metal-free and halogen free oxidative homo-coupling reaction of structurally diverse thiols to their corresponding disulfides with good to excellent yields in a phosphate buffer solution under mild reaction conditions.
- Khaledian, Donya,Rostami, Amin,Zarei, Seyed Amir
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- Oxidation of Thiols to Bisulfides by Oxygen in Presence of Cobalt(II) and Manganese(II) Salts of 4-Aminobenzoic Acid Supported on Silica Gel
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A mixture of cobalt(II) and manganese(II) salts of 4-aminobenzoic acid supported on silica gel catalyses the oxidation of thiols to disulfides in the presence of oxygen or air.
- Hashemi, Mohammed M.,Karimi-Jaberi, Zahed
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- An Efficient and Selective Solid State Oxidation of Thiols to Disulfides with Quinolinium Fluorochromate on Silica Gel
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Various kinds of aliphatic (cyclic and acyclic), aromatic, and heterocyclic thiols are converted into the corresponding disulfides by quinolinium fluorochromate (QFC) on silica-gel in excellent yields. Selective oxidation of thiols in the presence of sulfides is also achieved under solid phase conditions.
- Tajbakhsh, Mahmood,Mohammadpoor-Baltork, Iraj,Alimohammadi, Kamal
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- Copper-Catalyzed Three-Component Coupling Reaction of Aryl Iodides, a Disilathiane, and Alkyl Benzoates Leading to a One-Pot Synthesis of Alkyl Aryl Sulfides
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A copper-catalyzed three-component coupling reaction of aryl iodides, hexamethyldisilathiane and alkyl benzoates leading to alkyl aryl sulfides has been demonstrated. A disilathiane acted as both a sulfur source and a promoter of the sulfidation, and the alkyl moiety of the alkyl benzoate was effectively introduced on one side of the sulfide. Moreover, we found that the protocol can be expanded to the preparation of ethyl phenyl selenide with diphenyl diselenide.
- Sakai, Norio,Maeda, Hiromu,Ogiwara, Yohei
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- Microwave thermolysis VII: Oxidative coupling of thiol acetates and esters using 'Clayan' in dry media
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Disulfide bond formation by the oxidative cleavage of thiol acetates and thiol esters using 'Clayan' under microwave irradiation is described. The non-metallic and inexpensive nature of the reagent are the important features of the procedure.
- Meshram,Bandyopadhyay,Reddy,Yadav
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- Supported iron oxide nanoparticles: Recoverable and efficient catalyst for oxidative S-S coupling of thiols to disulfides
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Supported iron oxide nanoparticles are found to be efficient and recoverable catalyst in the selective oxidation of thiols to their corresponding disulfides using hydrogen peroxide as green oxidant at room temperature. The protocol features an easy work-up, simplicity and the utilizing mild reaction conditions, as well as high selectivity toward disulfides, are highly advantageous compared to alternative reported methodologies. The supported iron oxide nanoparticles could be easily recovered and reused several times without any loss of activity. ICP-MS results prove that there is no metal leaching observed, and demonstrating the stability of the catalyst under the reaction conditions.
- Rajabi, Fatemeh,Kakeshpour, Tayeb,Saidi, Mohammad Reza
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- S-Trifluoromethylation of Thiols by Hypervalent Iodine Reagents: A Joint Experimental and Computational Study
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The radical trifluoromethylation of thiophenol in condensed phase applying reagent 1 (3,3-dimethyl-1-(trifluoromethyl)-1λ3,2-benziodoxol) has been examined by both theoretical and experimental methodologies. On the basis of ab initio molecular
- Sala, Oliver,Santschi, Nico,Jungen, Stefan,Lüthi, Hans Peter,Iannuzzi, Marcella,Hauser, Nicole,Togni, Antonio
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- Electrochemical Sulfenylation of 4-Hydroxycoumarins with Aryl Thiols Catalyzed by Potassium Iodide
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A KI-catalyzed indirect electrochemical oxidative method for the synthesis of sulfenylated 4-hydroxycoumarins via cross-coupling of 4-hydroxycoumarins and aryl thiols at a low potential has been reported. The electrocatalytic activity of KI for sulfenylat
- Jin, Jiali,Zhao, Lingmin,Zhang, Chao,Liu, Xin,Yin, Wenxu,Shen, Zhenlu,Li, Meichao
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- Aerobic Cross-Dehydrogenative Coupling Reactions for Selective Mono- And Dithiolation of Phenols
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A highly efficient strategy for the direct thiolation of phenols under transition metal-free and solvent-free conditions has been developed. These reactions are operationally simple with employing air (molecular oxygen) as an ideal oxidant and can selectively provide mono- and dithiolation products in good to excellent yields under basic conditions. The reaction tolerates a broad range of aryl thiols and arenes and is especially applicable for large-scale synthesis.
- Han, Dong-Yang,Liu, Xiao-Peng,Li, Ruo-Pu,Xu, Da-Zhen
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supporting information
p. 10166 - 10176
(2021/07/31)
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- Electrochemical Direct Thiolation of Lactams with Mercaptans: An Efficient Access to N-Acylsulfenamides
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An efficient and eco-friendly electrochemical methodology for the oxidative cross coupling hydrogen evolution (CCHE) reactions of lactams with thiols is presented. Various electron deficient N-acylsulfenamides are smoothly produced in modest to excellent yields without using any external oxidant. Elementary mechanistic insight supports a possible free radical process and hydrogen is the only side product. This approach provides a safe, convenient, and economical preparation of synthetically important N-thiophthalimides on a gram scale.
- Wei, Zhaoxin,Wang, Renjie,Zhang, Yonghong,Wang, Bin,Xia, Yu,Abdukader, Ablimit,Xue, Fei,Jin, Weiwei,Liu, Chenjiang
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supporting information
p. 4728 - 4732
(2021/09/10)
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- Application of Bulky NHC-Rhodium Complexes in Efficient S-Si and S-S Bond Forming Reactions
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The efficient and straightforward syntheses of silylthioethers and disulfides are presented. The synthetic methodologies are based on new rhodium complexes containing bulky N-heterocyclic carbene (NHC) ligands that turned out to be efficient catalysts in thiol and thiol-silane coupling reactions. These green protocols, which use easily accessible reagents, allow obtaining compounds containing S-Si and S-S bonds in solvent-free conditions. Additionally, preliminary tests on coupling of mono- and octahydro-substituted spherosilicates with selected thiols have proved to be very promising and showed that these catalytic systems can be used for the synthesis of a novel class of functionalized silsesquioxane derivatives.
- Bo?t, Ma?gorzata,?ak, Patrycja
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supporting information
p. 17579 - 17585
(2021/11/18)
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- Preparation method of symmetric disulfide bond-containing compound
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The method comprises the following steps: adding a raw material and an oxidant to a reaction bottle containing a solvent; reacting 23W - 85W under the irradiation of 12 - 24h energy-saving lamps; and purifying the reaction product to obtain symmetrical disulfide bond-containing compounds. The raw material is mercaptan or thiophenol. The oxidizing agent is trichlorobromomethane, and the solvent is tetrahydrofuran. The method has the advantages of simple operation, high yield (70 - 90%), wide applicability, cheap and easily available raw materials, and provides a better way for the synthesis and production of symmetrical disulfide bond-containing compounds.
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Paragraph 0020; 0057-0059
(2021/11/21)
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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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- Transition-Metal-Free Synthesis of Aryl Trifluoromethyl Thioethers through Indirect Trifluoromethylthiolation of Sodium Arylsulfinate with TMSCF3
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Herein, we report an indirect trifluoromethylthiolation of sodium arylsulfinates. This transition-metal-free reaction significantly provides an environmentally friendly and practical synthetic method for aryl trifluoromethyl thioethers using commercial Ruppert-Prakash reagent TMSCF3. This approach is also a potential alternative to the current industrial production method owing to facile substrates, excellent functional group compatibility, and operational simplicity.
- Zheng, Changge,Jiang, Chao,Huang, Shuai,Zhao, Kui,Fu, Yingying,Ma, Mingyu,Hong, Jianquan
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supporting information
p. 6982 - 6986
(2021/09/08)
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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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- Synthesis of ortho-phenolic sulfilimines via an intermolecular sulfur atom transfer cascade reaction
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To expand the toolbox for the synthesis of ortho-phenolic sulfilimines, sigmatropic rearrangements were introduced to the field of sulfilimine chemistry. Herein we report a N-H sulfenylation/[2,3]-sigmatropic rearrangement cascade reaction. This mild reaction enables commercially available thiols to serve as the sulfenylation reagent and generates water as the sole byproduct. Moreover, the reaction has a wide substrate scope and can be conducted on a gram scale with excellent reaction efficiency.
- Ren, Yan,Song, Yinan,Xiong, Feng,Xu, Shaojian,Zhang, Linxing,Zhang, Xinhao,Zuo, Yingying
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supporting information
p. 3799 - 3803
(2020/06/08)
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- Electrochemical access to aryl sulfides from aryl thiols and electron-rich arenes with the potassium iodide as a mediator
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An indirect electrooxidation method catalyzed by potassium iodide at a low potential for the synthesis of aryl sulfides from aryl thiols and electron-rich arenes has been developed. Cyclic voltammetry was carried out to investigate the electrocatalytic ac
- Liu, Xin,Niu, Pengfei,Jin, Jiali,Shen, Zhenlu,Li, Meichao
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- Visible-light photocatalytic selective aerobic oxidation of thiols to disulfides on anatase TiO2
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This work presents the visible-light photocatalytic selective oxidation of thiols to disulfides with molecular oxygen (O2) on anatase TiO2. The high specific surface area of anatase TiO2 proved to be especially critical in
- Xu, Hui,Shi, Ji-Long,Lyu, Shaoshuai,Lang, Xianjun
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p. 1468 - 1473
(2020/04/29)
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- TEMPO visible light photocatalysis: The selective aerobic oxidation of thiols to disulfides
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TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl) is well-established in orangocatalysis that usually work in synergy with transition-metal catalysis or semiconductor photocatalysis. Here, TEMPO was turned into a visible light photocatalyst to conduct the selective aerobic oxidation of thiols into disulfides. With O2 as an oxidant, a mild and efficient protocol for the selective oxidation of thiols into disulfides including symmetrical and unsymmetrical ones with 5 molpercent of TEPMO as a photocatalyst was developed at room temperature under the irradiation of 460 nm blue LEDs. It was found that a complex formed between TEMPO and thiols underpinned the visible light activity and disulfides were obtained in very high isolated yields. This work suggests that TEMPO takes diverse roles in for photocatalytic selective oxidative transformations with O2 as the oxidant.
- Xu, Hui,Zhang, Yu-Fei,Lang, Xianjun
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supporting information
p. 1520 - 1524
(2019/12/09)
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- Chemoselective rearrangement reactions of sulfur ylide derived from diazoquinones and allyl/propargyl sulfides
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Here, we describe three types of rearrangement reactions of sulfur ylide derived from diazoquinones and allyl/ propargyl sulfides. With Rh2(esp)2 as the catalyst, diazoquinones react with allyl/propargyl sulfides to form a sulfur ylide, which undergoes a chemoselective tautomerization/[2,3]-sigmatropic rearrangement reaction, a Doyle?Kirmse rearrangement/Cope rearrangement cascade reaction, or a Doyle?Kirmse rearrangement/elimination reaction, depending on the substituent of the sulfides. The protocol provides alkenyl and allenyl sulfides and multisubstituted phenols with moderate and high yields.
- Zhou, Cong-Ying,Yan, Sijia,Rao, Junxin
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supporting information
p. 9091 - 9096
(2020/12/02)
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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 0057-0060
(2020/11/23)
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- Extended Pummerer fragmentation mediated by carbon dioxide and cyanide
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Pummerer rearrangement reactions generate sulfur (II) oxidation state from sulfur (IV) starting materials in the presence of activating reagents. We found unprecedented transformation of vinyl sulfoxide; disulfide formation reactions mediated by atmospheric pressure of carbon dioxide in extended Pummerer rearrangement reactions. Only under CO2 atmosphere, we observed moderate to high yields of disulfide starting from sulfur (IV) starting materials. Investigations on the reaction mechanism revealed that the degradation of the starting materials and the products was significant in the absence of CO2. Further evidence for the suggested reaction mechanism was obtained by a cross-over experiment and a radical trapping reagent.
- Liu, Jian,Kragh, Rasmus R.,Kamounah, Fadhil S.,Lee, Ji-Woong
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supporting information
(2020/10/30)
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- Photoredox β-thiol-α-carbonylation of enones accompanied by unexpected Csp2-C(CO) bond cleavage
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An olefinic difunctionalization method of enones was presented hereviaaerobic visible-light catalysis. A novel reactivity was showcased in conjunction with the selective Csp2-C(CO) bond activation of enones, which provided a convenient method for the preparation of various β-thiolated-α-functionalized compounds. Moreover, the preliminary investigation of the mechanism indicated that a β-peroxysulfide intermediate was formed under the promotion of visible light under an oxygen atmosphere, which finally induced the unexpected C-C bond cleavage.
- Du, Ding,Feng, Jie,Ma, Rui,Zhang, Beichen,Zhang, Kuili
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supporting information
p. 7549 - 7553
(2020/10/13)
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- Diaryl disulfides and thiosulfonates as combretastatin A-4 analogues: Synthesis, cytotoxicity and antitubulin activity
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Diaryl disulfides and diaryl thiosulfonates were synthesized with the two phenyl rings of all compounds bearing identical halide substituents. Because of structural similarity to the potent antimitotic natural product combretastatin A-4 (CA-4), the compounds were examined for inhibition of tubulin polymerization, and the thiosulfonates were more active than the disulfides. The nine thiosulfonates had IC50 values ranging from 1.2 to 9.1 μM, as compared with 1.3 μM obtained with CA-4. The compounds thus ranged from equipotent with CA-4 to 7-fold less active. The nine disulfides had IC50 values ranging from 1.2 to 5.1 μM, as compared with 0.54 μM obtained with CA-4. The compounds thus ranged from less than half as active as CA-4 to over 9-fold less active. The most active members of each group, 2 g and 3c, in the assembly assay were modeled into the colchicine site. Compound 3c had significant hydrophobic interactions with β-tubulin residues CYS 241 and ALA 250, and its thiosulfonate bridge made a hydrogen bond with β-tubulin residue ASN 258. Compound 2 g had hydrophobic interactions with β-tubulin residues ALA 250, CYS 241 and ALA 254, but there was no significant interaction of the disulfide bridge with tubulin.
- Bai, Ruoli,Barbosa, Euzébio Guimar?es,Beatriz, Adilson,Hamel, Ernest,Khodyuk, Rejane Gon?alves Diniz,Louren?o, Estela Mariana Guimar?es,de Lima, Dênis Pires,dos Santos, Edson dos Anjos
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- Synthetic method of diaryl disulfide compound
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The invention relates to a synthetic method of a diaryl disulfide compound. The method comprises the following steps of: in an organic solvent, under the condition of nitrogen, using arylboronic acidand sulfur as the reaction raw materials, carrying out free radical vulcanization/self-polymerization coupling reaction under the action of a transition metal silver catalyst to obtain the diaryl disulfide compound. The method is simple in reaction condition, simple and convenient in experimental operation and high in product yield and purity, opens up a synthetic route and method for preparationof the diaryl disulfide compound, and has good application potential and research value.
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Paragraph 0076-0085
(2020/11/23)
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- Cyclic telluride reagents with remarkable glutathione peroxidase-like activity for purification-free synthesis of highly pure organodisulfides
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Monoamino cyclic tellurides with a five- or six-membered ring structure and their derivatives were developed as a new class of catalyst for the oxidation of organothiols to organodisulfides in a glutathione peroxidase-like catalytic reaction. Quantitative conversion and high reaction rate were achieved by performing the reaction in an organic-aqueous segmented microflow system. Importantly, the process circumvented product purification, which is a major limitation of current organodisulfide synthetic methods.
- Arai, Kenta,Osaka, Yuui,Haneda, Masahiro,Sato, Yuumi
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p. 3647 - 3655
(2019/07/22)
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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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supporting information
p. 1432 - 1438
(2019/03/26)
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- Method for pipeline continuous production of aryl disulfide ether compounds
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The invention discloses a method for pipeline continuous production of aryl disulfide ether compounds, wherein a device comprises a pipe reactor, a raw material storage tank and a gas storage bottle,the method comprises the following steps: adding aryl sulfonyl chloride, a catalyst, water and an alcohol solvent to prepare a material solution, and storing the material solution in the raw materialstorage tank; putting a SO2 gas in the gas storage bottle; when the reaction is started, fully filling the pipe reactor with the alcohol solvent, and then respectively pumping the material solution and the SO2 gas into the pipe reactor for reaction; absorbing a gas discharged by the pipe reactor by an alkali water solution; and removing the solvent from a reaction product discharged from the pipereactor, adding water, filtering, and drying filter cake to obtain the aryl disulfide ether compounds. The method can realize pipeline continuous production of the aryl disulfide ether compounds, thereaction conditions are simple, the post-treatment is convenient, and the yield is high.
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Paragraph 0040-0073
(2019/07/04)
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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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- 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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- The solvent-controlled chemoselective construction of C-S/S-S bonds via the Michael reaction/thiol coupling of quinoline-2-thiones
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K2CO3-catalyzed thio-Michael addition using quinoline-2-thiones and α,β-unsaturated carbonyl compounds was used to assess the chemoselective construction of C-S and S-S bonds under mild reaction conditions in different solvents. The C-S bond showed a better chemoselective construction in EtOH whereas the S-S bond showed a better chemoselective construction in 1,4-dioxane. The corresponding products, generated from the reaction, presented a significant solvent-controlling effect.
- Zhang, Xi,Wang, Tong-Lin,Liu, Xiao-Jun,Wang, Xi-Cun,Quan, Zheng-Jun
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supporting information
p. 2379 - 2383
(2019/03/06)
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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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- Base-controlled Fe(Pc)-catalyzed aerobic oxidation of thiols for the synthesis of S-S and S-P(O) bonds
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Fe(Pc)-Catalyzed aerobic oxidation of thiols for the synthesis of disulfides has been developed under mild reaction conditions. In addition, an aerobic oxidative cross-dehydrogenative coupling (CDC) reaction of thiols with P(O)-H compounds (H-phosphonates and H-phosphine oxide) for the formation of S-P(O) bonds has been demonstrated under the Fe(Pc) catalysis system with a base additive. Control experiments revealed that the use of a base (DIPA) in this system controls the synthetic pathways in which thiophosphates are formed.
- Huang, Hai,Ash, Jeffrey,Kang, Jun Yong
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p. 4236 - 4242
(2018/06/21)
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- Nitrosonium ion catalysis: aerobic, metal-free cross-dehydrogenative carbon-heteroatom bond formation
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Catalytic cross-dehydrogenative coupling of heteroarenes with thiophenols and phenothiazines has been developed under mild and environmentally benign reaction conditions. For the first time, NOx+ was applied for catalytic C-S and C-N bond formation. A comprehensive scope for the C-H/S-H and C-H/N-H cross-dehydrogenative coupling was demonstrated with >60 examples. The sustainable cross-coupling conditions utilize ambient oxygen as the terminal oxidant, while water is the sole by-product.
- Bering, Luis,D'Ottavio, Laura,Sirvinskaite, Giedre,Antonchick, Andrey P.
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supporting information
p. 13022 - 13025
(2018/11/23)
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- Highly efficient, green, rapid, and chemoselective oxidation of sulfur-containing compounds in the presence of an MCM-41@creatinine@M (M = la and Pr) mesostructured catalyst under neat conditions
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In the present study, we report the synthesis of two green recoverable catalysts by covalent linking of the creatinine La and Pr complexes on an MCM-41 mesostructure with the commercially available materials and via a simple and inexpensive procedure. These heterogeneous catalysts were characterized by Fourier transform infrared spectroscopy, energy-dispersive X-ray spectroscopy, scanning electron microscopy, N2 adsorption and desorption, inductively coupled plasma optical emission spectroscopy, and thermogravimetric analysis. The obtained mesostructures act as active and reusable catalysts for the oxidation of sulfides and oxidative coupling of thiols under neat conditions. More importantly, significant practical advantages of this environmentally friendly process include high efficiency, good reaction times, and convenient recovery and reusability for several times without any significant loss of activity of the catalyst.
- Tamoradi, Taiebeh,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
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p. 5479 - 5488
(2018/03/30)
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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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supporting information
p. 1927 - 1938
(2018/07/21)
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- PTAB mediated open air synthesis of sulfonamides, thiosulfonates and symmetrical disulfanes
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A facile methodology has been described which has successfully simplified the generation of sulfonamides, thiosulfonates and symmetric disulfanes. This “trio” of reactions occur in an open air metal free atmosphere and has also been scaled up to grams making it suitable for commercialization. The reactions also have been successfully carried out with asymmetric variants, thus contributing to the chiral pool. The user friendly “trio” enables easy generation of these versatile sulfur analogues and the reaction condition employed depict an economic outline.
- Sarkar, Debayan,Ghosh, Manoj Kumar,Rout, Nilendri
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p. 2360 - 2364
(2018/05/24)
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- Reusable cobalt-phthalocyanine in water: Efficient catalytic aerobic oxidative coupling of thiols to construct S-N/S-S bonds
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A new aerobic oxidative coupling of thiols in water to construct sulfenamides or disulfides was developed, utilizing cobalt(ii)phthalocyanine-tetra-sodium sulfonate as the catalyst and O2 as the oxidant. The mother liquor could be recycled up to 20 times with negligible loss of activity and only a minor decrease of product yield.
- Dou, Yingchao,Huang, Xin,Wang, Hao,Yang, Liting,Li, Heng,Yuan, Bingxin,Yang, Guanyu
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supporting information
p. 2491 - 2495
(2017/07/17)
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- Method for catalyzing molecular oxygen to oxidize into disulfides with S-S bonds in aqueous phase
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The invention provides a method for catalyzing molecular oxygen to oxidize into disulfides with S-S bonds in an aqueous phase. The method includes taking water-soluble transition metal phthalocyanine compounds as catalysts, and enabling sulfhydryl compounds to react for 1-30 hours in the aqueous phase at a pressure of 0.01-1.00 Mpa, at 40-100 DEG C and in the presence of oxygen or air so as to obtain the disulfides with the S-S bonds. The method has the advantages that reaction is conducted in the aqueous phase, so that addition of other organic solvents is unneeded; the catalysts are high in catalytic activity, high in reaction efficiency and reusable; the method is simple in synthetic process, high in product selectivity, fewer in byproducts and wastes and environment friendly, thereby being promising in industrial application prospect.
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Paragraph 0022; 0023; 0029; 0030
(2017/08/29)
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- Oxidative dimerization of thiols to disulfide using recyclable magnetic nanoparticles
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Abstract: Dimerization of thiol groups to disulfide is an important transformation in chemical processes. In this study, magnetic ion exchanged Montmorillonite-k10 was synthesized and characterized using FTIR, X-ray diffraction and scanning electron microscope techniques. Then, the application of the synthesized catalyst as an efficient oxidizing agent was evaluated in oxidative dimerization of different thiols to corresponding disulfides under optimal reaction conditions. The reaction was easily performed with aromatic, aliphatic and heterocyclic thiols. The magnetic catalyst was easily recovered by applying an external magnet and, further, was reused in successive reactions. Graphical Abstract: [Figure not available: see fulltext.]
- Masnabadi, Nasrin,Ghasemi, Mohammad Hadi,Beyki, Mostafa Hossein,Sadeghinia, Mohammad
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p. 1609 - 1618
(2017/02/15)
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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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- Mechanochemically-assisted solid-state photocatalysis (MASSPC)
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In this proof-of-concept study, we demonstrate the first successful transfer of transition metal-free photocatalysis from the conventional solution environment into the solid state, which is enabled by simultaneous irradiation with visible light and mecha
- ?trukil, Vjekoslav,Sajko, Igor
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supporting information
p. 9101 - 9104
(2017/08/18)
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- Dehydrogenative Coupling Reactions with Oxidized Guanidino-Functionalized Aromatic Compounds: Novel Options for σ-Bond Activation
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We present a new option for metal-free σ-bond activation, making use of oxidized, guanidino-functionalized aromatic compounds (GFAs). We demonstrate this new option by the homocoupling reactions of thiols and phosphines. The kinetics and the reaction pathway were studied by a number of experiments (including heterocoupling of thiols and phosphines), supported by quantum-chemical computations. Reaction of the oxidized GFA with p-dihydrobenzoquinone to give p-benzoquinone shows that typical proton-coupled electron-transfer reactions are also possible.
- Wild, Ute,Federle, Stefanie,Wagner, Arne,Kaifer, Elisabeth,Himmel, Hans-J?rg
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supporting information
p. 11971 - 11976
(2016/08/16)
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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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- 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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- 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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p. 90046 - 90050
(2016/10/07)
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- Metal-Free Photocatalytic Aerobic Oxidation of Thiols to Disulfides in Batch and Continuous-Flow
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Disulfides represent significant molecular and structural features in various biologically active compounds and fine chemicals. Therefore, the development of mild, efficient and sustainable methods to access disulfides is of great importance. Here, we describe the development of a mild metal-free photocatalytic aerobic oxidation of thiols to disulfides using Eosin Y and visible-light irradiation. A continuous flow procedure was developed to accelerate the photocatalytic process, enabling the preparation of disulfides with high purity in a timeframe of minutes. The mildness and applicability of our method was exemplified by the flow synthesis of the cyclic peptide hormone, oxytocin, requiring only a 200s reaction time and an efficient one-pot batch protocol for the preparation of the therapeutic thiuram disulfide, disulfiram.
- Talla, Ali,Driessen, Brian,Straathof, Natan J. W.,Milroy, Lech-Gustav,Brunsveld, Luc,Hessel, Volker,No?l, Timothy
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supporting information
p. 2180 - 2186
(2015/07/27)
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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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supporting information
p. 5578 - 5582
(2015/09/21)
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- Carbon monoxide release properties and molecular structures of phenylthiolatomanganese(i) carbonyl complexes of the type [(OC)4Mn(μ-S-aryl)]2
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Several phenylthiolatomanganese carbonyl complexes of the type [(OC)4Mn(μ-SR)]2 (R = Ph (1a), C6H4-4-CH3 (1b), C6H4-4-CF3 (1c), C6H4-4-F (1d), C6H4-4-Cl (1e), C6H4-4-OMe (1f), C6F5 (1g), and CH2C6H4-4-Cl (1h)) have been prepared via the reaction of Mn2(CO)10 with diaryldisulfane or via the reaction of [(OC)5MnBr] with arylthiols. These complexes lose two carbon monoxide molecules quite easily yielding tetranuclear [(OC)3Mn(μ3-SR)]4 (2). Derivatives with fluoro-substituted aryl groups commonly form mixtures of dinuclear 1 and tetranuclear 2 which can quantitatively be converted to 2 by heating of the corresponding reaction mixtures. A unique trinuclear structure is found for the mesityl derivative [(OC)4Mn(μ-SMes)]3 (3) which is maintained in solution as verified by IR and NMR spectroscopy. Traces of an already known dinuclear by-product of the type [(OC)3Mn(μ-SC6H3(-4-Me)-2-SC6H4-4-Me)]2 (4) have been structurally characterized. The suitability of [(OC)4Mn(μ-SPh)]2 (1a) as a CO releasing molecule (CORM) for the administration of carbon monoxide has been studied. Two CO molecules are released upon dissolving in strongly Lewis basic solvents L, yielding [(OC)3Mn(L)(μ-SPh)]2, which liberates all the remaining CO molecules upon irradiation (photoCORM behavior). This journal is
- Mede, Ralf,Lorett-Velsquez, Vaneza Paola,Klein, Moritz,G?rls, Helmar,Schmitt, Michael,Gessner, Guido,Heinemann, Stefan H.,Popp, Jürgen,Westerhausen, Matthias
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p. 3020 - 3033
(2015/03/05)
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- Deep eutectic mixture catalysed the synthesis of disulfides using Bunte salts as thiol surrogates
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Bunte salts, easily prepared from odourless sodium thiosulfates and various alkyl and aryl halides, acted as thiol surrogates for preparation of disulfides in the presence of hydrogen peroxide and a Bronsted-acidic deep eutectic mixture. The reaction proceeded smoothly to give the corresponding disulfide products in moderate to good yields, leaving odourless sodium bisulfite and water as the by-products. Moreover, this catalytic system could be readily recovered and reused several times without significant loss in activity.
- Zhou, Yongsheng
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p. 332 - 335
(2015/08/18)
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