- Magnetically recoverable ferromagnetic 3D hierarchical core-shell Fe3O4@NiO/Co3O4 microspheres as an efficient and ligand-free catalyst for C–S bond formation in poly (ethylene glycol)
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A simple and efficient protocol for the synthesis of diaryl thioethers from the reaction of thiourea with a wide variety of aryl halides, including aryl iodides, aryl bromides and aryl chlorides in the presence of 3D hierarchical core-shell Fe3O4@NiO/Co3O4 microspheres has been described. This reaction enables the one-pot synthesis of diaryl thioethers in good to high yields using a non-toxic and magnetically separable catalyst in PEG-400 as an eco-friendly, safe, inexpensive and thermally stable solvent. Magnetic separation and reusability of catalyst for eight times without any significant loss of activity, the use of a commercially available, eco-friendly, cheap and chemically stable sulfur transfer agent and solvent, operational simplicity, environmentally benign, easier work-up procedure and cost efficiency make this method a promising candidate for potential applications in some organic reactions. The catalytic activity of Fe3O4@NiO/Co3O4 as a novel and inexpensive catalyst was investigated in the C-S cross coupling reaction.
- Vatandoust Namanloo, Ahad,Akhlaghinia, Batool,Mohammadinezhad, Arezou
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- Synthesis of sulfides via reaction of aryl/alkyl halides with S8 as a sulfur-transfer reagent catalyzed by Fe3O4-magnetic-nanoparticles-supported L-Histidine-Ni(II)
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One-pot synthesis of symmetrical diaryl/alkyl sulfides in high yields from the reaction between aryl/alkyl halides and S8 can be carried out in a short period, using Fe3O4@SiO2@His@Ni(II) as a reusable catalyst. The present approach offers the advantages of a clean reaction, simple methodology and high efficiency, and avoids the use of a toxic catalyst.
- Azadi, Gouhar,Taherinia, Zahra,Naghipour, Ali,Ghorbani-Choghamarani, Arash
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- Infrared spectroscopy of bis(4-nitrophenyl) disulfide grown on a Pb layer
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Crystal whiskers of bis(4-nitrophenyl) disulfide have been grown on a 100-nm thick Pb film from a supersaturated solution of p-nitrothiophenol. The whiskers preferentially grow on Pb but not on Si, In, or Ag. The crystals were characterized by electron microscopy and infrared spectroscopy. The optimized structure of the molecule was determined by ab initio calculations.
- McCluskey,Grover,Zhuravlev
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- A novel heterogeneous nanocatalyst: 2-Methoxy-1-phenylethanone functionalized MCM-41 supported Cu(II) complex for C-S coupling of aryl halides with thiourea
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An environmentally friendly copper-based catalyst supported on 2-Methoxy-1-phenylethanone functionalized MCM-41 was prepared and characterized by FT-IR, FE-SEM, TEM, XRD, EDX, BET and ICP techniques. The catalyst was applied for the C?S cross-coupling reaction of aryl halides with thiourea. Corresponding products were produced in good yields in aerobic conditions. The catalyst could be recovered and recycled for several times.
- Hajipour, Abdol R.,Fakhari, Farzaneh,Nabi Bidhendi, Gholamreza
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- An efficient and recyclable catalytic system for carbon–sulfur coupling reaction and synthesis of 5-substituted 1H-tetrazoles
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In this research paper, efficient and economical protocols for the synthesis of symmetrical sulfides and 5-substituted 1H-tetrazoles have been reported using Fe3O4@SBTU@Ni(II) as a heterogeneous and recoverable nanocatalyst. The noticeable features of this catalytic system are: operational simplicity, environmentally benign, easier work-up procedure, green and efficient synthetic entry to excellent yield of products in a high reusability and applicability to various starting materials and, therefore, cost efficiency.
- Ghorbani-Choghamarani, Arash,Moradi, Zahra,Azadi, Gouhar
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- Thiol-free route to diaryl sulfides by Cu catalyzed coupling of sodium thiosulfate with aryl halides
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A method for the synthesis of diaryl sulfides from aryl halides in polyethylene glycol was reported. Inodorous Na2S2O3·5H2O, which is readily available as a stable salt, is an effective source of sulfur in the presence of CuI as catalyst.
- Nowrouzi, Najmeh,Abbasi, Mohammad,Latifi, Hadis
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- A simple, efficient and recyclable catalytic system for carbon-sulfur coupling of aryl halides with thioacetamide
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The carbon-sulfur coupling reaction of aryl halides with thioacetamide using an MCM-41-immobilized bidentate nitrogen copper(I) complex [MCM-41-2N-CuI] as an efficient heterogeneous catalyst is described. Developed catalytic system is found to be effective for the coupling reaction of aryl halides with thioacetamide providing moderate to high yield of diaryl sulfides. This heterogeneous copper catalyst exhibits higher activity than CuI and can be recovered by a simple filtration of the reaction solution and reused for at least 10 consecutive trials without any decreases in activity.
- Cai, Mingzhong,Yao, Ruiya,Chen, Lin,Zhao, Hong
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- A simple and green synthesis of diaryl sulfides catalyzed by an MCM-41-immobilized copper(I) complex in neat water
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The heterogeneous carbon-sulfur bond formation reaction of aryl iodides with potassium thiocyanate was achieved in neat water at 130 C by using 5 mol% MCM-41-immobilized bidentate nitrogen/CuCl complex [MCM-41-2N-CuCl] as catalyst and Cs2CO3 as base, yielding a variety of diaryl sulfides in moderate to high yields. This heterogeneous copper catalyst can be easily prepared by a simple two-step procedure from commercially available and cheap reagents and recovered by a simple filtration and reused for 10 cycles without loss of catalytic activity.
- Cai, Mingzhong,Xiao, Ruian,Yan, Tao,Zhao, Hong
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- CuI anchored onto mesoporous SBA-16 functionalized by aminated 3-glycidyloxypropyltrimethoxysilane with thiosemicarbazide (SBA-16/GPTMS-TSC-CuI): A heterogeneous mesostructured catalyst for: S -arylation reaction under solvent-free conditions
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Herein, we report the novel synthesis of CuI anchored onto a cage-like mesoporous material (SBA-16), which was successfully functionalized by aminated 3-glycidyloxypropyltrimethoxysilane with thiosemicarbazide (SBA-16/GPTMS-TSC-CuI) into an efficient and highly recyclable heterogeneous catalyst. The as-synthesized mesostructured catalyst (SBA-16/GPTMS-TSC-CuI) was comprehensively characterized by different techniques, namely, FT-IR, FIR, SAXRD, XRD, XPS, BET, TEM, FE-SEM, EDX, EDX mapping, TGA, ICP-OES, and CHNS analyses. SBA-16 with a unique "super-cage" structure efficiently controlled the formation of dispersed organic and metal species in the mesoporous channels. These confined nanoparticles with a narrow particle size distribution (3-7 nm) exhibited excellent catalytic activity in the S-arylation reaction without necessitating the use of toxic solvents and/or expensive metal catalysts. Interestingly, the mesoporous catalyst was extremely stable under the reaction conditions and could be easily separated by a simple filtration process and reused for at least seven recycle runs (without any appreciable loss in catalytic activity). Due to the inimitable structure of the abovementioned mesostructured catalyst, the C-S coupling products of aryl halides with S8/thiourea under solvent-free conditions were obtained in good to excellent yields in remarkably reduced reaction times in comparison to those reported in earlier studies.
- Ghodsinia, Sara S.E.,Akhlaghinia, Batool
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- Preparation and Characterization of Ni-Modified Graphene Oxide Complex as an Efficient Catalyst for the Synthesis of Sulfides via Reaction of Arylhalides with S8 or Thiourea
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In this work, complex of Ni-modified graphene oxide was prepared and characterized using FT-IR spectroscopy, SEM, XRD, TGA and ICP-OES techniques. This compound used as an efficient and recoverable catalyst for the C–S coupling reaction using sulfur-transfer reagents (S8 or thiourea). The catalyst was easily separated using a simple filtration and reusable without significant loss of their catalytic efficiency.
- Ghafouri-Nejad, Raziyeh,Hajjami, Maryam,Nejat, Razieh
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- Highly efficient and magnetically separable nano-CuFe2O4 catalyzed S-arylation of thiourea by aryl/heteroaryl halides
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The non-toxic and magnetically separable nano-CuFe2O4 catalyzed synthesis of symmetrical aryl sulfides by the reaction of thiourea with a wide variety of aryl halides, including aryl chlorides has been reported. Excellent yields of products have been obtained under ligand-free conditions and without the use of any expensive catalyst, such as palladium.
- Hajipour, Abdol R.,Karimzadeh, Morteza,Azizi, Ghobad
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- Histidine-functionalized chitosan-Cu(II) complex: A novel and green heterogeneous nanocatalyst for two and three component C-S coupling reactions
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Using a fixing Cu2+ NP reaction on histidine modified chitosan, a novel applicable matrix was successfully prepared and investigated as a heterogeneous nanocatalyst for preparing diaryl sulfides and aryl benzyl thioethers. The Cu(ii)-his@CS nanocatalyst was characterized by FT-IR, CHN, XRD, FE-SEM, TEM, EDX, ICP-AES and TG analysis. This novel copper nanocatalyst was used for two and three component C-S coupling reactions of different aryl halides. The nanocatalyst showed high catalytic activity and reusability in both reactions.
- Hajipour, Abdol Reza,Hosseini, Seyed Mostafa,Jajarmi, Saeideh
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- CuFe2O4 magnetic nanoparticle catalyzed odorless synthesis of sulfides using phenylboronic acid and aryl halides in the presence of S8
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CuFe2O4 magnetic nanoparticles were prepared, characterized and used as a magnetically recoverable nanocatalyst for the one-pot synthesis of phenyl aryl/heteroaryl/benzyl sulfides through the cross-coupling reaction of phenylboronic acid with aryl/heteroaryl/benzyl halides in the presence of S8 as a sulfur source in PEG400 as a reusable solvent at 80 °C. Also, the synthesis of symmetrical sulfides from aryl/heteroaryl halides using S8, KF and Cs2CO3 in PEG400 at 120 °C is described. The magnetic nanocatalyst was recycled up to 6 times with little loss of activity.
- Amiri, Kamran,Rostami, Amin,Rostami, Abed
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- Synthesis of peptide nanofibers decorated with palladium nanoparticles and its application as an efficient catalyst for the synthesis of sulfides: Via reaction of aryl halides with thiourea or 2-mercaptobenzothiazole
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In this work supported Pd nanoparticles on a peptide nanofiber (PdNP-PNF) have been prepared via fabrication of self-assembled woven nanofiber from peptide, subsequently immobilization of palladium nanoparticles on this nanostructural compound. To obtain self-assembled woven nanofiber, we designed and synthesized a peptide using arginine as building block. The C-terminus of amino acid was protected as ethylester. Coupling was mediated by dicyclohexylecarbodiimide-1-hydroxybenzotriazole (DCC-HOBT). TEM, SEM, XRD, ICP and FT-IR techniques were employed to characterize prepared nanofiber materials. In this work, the effect of phosphate buffer solutions pH 8 and pH 11 (isoelectric point of arginine amino acid) on the structure of peptide nanofiber was investigated. Supported Pd nanoparticles on the peptide nanofiber (PdNP-PNF) were applied for the C-S coupling reaction using two different sulfur transfer reagents (thiourea and 2-mercaptobenzothiazole).
- Ghorbani-Choghamarani, Arash,Taherinia, Zahra
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- Copper-catalyzed diastereoselective hydrothioetherification of oxa(aza)benzonorbornadienes
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A novel copper-catalyzed hydrothioetherification of oxa(aza)bicyclic alkenes with potassium thioacetate and aryl or alkyl iodides to synthesize unsymmetrical thioethers has been developed. Notably, the reaction with complete diastereoselectivity went through a syn-selective addition process to give exo-adducts. In addition, this protocol exhibited high efficiency and good functional group tolerance to afford the target thioethers in moderate to good yields. Based on the results of mechanistic investigations, a plausible mechanism was proposed.
- Chen, Donghan,Chen, Shuqi,Lin, Qifu,Tan, Yun,Yang, Dingqiao,Yang, Wen,Yao, Yongqi
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- Core–shell nanostructure (Fe3O4?MCM-41?Cu-P2C) as a highly efficient and recoverable nanocatalyst for the synthesis of polyhydroquinoline, 5-substituted 1H-tetrazoles and sulfides
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Fe3O4 magnetic nanoparticles were used as a core for Cu(II) Schiff base complex functionalized mesoporous MCM-41 shell to provide a core–shell nanostructure (Fe3O4?MCM-41?Cu-P2C). A simple, environmentally friendly, inexpensive, green reaction conditions and efficient procedure for the synthesis of polyhydroquinoline, 5-substituted 1H-tetrazoles and sulfides derivatives using this core–shell nanostructure as an efficient, novel and recoverable nanocatalyst has been described. Fe3O4?MCM-41?Cu-P2C is stable, cost-effective, heterogeneous, easy to handle and recoverable nanocatalyst and can be reused for several consecutive runs without a significant loss of catalytic activity. The catalyst was characterized by fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), powder X-ray diffractometer (XRD), scanning electron microscopy (SEM), atomic absorption spectroscopy (AAS), Brunauer–Emmett–Teller (BET) and vibrating sample magnetometer (VSM) techniques.
- Nikoorazm, Mohsen,Erfani, Zahra
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- Palladium Complex Immobilized on Magnetic Nanoparticles Modified with 2-Aminopyridine Ligand: A Novel and Efficient Recoverable Nanocatalyst for C–S and C–Se Coupling Reactions
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A novel, versatile and efficient magnetically recoverable palladium nanocatalyst [Fe3O4@SiO2/2-aminopyridine-Pd(II)] was fabricated via the immobilization of palladium(II) complex on the surface of magnetic nanoparticles modified with 2-aminopyridine ligand. The structure of the as-fabricated Fe3O4@SiO2/2-aminopyridine-Pd(II) nanocomposite was characterized by a series of spectroscopic techniques including FT-IR, SEM, TEM, EDX, TGA, XRD, VSM and ICP-OES techniques. The Fe3O4@SiO2/2-aminopyridine-Pd(II) nanocomposite was utilized under mild and eco-friendly conditions in C–S and C–Se coupling reactions to afford a vast variety of diaryl sulfides and diaryl selenides with good to excellent yields. This heterogeneous palladium catalyst can be magnetically separated and reused for at least 7 consecutive trials without any reduction in activity. Graphical Abstract: [Figure not available: see fulltext.]
- Lu, Lu,Luo, Jia,Wang, Weiqi,Xu, Xiaoqing,Zhang, Jingzheng
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- Copper based on diaminonaphthalene-coated magnetic nanoparticles as robust catalysts for catalytic oxidation reactions and C-S cross-coupling reactions
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In this work, the immobilization of copper(ii) on the surface of 1,8-diaminonaphthalene (DAN)-coated magnetic nanoparticles provides a highly active catalyst for the oxidation reaction of sulfides to sulfoxides and the oxidative coupling of thiols to disulfides using hydrogen peroxide (H2O2). This catalyst was also applied for the one-pot synthesis of symmetrical sulfidesviathe reaction of aryl halides with thiourea as the sulfur source in the presence of NaOH instead of former strongly basic and harsh reaction conditions. Under optimum conditions, the synthesis yields of sulfoxides, symmetrical sulfides, and disulfides were about 99%, 95%, and 96% respectively with highest selectivity. The heterogeneous copper-based catalyst has advantages such as the easy recyclability of the catalyst, the easy separation of the product and the less wastage of products during the separation of the catalyst. This heterogeneous nanocatalyst was characterized by FESEM, FT-IR, VSM, XRD, EDX, ICP and TGA. Furthermore, the recycled catalyst can be reused for several runs and is economically effective.
- Yarmohammadi, Nasrin,Ghadermazi, Mohammad,Mozafari, Roya
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p. 9366 - 9380
(2021/03/16)
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- Trisaminomethane–cobalt complex supported on Fe3O4 magnetic nanoparticles as an efficient recoverable nanocatalyst for oxidation of sulfides and C–S coupling reactions
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In this work, trisaminomethane–cobalt complex immobilized onto the surface of Fe3O4 magnetic nanoparticles was successfully prepared via a simple and inexpensive procedure. The prepared nanocatalyst was considered a robust and clean nanoreactor catalyst for the oxidation and synthesis of sulfides under green conditions. This ecofriendly heterogeneous catalyst was characterized by Fourier transform infrared spectroscopy, X-ray diffractometry, energy-dispersive X-ray spectroscopy, inductively coupled plasma-atomic emission spectroscopy, thermogravimetric analysis, vibrating sample magnetometry, X-ray mapping, scanning electron microscopy, and transmission electron microscopy techniques. Use of green medium, easy separation and workup, excellent reusability of the nanocatalyst, and short reaction time are some outstanding advantages of this method.
- Ashraf, Muhammad Aqeel,Liu, Zhenling,Peng, Wan-Xi
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- Diamine compound containing sulfoxide-based bridge chain as well as synthesis method and application of diamine compound containing sulfoxide-based bridge chain
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The invention provides a diamine compound containing a sulfoxide-based bridge chain as well as a synthesis method and application of the diamine compound containing the sulfoxide-based bridge chain. Sulfoxide diamine synthesized by the method contains a sulfoxide-based bridge chain structure. The synthesis method has the characteristics of simple synthetic route, mild reaction conditions, highly available reaction raw material source, low cost, few organic solvent use types, capability of reducing environmental pollution to the greatest extent and the like. The diamine compound provided by theinvention has a sulfoxide group in structure; and in the synthesis of a polymer material, the diamine compound can improve the light transmittance of the material, increase the heat resistance and reduce the dielectric constant and water absorption of the material, and therefore, the diamine compound is suitable for synthesizing flexible transparent polyimide or polyamide and other films.
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Paragraph 0032-0033
(2020/10/21)
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- Dechalcogenization of Aryl Dichalcogenides to Synthesize Aryl Chalcogenides via Copper Catalysis
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An application for dechalcogenization of aryl dichalcogenides via copper catalysis to synthesize aryl chalcogenides is disclosed. This approach is highlighted by the practical conditions, broad substrate scope, and good functional group tolerance with several sensitive groups such as aldehyde, ketone, ester, amide, cyanide, alkene, nitro, and methylsulfonyl. Furthermore, the robustness of this methodology is depicted by the late-stage modification of estrone and synthesis of vortioxetine. Remarkably, synthesis of more challenging organic materials with large ring tension under milder conditions and synthesis of some halogen contained diaryl sulfides which could not be synthesized using metal-catalyzed coupling reactions of aryl halogen are successfully accomplished with this protocol.
- Cao, Fei,Chen, Jinhong,Deng, Jiedan,Deng, Xuemei,Hou, Yongsheng,Shao, Xiangfeng,Shi, Tao,Wang, Yongqiang,Wang, Zhen,Wu, Lingxi,Yang, Jinru,Yang, Yuhang
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p. 2707 - 2712
(2020/03/11)
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- DIAMINE COMPOUND, AND POLYIMIDE PRECURSOR AND POLYIMIDE FILM PREPARED BY USING THE SAME
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The present invention disclosed a novel diamine compound including a structure in which a phenylene linker (L) connecting an intramolecular imide ring and the imide ring is bonded to a phenyl ring substituted with -NH-(C=O)- or -O-(C=O)-. A polyimide film prepared by polymerizing the novel diamine compound has not only improved mechanical and thermal properties, but also an excellent refractive index.COPYRIGHT KIPO 2021
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Paragraph 0271-0274
(2020/11/03)
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- Cerium catalyst promoted C-S cross-coupling: Synthesis of thioethers, dapsone and RN-18 precursors
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In this work, we present a novel, efficient and green methodology for the synthesis of thioethers by the C-S cross-coupling reaction with the assistance of [Ce(l-Pro)2]2Ox as a heterogeneous catalyst in good to excellent yields. A scale-up of the protocol was explored using an unpublished methodology for the synthesis of a dapsone-precursor, which proved to be very effective over a short time. The catalyst [Ce(l-Pro)2]2Ox was recovered and it was shown to be effective for five more reaction cycles.
- Tavares Junior, José M. Da C.,Da Silva, Caren D. G.,Dos Santos, Beatriz F.,Souza, Nicole S.,De Oliveira, Aline R.,Kupfer, Vicente L.,Rinaldi, Andrelson W.,Domingues, Nelson L. C.
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supporting information
p. 10103 - 10108
(2019/12/23)
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- Ni-guanidine@MCM-41 NPs: a new catalyst for the synthesis of 4,4?-(arylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ols) and symmetric di-aryl sulfides
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In this work, the surface of mesoporous MCM-41 was modified with guanidine, and then, Nickel particles have become immobilized on its surface (Ni-guanidine@MCM-41NPs). This heterogeneous catalyst has been identified by various techniques including: low-angle X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma, thermal gravimetric analysis and N2 adsorption–desorption measurement isotherms, and its catalytic application was studied in the synthesis of 4,4?-(arylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ol) derivatives and symmetric di-aryl sulfides. The prepared organometallic complex could be isolated, post-reaction, by simple filtration for several consecutive cycles without a notable change in its catalytic activity.
- Filian, Hossein,Ghorbani-Choghamarani, Arash,Tahanpesar, Elham
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p. 2673 - 2681
(2019/07/17)
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- Immobilization of Pd(0) complex on the surface of SBA-15: A reusable catalyst for the synthesis of 5-substituted tetrazoles, sulfides and sulfoxides
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A simple and efficient method for the synthesis of 5-substituted tetrazoles, sulfides and sulfoxides in the presence of Pd(0) complex immobilized on mesoporous SBA-15 as an efficient, recoverable and thermally stable mesostructure has been reported. Also, the prepared mesostructure was characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, X-ray mapping, energy-dispersive X-ray spectroscopy, N2 adsorption and desorption, inductively coupled plasma optical emission spectroscopy and thermal gravimetric analysis. Then, this mesostructured catalyst was applied in the synthesis of 5-substituted tetrazoles, sulfides and sulfoxides. The approach described here offers advantages such as short reaction times, high yield, purity yields, simple and eco- friendly, easy work-up. More importantly, this nanohybrid robust catalyst did not undergo metal leaching and applied several times without any decrease in catalytic activity.
- Tamoradi, Taiebeh,Ghorbani-Choghamarani, Arash,Ghadermazi, Mohammad
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p. 374 - 380
(2018/11/01)
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- Synthesis method of thioether compounds
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The invention discloses a synthesis method of thioether compounds. The method comprises steps as follows: phosphorus trichloride and a solvent with uniformly distributed sulfoxide compounds are mixeduniformly, after mixing, the mixture is subjected to a reaction at the temperature of 20-25 DEG C for 0.5-6 h, and the thioether compounds are obtained, wherein the solvent is acetonitrile. Compared with the prior art, the synthesis method has the advantages that raw materials are cheap and easy to obtain, a reducer is cheap and easy to obtain and store, and a series of thioether compounds can beobtained.
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Paragraph 0122-0126
(2019/08/02)
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- NiFe2O4 as a magnetically recoverable nanocatalyst for odourless C–S bond formation via the cleavage of C–O bond in the presence of S8 under mild and green conditions
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We present green methodologies for one-pot and odourless syntheses of unsymmetric and symmetric diaryl sulfides via C─O bond activation using NiFe2O4 magnetic nanoparticles as a reusable heterogeneous nanocatalyst. The synthesis of unsymmetric sulfides is performed using the cross-coupling reaction of phenolic esters such as acetates, triflates and tosylates with arylboronic acid/S8 or triphenyltin chloride/S8 as thiolating agents in the presence of base and NiFe2O4 magnetic nanoparticles as a catalyst in poly(ethylene glycol) as solvent at 60–85°C. Also, the synthesis of symmetric diaryl sulfides from phenolic compounds using S8 as the sulfur source and NiFe2O4 as catalyst in dimethylformamide at 120°C is described. Using these protocols, the syntheses of various unsymmetric and symmetric sulfides become easier than using the available protocols due to the use of a magnetically reusable bimetallic nanocatalyst and avoiding the use of thiols and aryl halides.
- Atashkar, Bahareh,Rostami, Amin,Rostami, Abed,Zolfigol, Mohammad Ali
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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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- Copper-Catalyzed Production of Diaryl Sulfides Using Aryl Iodides and a Disilathiane
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A disilathiane was found to be a novel S1 source for the copper-catalyzed synthesis of diaryl sulfides using aryl iodides. The reaction of iodoarenes and hexamethyldisilathiane, (Me 3 Si) 2 S, in the presence of a catalytic amount of CuI/1,10-phenanthroline provided various types of diaryl sulfides in good yields.
- Ogiwara, Yohei,Maeda, Hiromu,Sakai, Norio
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supporting information
p. 655 - 657
(2017/11/29)
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- Synthesis of Polyhydroquinoline, 2,3-Dihydroquinazolin-4(1H)-one, Sulfide and Sulfoxide Derivatives Catalyzed by New Copper Complex Supported on MCM-41
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Abstract: A simple, efficient and less expensive protocol for the synthesis of Cu(II) immobilized on MCM-41@Serine has been reported. This nanohybrid material was carefully characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma optical emission spectroscopy, X-ray diffraction, TEM, thermal gravimetric analysis, and N2 adsorption and desorption. The obtained nanostructured compound were also employed as a green, efficient, heterogeneous and reusable catalytic system for the synthesis of polyhydroquinoline, 2,3-dihydroquinazolin-4(1H)-one, sulfide and sulfoxide derivatives. High surface area, convenient recovery and reusability for several times without any significant loss of activity, the use of a commercially available, eco-friendly, cheap and chemically stable reagents, good reaction times, simple practical methodology and ease of use all make Cu(II) immobilized on MCM-41@Serine a promising candidate for potential applications in some organic reactions; makes this protocol both attractive and economically viable. Graphical Abstract: MCM-41 nanostructured was prepared via simple and versatile procedure and directly immobilized with a new type of Cu–serine complex. After characterization of this catalyst, the catalytic activity of this nanostructure compound has been investigated for the synthesis of polyhydroquinoline, 2,3-dihydroquinazolin-4(1H)-one, sulfide and sulfoxide derivatives. [Figure not available: see fulltext.].
- Tamoradi, Taiebeh,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
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p. 857 - 872
(2018/03/01)
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- Synthesis of new zirconium complex supported on MCM-41 and its application as an efficient catalyst for synthesis of sulfides and the oxidation of sulfur containing compounds
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In the present work, we report synthesis of new zirconium complex supported on mesoporous silica by anchoring of adenine on the wall of functionalized MCM-41, then reacted with ZrOCl2. The resultant MCM-41-Adenine-Zr was characterized by FT-IR, XRD, TEM, SEM, TGA, EDX, ICP and BET techniques. It was exhibited that the MCM-41-Adenine-Zr can be used as an efficient and thermally stable nanocatalyst for the oxidation of sulfides, oxidative coupling of thiols and synthesis of sulfides. Moreover, this heterogeneous catalyst can be easily recovered from the reaction mixture by simple filtration and reused for several consecutive cycles without noticeable change in its catalytic activity.
- Tamoradi, Taiebeh,Ghorbani-Choghamarani, Arash,Ghadermazi, Mohammad
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- Fe3O4-AMPD-Pd: A novel and efficient magnetic nanocatalyst for synthesis of sulfides and oxidation reactions
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A novel magnetic nanoparticle was synthesized with effective catalytic properties and recyclable ability. This heterogeneous nanocatalyst was identified using Fourier transform infrared, scanning electron microscopies, X‐ray diffraction, vibrating sample magnetometer, inductively coupled plasma atomic emission spectroscopy and thermogravimetric analysis methods. The nanocatalyst was used for the synthesis of the one-pot C–S coupling synthesis of sulfide in the presence of KOH, S8 as the sulfur source in DMSO as the solvent at 100 °C. Also, the oxidation of sulfides to sulfoxides and oxidative coupling of thiols to disulfides in the presence of the catalyst was tested. The catalyst has unique properties such as ability of magnetic separation from the reaction, high repeatability, and high thermal and chemical stability.
- Tamoradi, Taiebeh,Moeini, Nazanin,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
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p. 104 - 109
(2018/07/29)
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- Zirconium oxide complex anchored on boehmite nanoparticles as highly reusable organometallic catalyst for C–S and C–O coupling reactions
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Boehmite nanoparticles were prepared by a simple and inexpensive procedure in water using commercially available materials without inert atmosphere. Then, the surface of the boehmite nanoparticles was modified using 3-mercaptopropyltrimethoxysilane and subsequently zirconium oxide was supported on the modified surface. Zirconium oxide supported on boehmite nanoparticles (Pr.S-ZrO@boehmite) was characterized using scanning electron microscopy, Fourier transform infrared spectroscopy, thermogravimetric analysis and inductively coupled plasma technique. The catalytic application of Pr.S-ZrO@boehmite was studied in C–O and C–S coupling reactions for synthesis of valuable compounds such as ether and sulfide derivatives. All products were obtained in good to excellent yields and the catalyst could be recovered and reused several times without significant loss of catalytic efficiency. Furthermore, zirconium oxide is rarely used as catalyst for cross-coupling reactions.
- Ghorbani-Choghamarani, Arash,Seydyosefi, Zeinab,Tahmasbi, Bahman
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- Deoxygenation of sulphoxides to sulphides with trichlorophosphane
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An efficient route to deoxygenation of sulphoxides to sulphides with PCl3 under mild reaction condition was developed. PCl3 was used as a reducing agent for the first time to convert sulphoxides to sulphides. The mild conditions, use of cheap and readily available reagent, and broad substrate scope render it a useful strategy for preparing sulphides.
- Zhao, Xia,Zheng, Xiancai,Yang, Bo,Sheng, Jianqiao,Lu, Kui
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p. 1200 - 1204
(2018/02/21)
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- Ligand-free copper-catalysed direct synthesis of diaryl sulfides and diaryl disulfides in wet poly(ethylene glycol)
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An improved protocol has been developed for the one-pot CuI-catalysed preparation of symmetric diaryl sulfides from their available aryl halides in the presence of thiourea as sulfur transfer agent and in the absence of both ligand and organic solvent. This catalytic system was also used for the high-yielding preparation of diaryl disulfides in the presence of C2Cl6 as oxidant.
- Nowrouzi, Najmeh,Abbasi, Mohammad,Latifi, Hadis
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- Anchoring of Cu(II)–vanillin Schiff base complex on MCM-41: A highly efficient and recyclable catalyst for synthesis of sulfides and 5-substituted 1H–tetrazoles and oxidation of sulfides to sulfoxides
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A copper(II)–vanillin complex was immobilized onto MCM-41 nanostructure and was used as an inexpensive, non-toxic and heterogeneous catalyst in the synthesis of symmetric aryl sulfides by the cross-coupling of aromatic halides with S8 as an effective sulfur source, in the oxidation of sulfides to sulfoxides using 30% H2O2 as a green oxidant and in the synthesis of 5-substituted 1H–tetrazoles from a smooth (3?+?2) cycloaddition of organic nitriles with sodium azide (NaN3). The products were obtained in good to excellent yields. This catalyst could be reused several times without loss of activity. Characterization of the catalyst was performed using Fourier transform infrared, energy-dispersive X-ray and atomic absorption spectroscopies, X-ray diffraction, thermogravimetric analysis, and scanning and transmission electron microscopies.
- Khanmoradi, Maryam,Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash
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- The first report on the preparation of peptide nanofibers decorated with zirconium oxide nanoparticles applied as versatile catalyst for the amination of aryl halides and synthesis of biaryl and symmetrical sulfides
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We have reported the preparation of peptide nanofibers decorated with zirconium oxide nanoparticles for the first time as a novel, non-toxic, inexpensive and recyclable catalyst for the amination of aryl halides and synthesis of biaryl and symmetrical sulfides (via reaction of aryl halides with S8 or 2-thiobarbituric acid as sulfur transfer reagents). The structure of the catalyst was studied by Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), thermogravimetric analysis (TGA), atomic absorption spectroscopy (AAS), UV-visible absorption and fluorescence spectroscopy.
- Ghorbani-Choghamarani, Arash,Taherinia, Zahra
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p. 9414 - 9423
(2017/08/29)
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- Copper-Catalyzed C-S Bond Formation via the Cleavage of C-O Bonds in the Presence of S8 as the Sulfur Source
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Useful and applicable methods for one-pot and odorless synthesis of unsymmetrical and symmetrical diaryl sulfides via C-O bond activation are presented. First, a new efficient procedure for the synthesis of unsymmetrical sulfides using the cross-coupling reaction of phenolic esters such as acetates, tosylates, and triflates and with arylboronic acid or triphenyltin chloride as the coupling partners is reported. Depending on the reaction, S 8 /KF or S 8 /NaO t -Bu system is found to be an effective source of sulfur in the presence of copper salts and in poly(ethylene glycol) as a green solvent. Then, the synthesis of symmetrical diaryl sulfides from phenolic compounds by using S 8 as the sulfur source and NaO t -Bu in anhydrous DMF at 120 °C under N 2 is described. By these protocols, the synthesis of a variety of unsymmetrical and symmetrical sulfides become easier than the available protocols in which thiols and aryl halides are directly used for the preparation of the sulfides.
- Rostami, Abed,Rostami, Amin,Ghaderi, Arash,Gholinejad, Mohammad,Gheisarzadeh, Sajedeh
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p. 5025 - 5038
(2017/10/06)
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- Highly efficient and reusable polystyrene-supported copper(II) catalytic system for S-arylation of potassium thiocyanate by aryl halides in water
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An inexpensive, efficient and environmentally friendly copper(II) catalyst supported on polystyrene was successfully synthesized and used as a heterogeneous catalyst for S-arylation of potassium thiocyanate by aryl halides. Also this catalyst could be recovered and reused several times without any noticeable decrease in its catalytic activity. Copyright
- Hajipour, Abdol R.,Jajarmi, Saeideh
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p. 566 - 570
(2016/07/16)
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- Microwave-assisted, metal- and solvent-free synthesis of diaryl thioethers from aryl halides and carbon disulfide in the presence of [DBUH]+[OAc]-
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A microwave-assisted direct coupling between aryl halides and carbon disulfide in ionic liquid [DBUH]+[OAc]- (DBU = 1,8-diazabicyclo-[5.4.0] undec-7-ene) has been developed. The reactions are very efficient, affording the corresponding diaryl thioethers in moderate to high yields. Aryl chlorides could also be reacted with carbon disulfide using this protocol. Moreover, [DBUH]+[OAc]- could be easily recovered and reused for several runs.
- Zhou, Yongsheng
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p. 305 - 307
(2016/07/06)
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- Metal-free catalytic synthesis of diaryl thioethers under mild conditions
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A novel method to synthesize diaryl thioethers from aryl halides and carbon disulfide catalyzed by the 1,8-diazabicyclo[5,4,0]undec-7-enium acetate [DBUH][OAc] ionic liquid (IL) under solvent-free conditions has been developed. This metal-free catalytic system displayed high efficiency for coupling aryl halides with CS2 to deliver thioethers. Compared to the conventional methods, no metal catalyst was needed, instead of which the DBU-based ILs played the catalyst and solvent roles simultaneously. Some reactions were carried out under mild conditions (55 °C, 0.5 h), giving moderate to high yields. Moreover, compared with the rare reports, the reaction of the aryl chlorides and fluorides with CS2 could smoothly react in this catalytic system. The products were easily separated from the ILs which could be reused at least three times. The present method provides an efficient and environment-friendly catalytic approach to synthesize diaryl thioethers.
- Cao, Xian-Ting,Zhang, Peng-Fei,Zheng, Hui
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supporting information
p. 6762 - 6767
(2016/08/10)
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- Efficient Cu-catalyzed one-pot odorless synthesis of sulfides from triphenyltin chloride, aryl halides and S8 in PEG
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A novel method for the Cu(OAc)2 catalyzed synthesis of unsymmetrical sulfides from triphenyltin chloride and aryl halides using S8 as the sulfur source in PEG200 at 60-80°C is reported. Triphenyltin chloride is capable of delivering all of its phenyl groups to the product. Also, the copper catalyzed synthesis of symmetrical diaryl sulfides from aryl halides using S8 is described.
- Rostami, Abed,Rostami, Amin,Iranpoor, Nasser,Zolfigol, Mohammad Ali
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supporting information
p. 192 - 195
(2015/12/30)
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- Selective synthesis of organic sulfides or disulfides by solvent exchange from aryl halides and KSCN catalyzed by NiCl2·6H2O
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A method for selective synthesis of symmetric sulfides or disulfides from the reaction of aryl halides with KSCN by solvent exchange is introduced. Aryl halides were selectively converted to the symmetric disulfides or sulfides in high yields when they are treated with KSCN in the presence of NiCl2·6H2O and DMAP at 140?°C in DMF or poly ethylene glycol (PEG-200) respectively.
- Abbasi, Mohammad,Nowrouzi, Najmeh,Latifi, Hadis
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p. 112 - 117
(2016/09/07)
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- Thioether preparation method
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The invention provides a thioether preparation method. The thioether is prepared according to the reaction formula of a formula (1) or a formula (2), wherein the A1-R1-X1 and the A2-R2-X2 are arylhalostannyl derivatives, no transition metal catalysts are needed in the reaction, heavy metal pollution is avoided, the used sulfur sources (sulfide and elementary substance sulfur) are cheap and easy to obtain, operation is simple and efficient, the reaction condition is mild, the cost is low, safety is high, and the thioether preparation method is suitable for industrial production.
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Paragraph 0045; 0046
(2017/02/28)
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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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- Dithiooxamide as an Effective Sulfur Surrogate for Odorless High-Yielding Carbon-Sulfur Bond Formation in Wet PEG200 as an Eco-Friendly, Safe, and Recoverable Solvent
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In this study, we have employed dithiooxamide, a solid, odorless, and commercially available compound, as a sulfur surrogate for the preparation of dialkyl sulfides from available alkyl halides in high yields. This sulfur transfer agent was also used for a copper-catalyzed high-yielding preparation of diaryl sulfides from their available aryl halides and for the preparation of thia-Michael adducts in high yields. All the reactions were performed under odorless conditions in wet PEG200 (PEG = polyethylene glycol), which is an eco-friendly, safe, and recoverable solvent. The protocols were easily applicable to large-scale operation.
- Firouzabadi, Habib,Iranpoor, Nasser,Gorginpour, Forough,Samadi, Arash
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supporting information
p. 2914 - 2920
(2015/05/04)
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- METHOD FOR PRODUCING 4,4'-DINITRO DIPHENYL SULFIDE
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PROBLEM TO BE SOLVED: To provide a method for producing 4,4'-dinitro diphenyl sulfide which solves a conventional problem such as much amount of by-products and low yield, in a method for producing 4,4'-dinitro diphenyl sulfide by using 4-chloro nitrobenzene as a starting material. SOLUTION: There is provided a method for producing 4,4'-dinitro diphenyl sulfide including a step of reacting a mixture (a) under a temperature range of 60°C or less when producing 4,4'-dinitro diphenyl sulfide by heating the mixture (a) comprising at least 4-chloro nitrobenzene, a sulfidation agent and an organic polar solvent. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0030-0065
(2020/10/16)
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- Synthesis of diaryl thioethers from aryl halides and potassium thiocyanate
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An efficient palladium catalyst was synthesized using nicotine, benzyl chloride and palladium chloride. The structure of this catalyst was characterized and it was then used for the synthesis of diaryl sufides. A variety of diaryl thioethers were synthesized under relatively mild reaction conditions. This protocol avoids foul-smelling thiols via cross-coupling of aryl halides with potassium thiocyanate and all substrates give the corresponding products in good to excellent yields in the presence of low amounts of the catalyst.
- Hajipour, Abdol R.,Pourkaveh, Raheleh,Karimi, Hirbod
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p. 879 - 883
(2015/02/05)
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- A copper-catalyzed synthesis of symmetrical diarylsulfanes
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A room-temperature, copper-catalyzed synthesis of symmetrical diarylsulfanes has been developed. The reaction proceeds from aryl iodides and elemental sulfur (S8) by the action of copper(I) salts in the presence of N-ethyl-N-isopropylpropan-2-amine to afford the corresponding diarylsulfanes in good yields. Georg Thieme Verlag Stuttgart New York.
- Yavari, Issa,Ghazanfarpour-Darjani, Majid,Solgi, Yazdan
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p. 1121 - 1123
(2014/05/20)
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- PROCESS FOR THE PREPARATION OF SULFONAMIDE COMPOUNDS
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Process for the preparation of known sulfonamides having antibacterial activity applicable on industrial scale, which allows their production in high yields and purity, comprising in particular the step of nucleophile aromatic substitution and oxidation in suitable conditions.
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Paragraph 0045
(2014/10/16)
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- Use of base control to provide high selectivity between diaryl thioether and diaryl disulfide for C-S coupling reactions of aryl halides and sulfur and a mechanistic study
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Previous studies have reported that S-arylation produces diaryl disulfide when the precursors include sulfur powder and aryl halide using CuI as the catalyst. However, our research has revealed that the use of different bases in the above S-arylation process results in the coproduction of diarylsulfane and diaryldisulfane. In addition, we have demonstrated that the ratio of the two products can be controlled by selecting the alkalinity of the bases. 1H NMR spectra showed that diaryldisulfane was the first product, which became the reagent in a reaction with aryl halide to form diarylsulfane through CuI catalysis. Various aryl halides were tested to enhance the selectivity between diarylsulfane and diaryldisulfane using various different bases, leading to the following principles. A weak base, such as metal carbonate or acetate, results in the production of only diaryldisulfane; a strong base, such as metal hydroxide, results in the production of both diaryldisulfane and diarylsulfane. According to DFT calculations, hydroxide ions, which were exchanged for iodide and bonded with Cu, affected Cu electrons more strongly to reduce diaryl disulfide.
- Chen, Hsing-Ying,Peng, Wei-Te,Lee, Ying-Hsien,Chang, Yu-Lun,Chen, Yen-Jen,Lai, Yi-Chun,Jheng, Nai-Yuan,Chen, Hsuan-Ying
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p. 5514 - 5522
(2013/11/06)
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