- Highly efficient rhenium-catalyzed deoxygenation of sulfoxides without adding any reducing agent
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This work reports a novel method for the deoxygenation of aromatic and aliphatic sulfoxides catalyzed by oxo-rhenium complexes without adding any reducing agent. The oxo-rhenium complex ReOCl3(PPh3) 2 proved to be very efficient for the deoxygenation of several sulfoxides with tolerance of different functional groups.
- Sousa, Sara C.A.,Bernardo, Joana R.,Rom?o, Carlos C.,Fernandes, Ana C.
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- Palladium on charcoal as a recyclable catalyst for C - S cross-coupling of thiols with aryl halides under ligand-free conditions
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5-Arylation of a wide variety of substituted aryl and aliphatic thiols with aryl halides using a catalytic amount of palladium on charcoal as a heterogeneous catalysis with potassium hydroxide as the base in dimethyl sulfoxide (DMSO) at 110°C is accomplished in good yields. The C. - S bond formation reaction functions under ligand-free conditions, and the palladium on charcoal catalyst can be is reused for five runs without any loss of activity.
- Jiang, Zheng,She, Jin,Lin, Xufeng
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- An efficient protocol for the synthesis of thioethers via iron-catalyzed cross-coupling reaction and its mechanistic investigation
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One of the most straightforward methods for the synthesis of diaryl sulfides is the transition metal catalyzed C–S coupling reaction. Herein we report a study on the iron-catalyzed protocol for cross-coupling reaction of aryl halides with thiols. Structurally diverse diaryl sulfides were prepared efficiently by using a catalyst system involving cheap and environment-friendly FeCl3 and non-toxic universal ligand L-proline. The reaction mechanism for the iron-catalyzed C–S coupling reaction was investigated by means of density functional theory (DFT) methods on a model system. The calculations were performed using hybrid PBE1PBE functional in conjugation with the LANL-2DZ basis set. The key step involved in the mechanism is the formation of a reactant complex in which both reactants are electrostatically bound to Fe(III) proline complex catalyst. The elimination of HI occurs with a much lower TS energy (20.0 kcal/mol) than the uncatalyzed reaction (44.7 kcal/mol).
- Sindhu,Abi,Mathai, George,Anilkumar, Gopinathan
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- Cu2O/SiC as efficient catalyst for Ullmann coupling of phenols with aryl halides
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A Cu2O/SiC heterogeneous catalyst was prepared via a two-step liquid-phase method using diethylene glycol as both the solvent and the reducing agent. The catalyst was characterized using X-ray diffraction, X-ray photoelectron spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), and H2 temperature-programmed reduction. All the results indicate that Cu is present on the SiC support primarily as Cu2O. The SEM and TEM results show that cubic Cu2O nanoparticles are uniformly dispersed on the β-SiC surface. The reaction conditions, namely the temperature, reaction time, and amounts of base and catalyst used, for the Ullmann-type C–O cross-coupling reaction were optimized. A model reaction was performed using iodobenzene (14.0 mmol) and phenol (14.0 mmol) with Cu2O/SiC (5 wt% Cu) as the catalyst, Cs2CO3 (1.0 equiv.) as the base, and tetrahydrofuran as the solvent at 150 °C for 3 h; a yield of 97% was obtained and the turnover frequency (TOF) was 1136 h?1. The Cu2O/SiC catalyst has a broad substrate scope and can be used in Ullmann-type C–O cross-coupling reactions of aryl halides and phenols bearing a variety of different substituents. The catalyst also showed high activity in the Ullmann-type C–S cross-coupling of thiophenol with iodobenzene and substituted iodobenzenes; a TOF of 1186 h?1 was achieved. The recyclability of the Cu2O/SiC catalyst in the O-arylation of phenol with iodobenzene was investigated under the optimum conditions. The yield decreased from 97% to 64% after five cycles. The main reason for the decrease in the catalyst activity is loss of the active component, i.e., Cu2O.
- Wang, Yibing,Guo, Xiaoning,Lü, Manqian,Zhai, Zhaoyang,Wang, Yingyong,Guo, Xiangyun
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- A Highly Efficient Copper-Catalyzed Synthesis of Unsymmetrical Diaryl- and Aryl Alkyl Chalcogenides from Aryl Iodides and Diorganyl Disulfides and Diselenides
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An efficient and convenient protocol has been developed for the copper-catalyzed reaction of aryl iodides and diorganyl disulfides and diselenides. A variety of symmetrical and unsymmetrical diaryl- and aryl alkyl chalcogenides were synthesized with good functional group tolerance and chemoselectivity by using copper(I) iodide as a catalyst, 4′-(4-methoxyphenyl)-2,2′:6′,2′′-terpyridine as ligand, and KOH as base under an inert atmosphere.
- Movassagh, Barahman,Hosseinzadeh, Zhila
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- The first N-heterocyclic carbene-based nickel catalyst for C-S coupling
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We have developed the first N-heterocyclic carbene (NHC)-based transition metal catalysts for C-S coupling reactions. Ni-NHC catalysts showed good to excellent activities toward various aryl halides in C-S coupling reactions. The catalytic activities were greatly affected by the electronic and steric properties of the NHC ligands. The new catalysts were inexpensive, easy to synthesize, and environmentally friendly. They could be excellent candidates to replace Pd-organophosphanes for C-S coupling catalysis.
- Yugen, Zhang,Kao, Chin Ngeow,Ying, Jackie Y.
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- Simple, efficient and recyclable catalytic system for performing copper-catalyzed C-S coupling of thiols with aryl iodides in PEG and PEG-H2O
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A new protocol for the coupling of aryl iodides with thiophenols or alkanethiols is reported. The reaction is catalyzed by CuI-PEG or CuI-PEG-H2O system in the absence of ligands and volatile organic solvents. A variety of functionalized aryl sulfides are prepared in excellent yields. The isolation of the products is readily performed by the extraction with diethyl ether or petroleum ether, and the CuI-PEG catalyst can be reused without significant loss in activity. The simple catalytic system is economically competitive and environmentally friendly.
- She, Jin,Jiang, Zheng,Wang, Yanguang
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- Magnetic nanoparticle-supported Pd(II)-cryptand 22 complex: An efficient and reusable heterogeneous precatalyst in the Suzuki-Miyaura coupling and the formation of aryl-sulfur bonds in honor and memory of late Prof. Mathias Mertes
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In the present work, silica-coated magnetic nanoparticles [Fe3O4@SiO2@C22-Pd(II)] were prepared and characterized by transmission electron microscopy, Fourier transform infrared spectroscopy, vibrating sample magnetometer, energy dispersive X-ray analysis, X-ray photoelectron spectroscopy, elemental analysis, inductively coupled plasma, thermogravimetric and differential thermal analysis. This heterogeneous catalyst is utilized as an effective catalyst for the Suzuki-Miyaura coupling of arylboronic acids and aryl halides, and the cross-coupling reaction of aryl halides and thiols. The catalyst was easily separated by magnetic decantation and the recovered catalyst was reused for five cycles without any significant loss of the catalytic activity.
- Movassagh, Barahman,Takallou, Ahmad,Mobaraki, Akbar
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- Polystyrene resin-supported CuI-cryptand 22 complex: a highly efficient and reusable catalyst for the formation of aryl–sulfur bonds in aqueous media
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The air and moisture stable polystyrene resin-supported copper(I) iodide-cryptand-22 complex (PS-C22-CuI) behaves as an efficient and robust heterogeneous catalyst in the cross-coupling reaction of aryl halides and thiols in aqueous media. Moreover, the heterogeneous catalyst can be easily recovered by filtration and reused for five cycles without significant loss in activity.
- Rezaei, Nasrin,Movassagh, Barahman
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- Palladium-catalyzed C-S bond formation by using N-amido imidazolium salts as ligands
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N-Amido imidazolium salt was employed as a ligand in the palladium-catalyzed cross-coupling reaction of aryl halides and thiols, and showed good activity in the formation of thioether. The best combination for the coupling with aryl bromides was N-amido imidazolium salt 2 and NaHMDS, and that for the coupling with aryl iodides was N-amido imidazolium salt 1 and KO tBu. The coupling reactions were conducted in the presence of Pd(OAc)2 (1 mol %) in DMSO at 80 C for 12 h.
- Byeun, Aleum,Baek, Kyungkyu,Han, Min Su,Lee, Sunwoo
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- Copper Nanoparticles Stabilized in a Porous Chitosan Aerogel as a Heterogeneous Catalyst for C-S Cross-coupling
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Cu nanoparticles (NPs) embedded into chitosan fibrils act as a heterogeneous catalyst for the C-S coupling of aryl halides and thiophenol in toluene. The catalyst can be reused under optimal conditions with some activity decrease from the first to the second use. Characterization of the reused catalyst shows that Cu NPs do not undergo agglomeration. Cu-chitosan is more active for aryl iodides than aryl bromides and chlorides. The presence of chitosan in a large excess is detrimental for the catalytic activity, probably because of the increase of solvent viscosity. It was found that halides formed as byproducts in the reaction act as a catalyst poison and may influence the extent of Cu leaching.
- Frindy, Sana,El Kadib, Abdelkrim,Lahcini, Mohamed,Primo, Ana,García, Hermenegildo
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- Ligand-free C-S bond formation catalyzed by copper(I) oxide
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An efficient ligand-free Cu2O-catalyzed C-S bond-formation reaction was developed. A large number of diaryl sulfides and alkylaryl sulfides could be rapidly assembled using this new reaction protocol. Georg Thieme Verlag Stuttgart.
- Xu, Hua-Jian,Zhao, Xiao-Yang,Fu, Yao,Feng, Yi-Si
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- Ligand-free copper-catalyzed C-S coupling of aryl iodides and thiols
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(Chemical Equation Presented) A protocol for the copper-catalyzed aryl-sulfur bond formation between aryl iodides and thiophenols is reported. The reaction is catalyzed by a low amount (1-2.5 mol %) of readily available and ligand-free copper iodide salt. A variety of diaryl thioethers are synthesized under relatively mild reaction conditions with good chemoselectivity and functional group tolerance.
- Sperotto, Elena,Van Klink, Gerard P. M.,De Vries, Johannes G.,Van Koten, Gerard
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- A semiconducting supramolecular Co(ii)-metallohydrogel: an efficient catalyst for single-pot aryl-S bond formation at room temperature
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A novel mechanically stable supramolecular Co(ii)-metallohydrogel has been synthesized. Cobalt(ii) nitrate hexahydrate and monoethanolamine, as a low molecular weight organic gelator, are used to get the gel. The mechanical stability of the supramolecular hydrogel was analyzed. The morphology of the supramolecular metallohydrogel was scrutinized. The semiconducting features of the metallohydrogel were studied. The conducting properties of the Co(ii)-metallohydrogel establish a Schottky barrier diode type nature. The catalytic nature of the Co(ii)-metallohydrogel based room temperature single pot aryl-S coupling reaction was explored. Most interestingly, the Co(ii)-metallohydrogel based catalytic aryl-S coupling reaction does not require any column-chromatographic purification protocol to get pure aryl-thioethers. Thus, through this work a semiconducting Schottky barrier diode application and catalytic role in the room temperature single pot aryl-S coupling reaction of a supramolecular Co(ii)-metallohydrogel have been explored.
- Dhibar, Subhendu,Dey, Amiya,Jana, Rajkumar,Chatterjee, Arpita,Das, Gourab Kanti,Ray, Partha Pratim,Dey, Biswajit
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- The copper-nicotinamide complex: Sustainable applications in coupling and cycloaddition reactions
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The crystalline copper(ii)-nicotinamide complex, synthesized via simple mixing of copper chloride and nicotinamide solution at room temperature, catalyzes the C-S, C-N bond forming and cycloaddition reactions under a variety of sustainable reaction conditions.
- Baig, R.B. Nasir,Vaddula, Buchi Reddy,Nadagouda, Mallikarjuna N.,Varma, Rajender S.
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- 1,1,1-Tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols
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1,1,1-Tris(hydroxymethyl)ethane was presented as a new, efficient, and versatile tridentate O-donor ligand suitable for the copper-catalyzed formation of C-N, C-S, and C-O bonds. This inexpensive and commercially available tripod ligand has been demonstrated to facilitate the copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols to afford the corresponding desired products in good to excellent yields.
- Chen, Yao-Jung,Chen, Hsin-Hung
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- Efficient ligand-free copper-catalyzed C-S cross-coupling of thiols with aryl iodides using KF/Al2O3 as base
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We report a mild, convenient, environmentally friendly, and ligand-free synthetic protocol for the cross-coupling reaction of aryl iodides and thiols using 10 mol % CuI with KF/Al2O3 as the base, in DMF at 110 °C. Using this protocol, we have shown that a variety of aryl sulfides can be synthesized in excellent yields from readily available iodides and thiols.
- Feng, Yi-Si,Li, Yuan-Yuan,Tang, Lin,Wu, Wei,Xu, Hua-Jian
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- Efficient C-S cross coupling catalyzed by Cu2O
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A protocol for the copper-catalyzed C-S bond formation between aryl, alkyl, or heteroaryl thiols and aryl or heteroaryl halides is reported. The reaction is catalyzed by Cu2O which shows the highest catalytic activity with ethyl 2-oxocyclohexanecarboxylate ligand in DMSO at 80 °C. The corresponding coupling products are obtained with good to excellent yields under relatively mild reaction conditions with good chemoselectivity and functional group tolerance.
- Xu, Hua-Jian,Zhao, Xiao-Yang,Deng, Jin,Fu, Yao,Feng, Yi-Si
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- Nickel(O)-catalyzed Synthesis of Diaryl Sulfides from Aryl Halides and Aromatic Thiols
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Facile and selective syntheses of various diaryl sulfides from aryl halides and aromatic thiols by the aid of an in situ generated nickel(O) catalyst are reported.The nickel(O) induces a C-S cleavege, as well.
- Takagi, Kentaro
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- Strongly Reducing, Visible-Light Organic Photoredox Catalysts as Sustainable Alternatives to Precious Metals
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Photoredox catalysis is a versatile approach for the construction of challenging covalent bonds under mild reaction conditions, commonly using photoredox catalysts (PCs) derived from precious metals. As such, there is need to develop organic analogues as sustainable replacements. Although several organic PCs have been introduced, there remains a lack of strongly reducing, visible-light organic PCs. Herein, we establish the critical photophysical and electrochemical characteristics of both a dihydrophenazine and a phenoxazine system that enables their success as strongly reducing, visible-light PCs for trifluoromethylation reactions and dual photoredox/nickel-catalyzed C?N and C?S cross-coupling reactions, both of which have been historically exclusive to precious metal PCs.
- Du, Ya,Pearson, Ryan M.,Lim, Chern-Hooi,Sartor, Steven M.,Ryan, Matthew D.,Yang, Haishen,Damrauer, Niels H.,Miyake, Garret M.
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- Anionic Bismuth(III) chloride cluster with diselenide countercations: Application in C-S cross coupling reactions
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The first weakly coordinating anion (WCA) with reactive p-block cation (rPBC) type of [(Bi4Cl16)4-{(LSeSeL)2+}2], L = 1,3-bis(2-benzhydryl-4,6-dimethylphenyl)-1H-imidazole-2(3H), ion pair is reported. The tetranuclear anionic bismuth(III) cluster shows a new type of ladder structure with two different types of Bi(III) coordination modes. In the solid state structure, the tetranuclear bismuth(III) cluster is sandwiched by two diselenide cations through hydrogen bonding interactions. Besides, this ion pair has been efficaciously employed as catalyst in C-S cross-coupling reactions under optimized reaction condition. This ion pair depicted a wide range of substrate scope with different thiols and aryl halides.
- Ganesan, Prabusankar,Mannem, Adinarayana,Muthukumaran, Nirmala
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- An efficient copper-catalyzed carbon-sulfur bond formation protocol in water
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An efficient protocol of copper-catalyzed C-S bond formation between aryl halides and potassium thiocyanate leading to diaryl sulfides is reported. A variety of diaryl sulfides can be synthesized in good to excellent yields up to 94%.
- Ke, Fang,Qu, Yanyang,Jiang, Zhaoqiong,Li, Zhengkai,Wu, Di,Zhou, Xiangge
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- Recyclable NHC-Ni complex immobilized on magnetite/silica nanoparticles for C-S cross-coupling of aryl halides with thiols
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A new type of magnetite/silica nanoparticle-supported N-heterocyclic carbene nickel catalyst (Mag-NHC-Ni) was developed from imidazolium with N-picolyl moieties and used as an efficient catalyst in the C-S coupling of various aryl halides with thiols. Moreover, the catalyst was easily recovered from the reaction mixture by simple filtration and recycled with almost consistent activity. Georg Thieme Verlag Stuttgart · New York.
- Yoon, Hyo-Jin,Choi, Jung-Woo,Kang, Homan,Kang, Taegyu,Lee, Sang-Myung,Jun, Bong-Hyun,Lee, Yoon-Sik
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- An efficient tris-(2-aminoethyl)amine-CuI-catalyzed thioetherification of thiols with aryl halides
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A robust method has been developed to couple a wide variety of thiols and aryl halides. The C-S bond forming reaction makes use of catalytic copper(I) iodide and the ligand tris-(2-aminoethyl)amine. These conditions tolerate a wide degree of functionality on both aryl halide and thiol reactants and have resulted in numerous examples being synthesized. Commercial availability of the ready to use, inexpensive ligand, tris-(2-aminoethyl)amine and air-stable CuI make the method well suited to generate a diverse array of diaryl thioethers.
- Jogdand, Nivrutti R.,Shingate, Bapurao B.,Shingare, Murlidhar S.
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- Highly active mesoionic chalcogenone zinc(II) derivatives for C-S cross-coupling reactions
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The first mesoionic heavier chalcogenones, L1-L3 [L1 = 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-selone; L2 = 1-(2-mesitylene)-3-methyl-4-phenyltriazolin-5-thione; L3 = 1-(benzyl)-2-3(methyl)-4-phenyltriazolin-5-selone], were isolated and characterised. Density functional theory was used to obtain insights into the σ donor and π accepting nature of mesoionic chalcogenones. Using these new ligands, a series of the first zinc(ii) mesoionic chalcogenone complexes were isolated. Three mono nuclear zinc(ii) chalcogenone complexes, [(L1)Zn(Cl)2(HOMe)] (1), [(L2)Zn(Cl)2(HOMe)] (3) and [(L2)Zn(Br)2(HOMe)] (4), and two dinuclear zinc complexes, [(L1)Zn(Br)(μ2-Br)]2 (2) and [(L3)Zn(Br)(μ2-Br)]2 (5), containing mesoionic thione and selone ligands were synthesized and characterised. These new complexes 1-5 represent the first structurally characterized mesoionic chalcogenone supported metal derivatives. Furthermore, all zinc complexes were characterized by thermogravimetric analysis and UV-vis spectroscopy. The solid-state structures of all zinc complexes were determined by single-crystal X-ray diffraction. The catalytic activities of the zinc(ii) complexes in thioetherification reactions were investigated without scrubbing of oxygen. The scope of the catalytic reactions was explored with a wide range of thiophenols and aryl halides. The diaryl thioethers were obtained in very good yield under mild conditions. The present protocol furnishes a synthetic route for the C-S cross-coupling of thiophenols and aryl halides without scrubbing oxygen and moisture.
- Vaddamanu, Moulali,Prabusankar, Ganesan,Velappan, Kavitha
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- Homoleptic and heteroleptic Zn(ii) selone catalysts for thioetherification of aryl halides without scrubbing oxygen
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Five new mononuclear tetra-coordinated zinc(ii) selones, [Zn(L1)2Cl2] (1), [Zn(L1)2Br2] (2), [{Zn(L2)4}{BF4}2] (3), [{Zn(L2)4}{ClO4}2] (4), and [Zn(L2)2Br2] (5), have been isolated from a one-pot reaction between the corresponding zinc(ii) salt and selone ligand, 1-methyl 3-naphthylmethylimidazoline-2-selone (L1) or 1-isopropyl 3-methylimidazoline-2-selone (L2). All these complexes were characterized by CHN analysis, FT-IR, NMR studies, and single-crystal X-ray crystallography techniques. The Zn(ii) center in 1-5 exhibits a distorted tetrahedral geometry. Besides, 1-5 were employed as catalysts in the thioetherification of aryl halides. The first zinc(ii) catalyst-mediated thioetherification of aryl halides without scrubbing oxygen was demonstrated. Catalysts 1-5 are highly active towards the cross-coupling reaction between aryl halides and thiophenols. The catalytic ability of 1-5 was explored in THF, toluene, and CH3CN solvents with different bases such as K2CO3, Cs2CO3, and NaOtBu. Interestingly, the zinc(ii) center attached to two selone ligands is much more catalytically active than that attached to four selone ligands.
- Vaddamanu, Moulali,Velappan, Kavitha,Prabusankar, Ganesan
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- A general palladium-catalyzed coupling of aryl bromides/triflates and thiols
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(Chemical equation presented) We have developed an efficient palladium-catalyzed carbon-sulfur bond formation reaction of aryl bromides, triflates, and activated aryl chloride. Using this protocol, we have shown tolerance to a wide variety of aryl thiols and alkyl thiols that can also be used as sulfide equivalents.
- Itoh, Takahiro,Mase, Toshiaki
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- Tridentate hydroxy-functionalised MCM-41-immobilised copper(I) complex as an efficient and recyclable catalyst for coupling of aryl iodides with thiols
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The C-S coupling reaction of aryl iodides with thiols was achieved at 110 °C in DMF/dioxane (V/V, 1:9) in the presence of a tridentate hydroxy-functionalised MCM-41-immobilised copper(I) complex [MCM-41-3OH-CuI] with Cs2CO3 as base to afford a variety of diaryl sulfides in good to excellent yields. The MCM-41-3OH-CuI catalyst can be easily recovered by a simple filtration and reused for at least six times without significant loss of activity.
- Yao, Fang,Zhang, Rongli,Wu, Yichao,Cai, Mingzhong
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- Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters
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Decarbonylative synthesis of thioethers from thioesters proceeds in the presence of a catalytic amount of [Rh(cod)Cl]2 (2 mol %). The protocol represents the first Rh-catalyzed decarbonylative thioetherification of thioesters to yield valuable thioethers. Notable features include the absence of phosphine ligands, inorganic bases, and other additives and excellent group tolerance to aryl chlorides and bromides that are problematic using other metals to promote decarbonylation. Gram scale synthesis, late-stage pharmaceutical derivatization, and orthogonal site-selective cross-couplings by C-S/C-Br cleavage are reported.
- Cao, Han,Liu, Xuejing,Bie, Fusheng,Shi, Yijun,Han, Ying,Yan, Peng,Szostak, Michal,Liu, Chengwei
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p. 10829 - 10837
(2021/07/28)
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- Aryl thioether compound and preparation method thereof
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The invention discloses an aryl thioether compound and a synthesis method thereof, wherein an aryl carboxylic acid and a mercaptan (phenol) are used as main raw materials, and a nickel catalyst is prepared. Under the action of the phosphine ligand and the additive, the aryl carboxylic acid and the thiol (phenol) react in an organic solvent, and after the reaction is finished, the corresponding aryl thioether is obtained. The method has the advantages of low cost, high yield, simple and convenient operation, no pollution and the like, and has potential industrial application prospects. The method provides a cheap and green way for preparation of aryl thioether compounds.
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Paragraph 0019
(2021/11/27)
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- Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters
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We report the palladium-catalyzed double-decarbonylative synthesis of aryl thioethers by an aryl exchange reaction between amides and thioesters. In this method, amides serve as aryl donors and thioesters are sulfide donors, enabling the synthesis of valuable aryl sulfides. The use of Pd/Xantphos without any additives has been identified as the catalytic system promoting the aryl exchange by C(O)-N/C(O)-S cleavages. The method is amenable to a wide variety of amides and sulfides.
- Bie, Fusheng,Cao, Han,Liu, Chengwei,Liu, Xuejing,Shi, Yijun,Szostak, Michal,Zhou, Tongliang
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p. 8098 - 8103
(2021/10/25)
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- Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds
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A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.
- Lam, Long Yin,Ma, Cong
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supporting information
p. 6164 - 6168
(2021/08/16)
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- Bimetallic BaMoO4 nanoparticles for the C-S cross-coupling of thiols with haloarenes
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We disclosed new bimetallic BaMoO4 nanoparticles for the C-S cross-coupling reaction. The C-S cross-coupling reaction of alkyl/aryl thiols with haloarenes was accomplished with high yields. The reaction has good functional group tolerance and selectivity. This is an efficient protocol for synthesizing the building blocks of pharmaceuticals containing C-S bonds. The catalyst is recyclable. The unactivated bromo- and 4-acetyl fluoro-arenes can well couple to afford thioethers in high yields. The reaction is believed to proceed by oxidative addition and reductive elimination.
- Panda, Subhalaxmi,Sahu, Santosh Kumar,Behera, Pradyota Kumar,Panigrahi, Reba,Garnaik, Bamakanta,Rout, Laxmidhar
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supporting information
p. 2500 - 2504
(2020/02/20)
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- CuMoO4 Bimetallic Nanoparticles, An Efficient Catalyst for Room Temperature C?S Cross-Coupling of Thiols and Haloarenes
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CuII catalyst is less efficient at room temperature for C?S cross-coupling. C?S cross-coupling by CuII catalyst at room temperature is not reported; however, doping of copper with molybdenum metal has been realized here to be more efficient for C?S cross-coupling in comparison to general CuII catalyst. The doped catalyst CuMoO4 nanoparticle is found to be more efficient than copper. The catalyst works under mild conditions without any ligand at room temperature and is recyclable and effective for a wide range of thiols and haloarenes (ArI, ArBr, ArF) from milligram to gram scale. The copper-based bimetallic catalyst is developed and recognized for C?S cross-coupling of haloarenes with alkyl and aryl thiols.
- Panigrahi, Reba,Sahu, Santosh Kumar,Behera, Pradyota Kumar,Panda, Subhalaxmi,Rout, Laxmidhar
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p. 620 - 624
(2019/12/27)
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- Exploration of the mechanism and scope of the CuI/DABCO catalysed C–S coupling reaction
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A cost effective and easily available CuI/DABCO catalytic system has been developed for the C–S cross-coupling reaction. This method is extremely useful for the thioetherification of aryl and heteroaryl halides, providing excellent yields and good chemoselectivity. We have also explored the mechanism of the reaction using DFT studies.
- Thomas, Anns Maria,Sherin,Asha, Sujatha,Manojkumar,Anilkumar, Gopinathan
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supporting information
(2019/12/26)
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- Achieving Nickel Catalyzed C-S Cross-Coupling under Mild Conditions Using Metal-Ligand Cooperativity
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A simple and efficient approach of C-S cross-coupling of a wide variety of (hetero)aryl thiols and (hetero)aryl halides under mild conditions, mostly at room temperature, catalyzed by well-defined singlet diradical Ni(II) catalysts bearing redox noninnocent ligands is reported. Taking advantage of ligand centered redox events, the high-energetic Ni(0)/Ni(II) or Ni(I)/Ni(III) redox steps were avoided in the catalytic cycle. The cooperative participation of both nickel and the coordinated ligands during oxidative addition/reductive elimination steps allowed us to perform the catalytic reactions under mild conditions.
- Sikari, Rina,Sinha, Suman,Das, Siuli,Saha, Anannya,Chakraborty, Gargi,Mondal, Rakesh,Paul, Nanda D.
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p. 4072 - 4085
(2019/04/01)
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- Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts
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A general, highly selective method for decarbonylative thioetherification of aryl thioesters by C-S cleavage is reported. These reactions are promoted by a commercially-available, user-friendly, inexpensive, air- and moisture-stable nickel precatalyst. The process occurs with broad functional group tolerance, including free anilines, cyanides, ketones, halides and aryl esters, to efficiently generate thioethers using ubiquitous carboxylic acids as ultimate cross-coupling precursors (cf. conventional aryl halides or pseudohalides). Selectivity studies and site-selective orthogonal cross-coupling/thioetherification are described. This thioester activation/coupling has been highlighted in the expedient synthesis of biorelevant drug analogue. In light of the synthetic utility of thioethers and Ni(ii) precatalysts, we anticipate that this user-friendly method will be of broad interest.
- Liu, Chengwei,Szostak, Michal
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supporting information
p. 2130 - 2133
(2018/03/06)
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- PHOTOCATALYST-FREE, LIGHT-INDUCED CARBON-SULFUR CROSS-COUPLING METHODS
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In one aspect, the invention provides a method of promoting a carbon-sulfur bond forming reaction. In certain embodiments, the reaction comprises cross-coupling of a(n) (hetero)aryl halide with a thiol to form the carbon-sulfur bond, wherein the method is promoted by light irradiation in the absence of a photocatalyst. In other embodiments, the cross-coupling reaction can be promoted through visible light irradiation, including sunlight.
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Paragraph 0097; 0108; 0109
(2019/01/10)
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- Merging Photoredox and Organometallic Catalysts in a Metal–Organic Framework Significantly Boosts Photocatalytic Activities
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Metal–organic frameworks (MOFs) have been extensively used for single-site catalysis and light harvesting, but their application in multicomponent photocatalysis is unexplored. We report here the successful incorporation of an IrIII photoredox catalyst and a NiII cross-coupling catalyst into a stable Zr12 MOF, Zr12-Ir-Ni, to efficiently catalyze C?S bond formation between various aryl iodides and thiols. The proximity of the IrIII and NiII catalytic components to each other (ca. 0.6 nm) in Zr12-Ir-Ni greatly facilitates electron and thiol radical transfers from Ir to Ni centers to reach a turnover number of 38 500, an order of magnitude higher than that of its homogeneous counterpart. This work highlights the opportunity in merging photoredox and organometallic catalysts in MOFs to effect challenging organic transformations.
- Zhu, Yuan-Yuan,Lan, Guangxu,Fan, Yingjie,Veroneau, Samuel S.,Song, Yang,Micheroni, Daniel,Lin, Wenbin
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supporting information
p. 14090 - 14094
(2018/10/15)
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- COMPOSITIONS AND METHODS OF PROMOTING ORGANIC PHOTOCATALYSIS
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The invention provides novel compounds and methods that are useful in promoting reactions that proceed through an oxidative quenching pathway. In certain embodiments, the reactions comprise atom transfer radical polymerization.
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Paragraph 0068; 0219-0220
(2018/09/12)
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- Nickel Phosphite/Phosphine-Catalyzed C-S Cross-Coupling of Aryl Chlorides and Thiols
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A method for the coupling of aryl chlorides and thiophenols using an air-stable nickel(0) catalyst is described. This thioetherification procedure can be effectively applied to a range of electronically diverse aryl/heteroaryl chlorides without more expensive metal catalysts such as palladium, iridium, or ruthenium. This investigation also illustrates both, a variety of thiol coupling partners and, in certain cases, the use of Cs2CO3.
- Jones, Kieran D.,Power, Dennis J.,Bierer, Donald,Gericke, Kersten M.,Stewart, Scott G.
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supporting information
p. 208 - 211
(2018/01/17)
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- C-S cross-coupling reactions catalyzed by a non-symmetric phosphinito-thiophosphinito PSCOP-Ni(II) pincer complex
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A new non-symmetric phosphinito-thiophosphinito POCSP-Ni(II) pincer compound was synthetized and characterized. The molecular structure of [NiCl{C6H3-2-(OPPh2)-6-(SPPh2)}] (1) was unequivocally determined by single crystal X-ray diffraction analysis, showing the Ni center to be located into a slightly distorted square planar geometry. This compound was used as efficient catalyst in C-S couplings of disulfides with iodobenzenes, exhibiting good activity and selectivity as well as tolerance to different functional groups.
- Serrano-Becerra, Juan M.,Valdés, Hugo,Canseco-González, Daniel,Gómez-Benítez, Valente,Hernández-Ortega, Simón,Morales-Morales, David
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p. 3377 - 3380
(2018/08/06)
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- SPS–Ni(II) pincer compounds of the type [Ni(phPS2)(P(C6H4-4-R)3)] Synthesis, characterization and catalytic evaluation in C–S cross-coupling reactions
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The synthesis and characterization of a series of SPS–Ni(II) pincer complexes with different para-substituted triphenylphosphines has been performed. The molecular structure of [Ni(phPS2)(PPh3)] (1) (phPS2H2 = PhP(C6H4-2-SH)2, bis(phenyl-2-thiol)phenylphosphine) was unequivocally determined by single crystal X-ray diffraction analysis. The metal centre exhibited a slightly distorted square planar geometry. The complexes showed a high catalytic activity in the C–S cross-coupling reaction of both alkyl- and aryl-disulfides with iodobenzenes for the production of non-symmetric sulfides. In general, the different para-substituted triphenylphosphine ligands do not affect the catalytic performance of the SPS–Ni(II) complexes. However, activity of the catalyst decreases with the steric hindrance of the different alkyl groups in the disulphide substrates.
- Gómez-Benítez, Valente,Valdés, Hugo,Hernández-Ortega, Simón,Germán-Acacio, Juan Manuel,Morales-Morales, David
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p. 144 - 148
(2017/10/13)
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- Visible-light-promoted C-S cross-coupling via intermolecular charge transfer
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Disclosed is a mild, scalable, visible-lightpromoted cross-coupling reaction between thiols and aryl halides for the construction of C-S bonds in the absence of both transition metal and photoredox catalysts. The scope of aryl halides and thiol partners includes over 60 examples and therefore provides an entry point into various aryl thioether building blocks of pharmaceutical interest. Furthermore, to demonstrate its utility, this C-S coupling protocol was applied in drug synthesis and latestage modifications of active pharmaceutical ingredients. UV-vis spectroscopy and time-dependent density functional theory calculations suggest that visible-lightpromoted intermolecular charge transfer within the thiolate-aryl halide electron donor-acceptor complex permits the reactivity in the absence of catalyst.
- Liu, Bin,Lim, Chern-Hooi,Miyake, Garret M.
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supporting information
p. 13616 - 13619
(2017/11/06)
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- Room-Temperature Arylation of Thiols: Breakthrough with Aryl Chlorides
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The formation of aryl C?S bonds is an important chemical transformation because aryl sulfides are valuable building blocks for the synthesis of biologically and pharmaceutically active molecules and organic materials. Aryl sulfides have traditionally been synthesized through the transition-metal-catalyzed cross-coupling of aryl halides with thiols. However, the aryl halides used are usually bromides and iodides; readily available, low-cost aryl chlorides often not reactive enough. Furthermore, the deactivation of transition-metal catalysts by thiols has forced chemists to use high catalyst loadings, specially designed ligands, high temperatures, and/or strong bases, thus leading to high costs and the incompatibility of some functional groups. Herein, we describe a simple and efficient visible-light photoredox arylation of thiols with aryl halides at room temperature. More importantly, various aryl chlorides are also effective arylation reagents under the present conditions.
- Jiang, Min,Li, Haifang,Yang, Haijun,Fu, Hua
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supporting information
p. 874 - 879
(2017/01/14)
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- Ni nanoparticles on RGO as reusable heterogeneous catalyst: Effect of Ni particle size and intermediate composite structures in C-S cross-coupling reaction
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The present work demonstrates the C-S cross-coupling reaction between aryl halides and thiols using nickel nanoparticles (Ni NPs) supported on reduced graphene oxide (Ni/RGO) as a heterogeneous catalyst. It is observed that the uniformly dispersed Ni NPs supported on RGO could exhibit excellent catalytic activity in C-S cross-coupling reactions and the catalytic application is generalized with diverse coupling partners. Although the electron-rich planar RGO surface helps in stabilizing the agglomeration-free Ni NPs, the catalytic process is found to occur involving Ni(II) species and the recovered catalyst containing both Ni(0)/Ni(II) species is equally efficient in recycle runs. A correlation of loading of Ni species, size of NPs and the intermediate Ni-related heterostructures formed during the catalytic process has been established for the first time, and found to be best in the C-S cross-coupling reaction for Ni(0) and Ni(II) NPs of the average sizes 11-12 nm and 4 nm, respectively.
- Sengupta, Debasish,Bhowmik, Koushik,De, Goutam,Basu, Basudeb
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p. 1796 - 1806
(2017/09/27)
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- Formation of C-C, C-S and C-N bonds catalysed by supported copper nanoparticles
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Transition-metal catalysed cross-coupling reactions are still dominated by palladium chemistry. Within the recent past, copper has gained ground against palladium by virtue of its cheaper price and equivalent function in certain reactions. Four catalysts consisting of copper nanoparticles on zeolite, titania, montmorillonite and activated carbon have been tested in three palladium- and ligand-free cross-coupling reactions to form carbon-carbon, carbon-sulfur and carbon-nitrogen bonds. CuNPs/zeolite has been found to be the best one in the Sonogashira reaction of aryl iodides and arylacetylenes, as well as in the coupling of aryl halides with aryl and alkyl thiols, being reusable in both cases. However, the arylation of nitrogen-containing heterocycles (imidazole, pyrazole, benzimidazole and indole) has been better accomplished with CuNPs/titania, albeit CuNPs/activated carbon showed better recycling properties. The catalytic activity of the nanostructured catalysts has been compared with that of twelve commercial copper catalysts, with the former outperforming the latter in the three types of reactions studied.
- Mitrofanov, Alexander Yu.,Murashkina, Arina V.,Martín-García, Iris,Alonso, Francisco,Beletskaya, Irina P.
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p. 4401 - 4412
(2017/10/13)
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- Copper nanoparticles supported on polyaniline-functionalized multiwall carbon nanotubes: An efficient and recyclable catalyst for synthesis of unsymmetric sulfides using potassium ethyl xanthogenate in water
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A new and powerful polyaniline-functionalized carbon nanotube-supported copper(II) nanoparticle catalyst was successfully prepared and evaluated as a heterogeneous catalyst for the one-pot synthesis of unsymmetric thioethers by coupling of aryl, alkyl and benzyl halides using potassium ethyl xanthogenate as source of sulfur in water. All of these reactions gave the desired products in good to excellent yields. The catalyst is available, air-stable and can be reused several times without significant loss in its catalytic activity.
- Hajipour, Abdol R.,Jajarmi, Saeideh,Khorsandi, Zahra
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- Iron(0) nanoparticles mediated direct conversion of aryl/heteroaryl amines to chalcogenides via in situ diazotization
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A simple procedure for the synthesis of organo-chalcogenides has been developed by the reaction of aryl/heteroaryl amines with di-aryl/heteroaryl dichalcogenides in the presence of tBuONO and Fe(0) nanoparticles. The reaction proceeds via in situ diazotization followed by chalcogenation. A series of functionalized diaryl/aryl heteroaryl/diheteroaryl/aryl-alkyl selenides, sulfides and tellurides have been obtained by this procedure. Significantly, using this procedure 2,4-dinitroaniline is converted to (2,4-dinitrophenyl)(phenyl)selane which is known as thioredoxin reductase (TR) and glutathione reductase (GR) inhibitor. The reaction goes by a radical pathway and a plausible mechanism has been suggested.
- Panja, Subir,Maity, Pintu,Kundu, Debasish,Ranu, Brindaban C.
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supporting information
p. 3441 - 3445
(2017/08/10)
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- Method of preparing diarylthioether
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The invention discloses a method of preparing diarylthioether. In the method, with diarylsulfoxide as a reaction raw material, the diarylthioether is produced through a reaction in a solvent under the effects of an electrophilic reagent and alkali. In the method, the diarylthioether is produced by reducing the diarylsulfoxide, as a substrate, under mild conditions. The method has mild reaction conditions, high selectivity and yield and simple operations. The products are easy to separate.
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Paragraph 0059-0061
(2017/08/31)
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- A general and inexpensive protocol for the Cu-catalyzed C-S cross-coupling reaction between aryl halides and thiols
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A cost effective and easily available CuI/DABCO catalytic system has been developed for C-S cross-coupling reaction. This method is extremely useful for the thioetherification of aryl and heteroaryl halides providing excellent yields and good chemoselectivity.
- Thomas, Anns Maria,Asha, Sujatha,Sindhu,Anilkumar, Gopinathan
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supporting information
p. 6560 - 6564
(2015/11/09)
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- An efficient iron-catalyzed S-arylation of aryl and alkylthiols with aryl halides in the presence of water under aerobic conditions
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Abstract In this study, an environmentally benign FeCl3·6H2O/l-proline catalytic system in the presence of TBAB was employed as a catalyst for the coupling reactions of aryl halides with aryl and alkyl thiols in water under aerobic conditions. The versatility, low cost, and environmental friendliness, in combination with high yields, makes the procedure noteworthy. This protocol offers a simple and efficient thioetherification method for aryl halides.
- Sindhu,Thankachan, Amrutha P.,Thomas, Anns Maria,Anilkumar, Gopinathan
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supporting information
p. 4923 - 4926
(2015/07/28)
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- A novel and efficient zinc-catalyzed thioetherification of aryl halides
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The first zinc-catalysed protocol for the C-S cross-coupling reaction is reported. Zinc catalysis has an undeniable advantage over other catalytic systems as it is non-toxic, and the catalysts are easily available and cheap, with environmentally benign properties. This novel, efficient, palladium- and triphenylphosphine-free protocol yielded a variety of aryl and alkyl sulfides in moderate to excellent yields. This journal is
- Thankachan, Amrutha P.,Sindhu,Krishnan, K. Keerthi,Anilkumar, Gopinathan
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p. 32675 - 32678
(2015/04/27)
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- Microwave-Assisted Copper-Catalyzed Cross-Coupling Reaction of Thiols with Aryl Iodides in Water
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Microwave-promoted C-S bond formation from thiols and aryl iodides in the presence of a copper catalyst is reported. A combination of copper(II) oxide and 1,10-phenanthroline catalyzes this reaction. A variety of aryl iodides react smoothly with thiols to provide the corresponding aryl sulfides in good to excellent yields. Notably, the reactions proceed in water with a short reaction time (30 minutes). This system shows broad functional-group tolerance; amino, chloro, bromo, acetyl, and nitro groups are unaffected by the reaction conditions.
- Chen, Yi-An,Badsara, Satpal Singh,Tsai, Wan-Ting,Lee, Chin-Fa
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p. 181 - 186
(2015/05/04)
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- AROMATIC SULFIDE COMPOUNDS AND METHODS AND USE THEREOF
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Described herein, inter alia, are aromatic sulfide compositions and methods for treating or preventing cancer using the same.
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Paragraph 0168; 0178
(2015/11/03)
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- Copper mediated formation of carbon-heteroatom bonds using organoboron reagents and ultrasound
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This report summarizes research efforts focused on copper acetate mediated reactions to form new carbon-heteroatom bonds using organoboron reagents under ultrasound irradiation. The method involves the application of ultrasound irradiation to the Chan-Evans-Lam reaction to achieve O-arylation of phenols, N-arylation of anilines and indoles, and S-arylation of thiols. Ultrasound irradiation was found to decrease reaction times from 72 hours to 4 hours while improving the product yields an average of 20%.1 Representative C-O, C-N, and C-S coupling reactions were successfully scaled-up from the milligram to gram levels while maintaining good product yields offering potential applications in industrial processes.
- Musolino, Bryan J.,Kabalka, George W.
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p. 271 - 297
(2015/03/04)
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- Sulfur-silicon bond activation catalysed by Cl/Br ions: Waste-free synthesis of unsymmetrical thioethers by replacing fluoride catalysis and fluorinated substrates in SNAr reactions
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In contrast to conventional activation of Nu-SiR3 reagents by F ion attributed to the strong affinity of Si to F, S-Si activation can now be achieved using Cl/Br ions of TBAX as catalysts via formation of weaker X-Si bonds and Me3Si-X. This led to a waste-free synthesis of unsymmetrical thioethers via F-free SNAr reactions of activated (hetero)aryl halides and RS-SiMe3, with recovery of the useful Me3Si-X reagent in high yields. This journal is the Partner Organisations 2014.
- Jia, Xiaojuan,Yu, Lei,Liu, Jianping,Xu, Qing,Sickert, Marcel,Chen, Lianhui,Lautens, Mark
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supporting information
p. 3444 - 3449
(2014/07/08)
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- Diaryl and heteroaryl sulfides: Synthesis via sulfenyl chlorides and evaluation as selective anti-breast-cancer agents
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A mild protocol for the synthesis of diaryl and heteroaryl sulfides is described. In a one-pot procedure, thiols are converted to sulfenyl chlorides and reacted with arylzinc reagents. This method tolerates functional groups including aryl fluorides and chlorides, ketones, as well as N-heterocycles including pyrimidines, imidazoles, tetrazoles, and oxadiazoles. Two compounds synthesized by this method exhibited selective activity against the MCF-7 breast cancer cell line in the micromolar range.
- Yonova, Ivelina M.,Osborne, Charlotte A.,Morrissette, Naomi S.,Jarvo, Elizabeth R.
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p. 1947 - 1953
(2014/04/03)
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- An efficient heterogeneous Cu-grafted mesoporous organosilicas nanocatalyst for two and three component C-S coupling reactions
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Furfural-imine functionalized mesoporous organosilica material has been synthesized by postsynthesis surface functionalization of 2D-hexagnoal mesoporous SBA-15 with organosilane precursor 3-aminopropyltriethoxy-silane (APTES) followed by Schiff-base condensation with furfural. On the other hand, furfural-imine functionalized MCM-41 has been synthesized by Schiff-base condensation of furfural and 3-aminopropyltriethoxy-silane (APTES) followed by its hydrothermal co-condensation with tetraethylorthosilicate (TEOS) in the presence of a cationic surfactant CTAB. Subsequent reaction of the imine-functionalized mesoporous organosilicas with Cu(OAc)2 in absolute ethanol produced Cu(II)-grafted mesoporous nanocatalysts 1 and 2, respectively. Powder XRD, HR TEM, FE SEM, N2 sorption and EPR experimental tolls are employed to characterize these Cu-grafted furfural-imine functionalized nanocatalysts. Cu-grafted MCM-41 (1) showed very good catalytic efficiency for the coupling of aryl bromides and thiophenol under aerobic conditions to produce different thioethers. On the other hand, Cu-anchored mesoporous SBA-15 nanocatalyst (2) exhibited high catalytic activity for one-pot three component coupling of different aryl halides with thiourea and benzyl bromide in aqueous medium to produce different aryl alkyl thioethers in very good yields. Both Cu-grafted mesoporous nanocatalysts can be efficiently reused for several reaction cycles. Copyright
- Mondal, John,Salam, Noor,Bhaumik, Asim
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p. 4883 - 4895
(2013/08/23)
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- Room temperature Ullmann type C-O and C-S cross coupling of aryl halides with phenol/thiophenol catalyzed by CuO nanoparticles
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C-O/C-S cross coupling of aryl halides with phenol or thiophenol was studied under ligand-free condition at room temperature over CuO nanocatalyst. The scope of the reaction was extended to various aryl halides and substituted phenols under optimized condition. In general, efficient, selective, and reusable heterogeneous nano CuO catalytic system has been developed for room temperature C-O and C-S Ullmann type cross coupling reactions.
- Babu, S. Ganesh,Karvembu
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p. 1677 - 1680
(2013/03/28)
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- Nickel-mediated inter- and intramolecular C-S coupling of thiols and thioacetates with aryl iodides at room temperature
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A Ni(0)-catalyzed intermolecular cross-coupling of various functionalized thiols and aryl iodides has been developed and successfully extended to less explored intramolecular versions, where thioacetates could also be utilized as the strategic surrogate. Air-stable precatalysts, very mild conditions, and an easy protocol allow rapid access to medicinally useful aryl thioethers, as demonstrated in the facile synthesis of (±)-chuangxinmycin as a key step.
- Xu, Xiao-Bo,Liu, Jian,Zhang, Jian-Jian,Wang, Ya-Wen,Peng, Yu
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supporting information
p. 550 - 553
(2013/04/11)
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- Efficient synthesis of unsymmetrical diaryl thioethers via TBAF-mediated denitrative substitution of nitroarenes with PhSTMS under mild and neutral conditions
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Tetrabutylammonium fluoride (TBAF) effectively facilitated a denitrative substitution reaction of electron-deficient nitroarenes with phenylthiotrimethylsilane (PhSTMS) under mild and base-free neutral conditions at room temperature, providing a practical and efficient synthesis of useful unsymmetrical diaryl thioethers. Nitroarenes bearing ortho- and para-positioned electron-withdrawing groups are the most reactive substrates, indicating that this reaction most possibly proceeded via the nucleophilic aromatic substitution (SNAr) mechanism.
- Yu, Xiao-Chun,Li, Bo,Yu, Bao-Hua,Xu, Qing
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p. 605 - 608
(2013/07/27)
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- Efficient nickel/N-heterocyclic carbene catalyzed C-S cross-coupling
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The cross-coupling reaction of aryl halides with aliphatic and aromatic thiols catalyzed by readily available Ni(OAc)2 with N-heterocyclic carbene (NHC) is reported. Ni(OAc)2/NHC catalyst showed good activities toward various aryl halides in C-S coupling reaction, even with aryl chlorides. Reactions occurred in excellent yields, broad scope, and high tolerance of functional groups.
- Guan, Pei,Cao, Changsheng,Liu, Yun,Li, Yunfei,He, Pan,Chen, Qian,Liu, Gang,Shi, Yanhui
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supporting information
p. 5987 - 5992,6
(2012/12/12)
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- Efficient nickel/N-heterocyclic carbene catalyzed C-S cross-coupling
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The cross-coupling reaction of aryl halides with aliphatic and aromatic thiols catalyzed by readily available Ni(OAc)2 with N-heterocyclic carbene (NHC) is reported. Ni(OAc)2/NHC catalyst showed good activities toward various aryl halides in C-S coupling reaction, even with aryl chlorides. Reactions occurred in excellent yields, broad scope, and high tolerance of functional groups.
- Guan, Pei,Cao, Changsheng,Liu, Yun,Li, Yunfei,He, Pan,Chen, Qian,Liu, Gang,Shi, Yanhui
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supporting information
p. 5987 - 5992
(2013/01/13)
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