- CsOH·H2O-promoted synthesis of aryl sulfides via direct coupling of aryl halides and thiols
-
We report here our observation that, using appropriate reaction conditions, CsOH·H2O-promoted coupling of aryl halides with thiols can be performed in moderate to good yields without a transition metal catalyst. Copyright
- Varala, Ravi,Ramu,Mujahid Alam,Adapa, Srinivas R.
-
-
Read Online
- A facile method for the synthesis of copper modified amine-functionalized mesoporous zirconia and its catalytic evaluation in C-S coupling reaction
-
A new copper modified amine functionalized zirconia has been synthesized by a co-condensation method using zirconium butoxide and aminopropyltriethoxy- silane (APTES) in the presence of a cationic surfactant CTAB followed by impregnation of copper. Nitrogen adsorption-desorption, X-ray powder diffraction, Fourier-transform infrared spectroscopy (FT-IR), 13C nuclear magnetic resonance (NMR), scanning electron micrography (SEM), transmittance electron micrography (TEM), thermo gravimetric analysis-differential thermal analysis (TGA-DTA), X-ray photoelectron spectroscopy (XPS) and UV-vis DRS spectroscopic tools are used to characterize the materials. FT-IR and DRS results indicated the incorporation of Cu and amino groups on the surface of zirconia. This Cu-anchored mesoporous material acts as an efficient, reusable catalyst in the aryl-sulfur coupling reaction between aryl iodide and thiophenol for the synthesis of value added diarylsulfides.
- Mallick, Sujata,Rana, Surjyakanta,Parida, Kulamani
-
-
Read Online
- Environmentally Friendly and Recyclable CuCl 2-Mediated C-S Bond Coupling Strategy Using DMEDA as Ligand, Base, and Solvent
-
Simple reaction conditions and recyclable reagents are crucial for environmentally friendly industrial applications. An environment-friendly, recyclable and economic strategy was developed to synthesize diaryl chalcogenides by the CuCl2-catalyzed C S bondformation reaction via iodobenzenes and benzenethiols/1,2-diphenyldisulfanes using N,N'-dimethylethane-1,2-diamine (DMEDA) as ligand, base, and solvent. For these reactions, especially the reactions of diiodobenzenes and aminobenzenethiols/disulfanediyldianilines, a range of substrates are compatible and give the corresponding products in good to excellent yields. Both of the reagents in the catalytic system (CuCl2/DMEDA) are inexpensive, conveniently separable, and recyclable for more than five cycles.
- Shen, Guodong,Lu, Qichao,Wang, Zeyou,Sun, Weiwei,Zhang, Yalin,Huang, Xianqiang,Sun, Manman,Wang, Zhiming
-
supporting information
p. 184 - 198
(2021/09/20)
-
- Development and Application of Efficient Ag-based Hydrogenation Catalysts Prepared from Rice Husk Waste
-
The development of strategies for the sustainable management and valorization of agricultural waste is of outmost importance. With this in mind, we report the use of rice husk (RH) as feedstock for the preparation of heterogeneous catalysts for hydrogenation reactions. The catalysts were prepared by impregnating the milled RH with a silver nitrate solution followed by carbothermal reduction. The composition and morphology of the prepared catalysts were fully assessed by IR, AAS, ICP-MS, XPS, XRD and STEM techniques. This novel bio-genic silver-based catalysts showed excellent activity and remarkable selectivity in the hydrogenation of nitro groups in both aromatic and aliphatic substrates, even in the presence of reactive functionalities like halogens, carbonyls, borate esters or nitriles. Recycling experiments showed that the catalysts can be easily recovered and reused multiple times without significant drop in performance and without requiring re-activation.
- Unglaube, Felix,Kreyenschulte, Carsten Robert,Mejía, Esteban
-
p. 2583 - 2591
(2021/04/09)
-
- Efficient hydrogenation catalyst designing via preferential adsorption sites construction towards active copper
-
Based on the experimental and DFT calculation results, here for the first time we built preferential adsorption sites for nitroarenes by modification of the supported Cu catalysts surface with 1,10-phenathroline (1,10-phen), by which the yield of aniline via reduction of nitroarene is enhanced three times. Moreover, a macromolecular layer was in-situ generated on supported Cu catalysts to form a stable macromolecule modified supported Cu catalyst, i.e., CuAlOx-M. By applying the CuAlOx-M, a wide variety of nitroarene substrates react smoothly to afford the desired products in up to > 99% yield with > 99% selectivity. The method tolerates a variety of functional groups, including halides, ketone, amide, and C = C bond moieties. The excellent catalytic performance of the CuAlOx-M can be attributed to that the 1,10-phen modification benefits the preferential adsorption of nitrobenzene and slightly weakens adsorption of aniline on the supported nano-Cu surface.
- Dai, Xingchao,He, Dongcheng,Li, Teng,Shi, Feng,Wang, Hongli,Wang, Tao,Wang, Xinzhi
-
p. 397 - 406
(2021/07/21)
-
- Flavin/I2 catalyzed aerobic oxidative C–H sulfenylation of anilines
-
A flavin/I2 catalyzed aerobic oxidative C–H sulfenylation of anilines with thiols under mild reaction conditions is presented for the first time. This metal-free reaction provides an atom-economic pathway to prepare various aryl sulfides with outstanding functional group compatibility. Moreover, it consumes molecular oxygen as the only terminal oxidant and produces environmentally-friendly H2O as the only byproduct.
- Jiang, Xinpeng,Shen, Zhifeng,Zheng, Cong,Fang, Liyun,Chen, Keda,Yu, Chuanming
-
supporting information
(2020/07/24)
-
- TBAI-mediated sulfenylation of arenes with arylsulfonyl hydrazides in DPDME
-
An efficient TBAI (tetrabutylammonium iodide)-mediated C–H sulfenylation of arenes with arylsulfonyl hydrazides in dipropylene glycol dimethyl ether (DPDME) was described. Various electron-rich arenes were applicable in the reaction, such as naphthylamine, naphthol, aniline, indole, pyrrole, and imidaz o [1,2-a] pyridine. A wide range of the aryl sulfides were obtained with good functional group tolerance. This method features green reaction conditions (odorless and easily available sulfur reagent, recyclable TBAI, and DPDME as solvent), and broad substrate scope. The synthetic potential is demonstrated by gram-scale synthesis and downstream transformations. The mechanism studies show that the reaction is achieved through electrophilic substitution process, and diaryl disulfide may be the main intermediate.
- Jie, Zhang,Jing, He,Ping, Liu,Xuezhen, Li,Yali, Liu,Yueting, Wei
-
supporting information
(2020/10/13)
-
- A Robust Pd-Catalyzed C-S Cross-Coupling Process Enabled by Ball-Milling
-
An operationally simple mechanochemical C-S coupling of aryl halides with thiols has been developed. The reaction process operates under benchtop conditions without the requirement for a (dry) solvent, an inert atmosphere, or catalyst preactivation. The reaction is finished within 3 h. The reaction is demonstrated across a broad range of substrates; the inclusion of zinc metal has been found to be critical in some instances, especially for coupling of alkyl thiols.
- Browne, Duncan L.,Jones, Andrew C.,Nicholson, William I.,Smallman, Harry R.
-
supporting information
p. 7433 - 7438
(2020/10/09)
-
- Preventing Pd-NHC bond cleavage and switching from nano-scale to molecular catalytic systems: Amines and temperature as catalyst activators
-
Many reactions catalyzed by Pd complexes with N-heterocyclic carbene (NHC) ligands are performed in the presence of amines which usually act as coupling reagents or mild bases. However, amines can react with Pd/NHC complexes in a number of ways: enhancing molecular catalysis, causing the catalyst deactivation or triggering the ligandless modes of catalysis by producing NHC-free active palladium species. This study gains insight into conditions required for the efficient use of amines as activators of molecular Pd/NHC catalysis and preventing the undesirable reductive cleavage of the Pd-NHC bond in catalytic systems. Reactions of Pd/NHC complexes with various amines within a temperature range of 25-140 °C and thermal stability of the resulting amino-complexes are examined. The results indicate the major influence of the amine structure and reaction temperature on the catalyst transformation. In particular, thermal decomposition of Pd/NHC complexes with aliphatic amine ligands predominantly leads to reductive Pd-NHC bond cleavage, while deprotonation of the complexes with primary and secondary aliphatic amine ligands in the presence of strong bases at 25-60 °C promotes the activation of molecular Pd/NHC catalysis. Efficient Pd-PEPPSI complex-amine systems suitable for strong-base-promoted C-S cross-coupling reactions between aryl halides and thiols are suggested on the basis of these findings.
- Ananikov, Valentine P.,Astakhov, Alexander V.,Chernenko, Andrey Yu.,Chernyshev, Victor M.,Khazipov, Oleg V.,Pasyukov, Dmitry V.,Shevchenko, Maxim A.,Tafeenko, Victor A.
-
p. 1228 - 1247
(2020/03/26)
-
- HETEROCYCLIC COMPOUNDS FOR THE TREATMENT OF EPILEPSY
-
The present invention provides a novel heterocyclic compound represented by Formula [I] and a salt thereof: wherein the symbols are as defined in the specification, which is useful for treating, preventing and/or diagnosing seizure and the like in disease involving epileptic seizure or convulsive seizure (including multiple drug resistant seizure, refractory seizure, acute symptomatic seizure, febrile seizure and status epilepticus), as well as a medical use therefor.
- -
-
Paragraph 0135; 0143; 0144
(2020/06/19)
-
- New arylselanylpyrazole-copper catalysts: Highly efficient catalytic system for C–Se and C–S coupling reactions
-
We describe herein the use of arylselanylpyrazole–copper complexes as versatile catalysts for C–Se and C–S coupling reactions. The performance of these complexes for C–Se reactions was investigated in chalcogenoacetylene synthesis. The reactions were carried out under mild and aerobic conditions and afforded selanylalkynes bearing a variety of electron-withdrawing and electron-donating groups. The performance of these catalysts for C–S coupling was investigated through the reaction of aryl halides with thiols and products were obtained in moderate to excellent yields. A plausible mechanism for selenoacetylene synthesis is also suggested, and the 77Se NMR results show that these arylselanylpyrazole ligands act as hemilabile ligands. High-resolution mass spectrometry was used to investigate the intermediates and also to corroborate the proposed catalytic cycle.
- Coelho, Felipe Lange,Dresch, Lucielle Codeim,Stieler, Rafael,Campo, Leandra Franciscato,Schneider, Paulo Henrique
-
-
- Surfactant-Type Catalyst for Aerobic Oxidative Coupling of Hydrazine with Thiol in Water
-
A series of PEG-functionalized nitrogen ligands were developed to conduct an aerobic oxidative cross-coupling reaction between alkyl- or aryl-hydrazines with thiols in water. This surfactant-type catalyst enables high efficiencies and selectivities, while tolerating a large variety of functional groups. The mother liquor is still catalytically active after five runs.
- Ren, Xuanhe,Tang, Shanyu,Li, Longjia,Li, Jiao,Liang, Helong,Li, Ganzhong,Yang, Guanyu,Li, Heng,Yuan, Bingxin
-
p. 8683 - 8690
(2019/07/08)
-
- Method for synthesizing asymmetric sulfide from molecular oxygen oxidation water phase under catalysis of water-soluble transition metal compound
-
Aiming at problems that in the prior art organic solvent pollution can be caused and a great number of reaction byproducts are generated when asymmetric sulfides are prepared, the invention disclosesa method for synthesizing an asymmetric sulfide from a molecular oxygen oxidation water phase under catalysis of a water-soluble transition metal compound. The method comprises the following steps: dispersing a sulfydryl compound and a hydrazine compound as substrates in a mole ratio of 1:1 into an alkali solution, and at 40-100 DEG C, in the presence of oxygen, and with a water-soluble transitionmetal compound as a catalyst, stirring to carry out reactions, thereby obtaining the asymmetric sulfide. By adopting the method, molecular oxygen is adopted as an oxidant, and water is adopted as a solvent, so that an organic solvent is avoided, a high yield can be achieved, and the problem of byproducts can be generally avoided.
- -
-
Paragraph 0073-0076
(2019/07/29)
-
- Crystallographic and SAR analyses reveal the high requirements needed to selectively and potently inhibit SIRT2 deacetylase and decanoylase
-
A high-quality X-ray crystal structure reveals the mechanism of compound 1a inhibiting SIRT2 deacetylase and decanoylase. Structure-activity relationship (SAR) analysis of the synthesized derivatives of 1a reveals the high requirements needed for selectiv
- Yang, Ling-Ling,Xu, Wei,Yan, Jie,Su, Hui-Lin,Yuan, Chen,Li, Chao,Zhang, Xing,Yu, Zhu-Jun,Yan, Yu-Hang,Yu, Yamei,Chen, Qiang,Wang, Zhouyu,Li, Lin,Qian, Shan,Li, Guo-Bo
-
supporting information
p. 164 - 168
(2019/01/30)
-
- CoII immobilized on an aminated magnetic metal-organic framework catalyzed C-N and C-S bond forming reactions: A journey for the mild and efficient synthesis of arylamines and arylsulfides
-
In this work, we report a simple and versatile method for the modification of a metal-organic framework (NH2-MIL53(Al)) in a step-wise manner. To characterize the synthesized nanostructured catalyst, a variety of spectroscopic and microscopic techniques including FT-IR, XRD, BET, TEM, FE-SEM, EDX, EDX-mapping, TGA, XPS, VSM, ICP-OES and CHN have been employed. Fe3O4@AMCA-MIL53(Al)-NH2-CoII NPs, which benefit from small nanocrystalline size (10-30 nm, according to the XRD and TEM data) in combination with the coexistence of magnetic nanoparticles, a metal-organic framework, and cobalt species, were found to be an excellent environment catalyst to promote the C-N and C-S cross coupling reactions. A wide range of functional substrates including electron-withdrawing and electron-donating aryl halides underwent the coupling reaction with aromatic/heteroaromatic/benzylic and aliphatic amines and sulfides. The results demonstrated that the yields of the target products were good to excellent and the catalyst can be recycled for at least seven recycling runs without a discernible decrease in its catalytic activity. Furthermore, the heterogeneity studies (such as hot filtration and poisoning tests) efficiently confirmed that the as-synthesized nanostructured catalyst is heterogeneous and completely stable under the reaction conditions. We hope that our study inspires more interest in designing novel catalysts based on using low-cost metal ions (such as cobalt) in the field of cross coupling reactions.
- Mohammadinezhad, Arezou,Akhlaghinia, Batool
-
p. 15525 - 15538
(2019/10/19)
-
- Achieving Nickel Catalyzed C-S Cross-Coupling under Mild Conditions Using Metal-Ligand Cooperativity
-
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.
-
p. 4072 - 4085
(2019/04/01)
-
- AGRICULTURAL CHEMICALS
-
The present invention relates to picolinic acid derivatives that are useful in treating fungal diseases ofplants.
- -
-
Page/Page column 59; 110
(2019/08/08)
-
- Site-Selective C?S Bond Formation at C?Br over C?OTf and C?Cl Enabled by an Air-Stable, Easily Recoverable, and Recyclable Palladium(I) Catalyst
-
This report widens the repertoire of emerging PdI catalysis to carbon–heteroatom, that is, C?S bond formation. While Pd0-catalyzed protocols may suffer from the formation of poisonous sulfide-bound off-cycle intermediates and lack of selectivity, the mechanistically diverse PdI catalysis concept circumvents these challenges and allows for C?S bond formation (S–aryl and S–alkyl) of a wide range of aryl halides. Site-selective thiolations of C?Br sites in the presence of C?Cl and C?OTf were achieved in a general and a priori predictable fashion. Computational, spectroscopic, X-ray, and reactivity data support dinuclear PdI catalysis to be operative. Contrary to air-sensitive Pd0, the active PdI species was easily recovered in the open atmosphere and subjected to multiple rounds of recycling.
- Scattolin, Thomas,Senol, Erdem,Yin, Guoyin,Guo, Qianqian,Schoenebeck, Franziska
-
supporting information
p. 12425 - 12429
(2018/09/18)
-
- Modified conditions for copper-catalyzed ipso-thiolation of arylboronic acid esters with thiosulfonates
-
An efficient ipso-thiolation of arylboronic acid esters with thiosulfonates has been achieved under mild and odorless conditions using a copper catalyst. The use of TMEDA and cesium fluoride as the ligand and base, respectively, dramatically facilitated the desired transformation. The method exhibited a broad substrate scope, which allowed for the expeditious synthesis of diverse aryl sulfides from easily available starting materials.
- Kanemoto, Kazuya,Yoshida, Suguru,Hosoya, Takamitsu
-
-
- Nickel Phosphite/Phosphine-Catalyzed C-S Cross-Coupling of Aryl Chlorides and Thiols
-
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.
-
supporting information
p. 208 - 211
(2018/01/17)
-
- C-S cross-coupling reactions catalyzed by a non-symmetric phosphinito-thiophosphinito PSCOP-Ni(II) pincer complex
-
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
-
p. 3377 - 3380
(2018/08/06)
-
- PHOTOCATALYST-FREE, LIGHT-INDUCED CARBON-SULFUR CROSS-COUPLING METHODS
-
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.
- -
-
Paragraph 0098; 0135; 0136
(2019/01/10)
-
- Regioselective thiolation of electron rich arenes and heterocycles in recyclable catalytic media
-
A convenient and novel approach has been developed for the synthesis of unsymmetrical diaryl sulfides by the reaction of sulfonyl hydrazides with phenols using a [Bmim][Br] ionic liquid through the formation of C-S bonds. The reaction has further been extended to indole, β-naphthol and aromatic amine moieties. This protocol offers a new, versatile and greener approach for thiolation of natural phenols (monoterpenes)/aromatic phenols/β-naphthols/aromatic amines and indoles without using any catalyst. A broad range of functional groups were well tolerated in this reaction system.
- Raghuvanshi, Dushyant Singh,Verma, Narsingh
-
p. 22860 - 22868
(2017/07/10)
-
- N-(4-substituted phenyl)-2-substituted acetamide compound and is use as SIRT2 protein inhibitor
-
The invention discloses a compound shown in the formula I or its pharmaceutically acceptable salt, crystalline form and solvate. X represents a group shown in the description, Y represents a group shown in the description, R1, R2 and R3 independently represent H, hydroxyl, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl or phenyl, and R4 represents aryl, heteroaryl, substituted aryl or substituted heteroaryl. The novel compound shown in the formula I has good inhibition activity to SIRT2 and tumors, has a good medicinal value and provides a novel potential choice for clinical medication.
- -
-
Paragraph 0181; 0182
(2017/08/02)
-
- Visible-light-promoted C-S cross-coupling via intermolecular charge transfer
-
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.
-
supporting information
p. 13616 - 13619
(2017/11/06)
-
- CuI/Oxalic Diamide-Catalyzed Cross-Coupling of Thiols with Aryl Bromides and Chlorides
-
We report a general copper-catalyzed cross-coupling of thiols with aryl halides by using N-aryl-N′-alkyl oxalic diamide (L3) or N,N′-dialkyl oxalic diamide (L5) as the ligand. Both aryl and alkyl thiols can be coupled with unactivated aryl bromides and chlorides to give the desired products in good yields. Furthermore, this system features a broad substrate scope and good tolerance of functional groups. Importantly, the oxalic diamides are stable and can be prepared easily from commercially available and cheap starting materials.
- Chen, Chia-Wei,Chen, Yi-Ling,Reddy, Daggula Mallikarjuna,Du, Kai,Li, Chao-En,Shih, Bo-Hao,Xue, Yung-Jing,Lee, Chin-Fa
-
supporting information
p. 10087 - 10091
(2017/08/01)
-
- SINGLE-STEP SYNTHESIS METHOD OF ARYL THIOL AND APPLICATION THEREOF
-
The present invention relates to a single-step synthesis method of aryl thiol, and more specifically, to a method of synthesizing aryl thiol in a single-step by making aryl halide react with alkane dithiol in the presence of a transition metal catalyst. According to the present invention, a single-step synthesis method using the transition metal catalyst, the synthesis method which is capable of synthesizing aryl thiol from aryl halide at a high yield, can be provided. Various aryl halides may be applied to the synthesis method. Further, the synthesis method has advantages that an easily usable reagent may be used, operations are simple, and reactions can be performed under mild conditions. In addition, the synthesized aryl thiol may be used in the synthesis of advanced molecules such as diaryl sulfides and benzothiophenes.COPYRIGHT KIPO 2017
- -
-
Paragraph 0038; 0039; 0083; 0087; 0089; 0091
(2017/09/02)
-
- Pd-PVP-Fe (palladium-poly(N-vinylpyrrolidone)-iron) catalyzed S-arylation of thiols with aryl halides in aqueous media
-
Pd-PVP-Fe (palladium-poly(N-vinylpyrrolidone)-iron) nano catalyst catalyzes selective C–S cross-coupling (S-arylation) reactions of thiols with aryl halides and avoids the formation of S–S (disulfide) homocoupling byproducts. The reactions were carried out in aqueous media using only 0.23?mol% palladium with high selectivity and short reaction time. The effects of the Pd0and Fe0moieties on the C–S cross-coupling reaction mechanism, yield, and selectivity were investigated. The yield and selectivity can be controlled by adjusting the order of adding the reactants and catalyst into the reaction medium. The X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM), electron backscatter diffraction (EBSD) microscopy, energy dispersive X-ray (EDX) spectroscopy, and thermal gravimetric analysis (TGA) tools were used to characterize the catalyst. The C–S cross-coupling reaction process could be repeated up to six times without losing effectiveness. The metals leaching of Pd-PVP-Fe nanocatalyst after reusing cycles were investigated by atomic absorption spectroscopic (AAS) and EDX spectroscopy. The nature of Pd metal after the first run of the C–S cross-coupling reaction was studied by UV–vis spectrophotometry. The morphology of bimetallic nanocatalyst after the first run of the C–S cross-coupling reaction was investigated by SEM, EBSD, and EDX microscopy.
- Ghaderi-Shekhi Abadi, Parvaneh,Rafiee, Ezzat,Joshaghani, Mohammad
-
p. 162 - 170
(2016/07/25)
-
- Polystyrene resin-supported CuI-cryptand 22 complex: a highly efficient and reusable catalyst for the formation of aryl–sulfur bonds in aqueous media
-
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
-
supporting information
p. 1625 - 1628
(2018/03/29)
-
- Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol
-
A highly efficient transition metal-catalyzed single-step synthesis of aryl thiols from aryl halides has been developed employing copper(II) catalyst and 1,2-ethanedithiol. The key features are use of readily available reagents, a simple operation, and relatively mild reaction conditions. This new protocol shows a broad substrate scope with excellent functional group compatibility. A variety of aryl thiols are directly prepared from aryl halides in high yields. Furthermore, the aryl thiols are used in situ for the synthesis of more advanced molecules such as diaryl sulfides and benzothiophenes.
- Liu, Yajun,Kim, Jihye,Seo, Heesun,Park, Sunghyouk,Chae, Junghyun
-
supporting information
p. 2205 - 2212
(2015/07/27)
-
- Arylthiolation of arylamine derivatives with (arylthio)-pyrrolidine-2,5-diones
-
A simple and efficient method for arylthiolation of arylamines has been developed. The protocol uses (arylthio)pyrrolidine-2,5-diones as the arylthiolating reagents, acetonitrile as the solvent, and no catalyst and additive are required, which avoids contamination from the transition metal catalysts in the target products. Therefore, the present method should provide a convenient, efficient and practical strategy for the synthesis of other aryl sulfides.
- Tian, Hua,Yang, Haijun,Zhu, Changjin,Fu, Hua
-
supporting information
p. 481 - 488
(2015/03/05)
-
- Polymethylhydrosiloxane derived palladium nanoparticles for chemo- and regioselective hydrogenation of aliphatic and aromatic nitro compounds in water
-
Chemo- and regioselective hydrogenation of a wide range of aliphatic, unsaturated, aromatic and heteroaromatic nitro compounds into their corresponding amines has been achieved with highly efficient polysiloxane-stabilised "Pd" nanoparticles on NAP-magnesium oxide supports using an environmentally friendly hydrogenating agent, polymethylhydrosiloxane [PMHS] in water. Highly stable and active Pd nanoparticles were prepared by the reduction of NAP-Mg-PdCl4 with PMHS, which serves as a reducing agent as well as a capping agent. The well-dispersed palladium nanoparticles on NAP-MgO catalysts also exhibit excellent regioselectivity in the hydrogenation of dinitrobenzenes to the corresponding nitroanilines. The catalyst has high durability against sintering during the hydrogenation reaction and can be reused with no loss in its activity. This journal is the Partner Organisations 2014.
- Damodara, Dandu,Arundhathi, Racha,Ramesh Babu, T. Venkata,Legan, Margaret K.,Kumpaty, Hephzibah J.,Likhar, Pravin R.
-
p. 22567 - 22574
(2014/06/23)
-
- Copper oxide nanoparticles supported on graphene oxide-Catalyzed S-arylation: An efficient and ligand-free synthesis of aryl sulfides
-
Copper oxide nanoparticles that are supported on graphene oxide as a catalytic system have been utilized for ligand-free and solvent-free C-S cross-coupling reactions with weak bases such as tri- ethylamine. Symmetrical/unsymmetrical aryl sulfides have been synthesized by the coupling of different aryl halides with aromatic as well as aliphatic sulfides. Surprisingly, aryl chlorides also well reacted with different types of sulfides in the presence of dimethyl sulfoxide and cesium carbonate. Besides, this catalytic system is suitable for the synthesis of phenothiazines via cascade C-S and C-N cross-coupling of ortho-dihalides and ortho-aminobenzothiazoles. In addition, this alternative approach is extremely useful for the synthesis of a variety of symmetrical diaryl sulfides by using thiourea as a sulfur source that is devoid of the foul smell of thiols. Indeed, the calculated E-factor value of our present protocol is 2.52. Furthermore, this protocol is particularly attractive as an environmentally benign and practical method for the synthesis of different aryl sulfides. Moreover, the heterogeneous catalytic system described in this process represents not only a greener approach but retains its significant activity for up to six catalytic cycles.
- Kamal, Ahmed,Srinivasulu, Vunnam,Murty,Shankaraiah, Nagula,Nagesh, Narayana,Reddy, T. Srinivasa,Subba Rao
-
p. 2297 - 2307
(2013/10/01)
-
- High surface and magnetically recoverable mPANI/pFe3O 4 nanocomposites for C-S bond formation in water
-
A high surface area mPANI/pFe3O4 nanocomposite from mesoporous polyaniline and porous magnetic Fe3O4 was used as a catalyst in the S-arylation of thiophenol with aryl chlorides and in the C-S bond formation between aryl iodides and thiourea in water. The mesoporosity of the polyaniline enhances the efficiency and stability of the porous magnetic Fe3O4 nanoparticles in both coupling reactions. The mPANI/pFe3O4 nanocomposite can be recovered with an external magnet and reused several times due to the superparamagnetic nature of the porous Fe3O4 nanoparticles.
- Damodara,Arundhathi,Likhar, Pravin R.
-
p. 797 - 802
(2013/04/10)
-
- A general rhodium-catalyzed cross-coupling reaction of thiols with aryl iodides
-
The general procedure for the rhodium-catalyzed cross-coupling of thiols with aryl iodides is described. The catalytic system consists of 5 mol % of [RhCl(cod)]2 and 10 mol % of PPh3 as a ligand. A variety of aryl iodides reacted with thiols, giving aryl thioethers in good to excellent yields. It is important to note that the deactivated aryl iodides such as 4-iodoanisole is worked smoothly to provide the corresponding aryl thioethers in excellent yields. Functional groups such as free-amines, chloro, are all tolerated under the employed reaction conditions.
- Lai, Chih-Shin,Kao, Hsin-Lun,Wang, Yan-Jhang,Lee, Chin-Fa
-
supporting information; experimental part
p. 4365 - 4367
(2012/09/22)
-
- Oxidoreductive coupling of thiols with aryl halides catalyzed by copper on iron
-
Synthesis and utilization of a simple copper on iron catalyst in the coupling of aryl halides with thiols through disulfide intermediate is reported. The iron support of copper catalyst ensures reductive media for the coupling, allows easy removal of the metals by outer magnetic field and enables the recycling of the catalyst.
- Kovacs, Szabolcs,Novak, Zoltan
-
experimental part
p. 711 - 716
(2011/03/22)
-
- FeF3/i2-catalyzed synthesis of 4-chalcogen- substituted arylamines by direct thiolation of an arene C-H bond
-
An efficient regioselective synthesis of 4-chalcogen-substituted-arylamines by FeF3-catalyzed sulfenylation and selenation of arylamines has been developed. In the presence of FeF3and I2, a variety of arylamines underwent the reaction with disulfides or diselenides to afford the corresponding 4-sulfenyl-or 4-selenenyl-arylamines in moderate to good yields. Georg Thieme Verlag Stuttgart.
- Fang, Xiao-Li,Tang, Ri-Yuan,Zhang, Xing-Guo,Li, Jin-Heng
-
experimental part
p. 1099 - 1105
(2011/05/14)
-
- Carbon-sulfur coupling reactions catalyzed by Pd-NHC complex
-
The cross-coupling reaction of aryl halides with aliphatic or aromatic thiols catalyzed by (SIPr)Pd(Py)Clis reported. This Pd-N-heterocyclic carbene (NHC) complex shows good to excellent activities toward various deactivated electron-rich aryl halides and even with unactivated aryl chlorides in C-S coupling reactions. The reactions proceeded in good yields, broad scope, and high tolerance of functional groups. The Pd-NHC complex is stable and easily to synthesize, so it is an excellent candidate to replace Pd-organophosphanes commonly used in C-S coupling catalysis. Georg Thieme Verlag Stuttgart - New York.
- Shi, Yanhui,Cai, Zhengyuan,Guan, Pei,Pang, Guangsheng
-
supporting information; experimental part
p. 2090 - 2096
(2011/10/09)
-
- Ligand-free palladium-catalyzed C-S coupling reactions using water as solvent and microwaves
-
Herein we demonstrate for the first time a rapid and efficient method for the synthesis of aryl sulfides by the direct substitution reaction of aromatic thiols with aryl halides using water as solvent under microwave irradiation. This procedure offers a high yield in shorter reaction time as compared to conventional methods.
- Velmathi, Sivan,Vijayaraghavan, Reena,Amarendar, Ch.,Pal, Ravindra P.,Vinu, Ajayan
-
experimental part
p. 2733 - 2736
(2010/12/25)
-
- Efficient ligand-free copper-catalyzed C-S cross-coupling of thiols with aryl iodides using KF/Al2O3 as base
-
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
-
experimental part
p. 2489 - 2492
(2010/06/14)
-
- A highly efficient, ligand-free, and recyclable Cu2S-catalyzed coupling of aryl iodides with diaryl disulfides
-
A highly efficient and ligand-free copper(I) sulfide catalyzed cross-coupling reaction of aryl iodides with diaryl disulfides was developed. With only 1 mol-% of Cu2S as the catalyst, iron powder as the reductant, and K2CO3 as the base, aryl iodides reacted with disulfides in DMSO at 90-110 °C for 18-24 h under an atmosphere of argon to give the corresponding aryl sulfides in good to excellent yields. In addition, the catalyst is recyclable and reusable with some loss of activity.
- Wang, Huifeng,Jiang, Linlin,Chen, Tao,Li, Yarning
-
experimental part
p. 2324 - 2329
(2010/07/10)
-
- One-pot synthesis of amine-substituted aryl sulfides and benzo[ b ]thiophene derivatives
-
A series of amine-substituted aryl sulfides have been synthesized from nitroaryl halides via a simple one-pot procedure involving metal-free C-S cross-coupling and in situ nitro group reduction. Various nitroaryl halides were reacted with thiols in recyclable poly(ethylene glycol) to afford the amine-substituted aryl sulfides in high yield. Additionally, the cross-coupling reactions of nitro- and aldehyde-substituted aryl halides with benzyl thiols under the same reaction conditions were demonstrated to afford benzothiazole and phenylbenzo[b]thiophene derivatives.
- Duan, Zhongyu,Ranjit, Sadananda,Liu, Xiaogang
-
supporting information; experimental part
p. 2430 - 2433
(2010/07/10)
-
- Efficient copper-catalyzed S-arylation of thiols with aryl bromides and chlorides
-
An efficient copper-catalyzed system for C-S cross-coupling of aromatic thiols with aryl bromides and chlorides has been developed using 1,2,3,4-tetrahydroquinoline-8-ol as a ligand. It is noteworthy that this method is proved to be especially effective for aryl bromides with electron-donating groups. By this protocol, a variety of thioethers as well as symmetrical and unsymmetrical bis-thioethers are obtained in excellent yields with an exceptional level of functional group tolerance and high chemoselectivity. Georg Thieme Verlag Stuttgart - New York.
- Li, Yaming,Li, Xiaoying,Wang, Huifeng,Chen, Tao,Xie, Yusheng
-
supporting information; experimental part
p. 3602 - 3608
(2010/12/19)
-
- Indium-catalyzed C-S cross-coupling of aryl halides with thiols
-
Indium-catalyzed C-S cross-coupling of aromatic and alkane thiols with aryl halides proceeds smoothly in the presence of In(OTf)3 (10 mol %), TMEDA (20 mol %), and KOH as a base in DMSO at 135 °C. When this protocol was utilized, a variety of thiols could be cross-coupled with aryl halides to afford the corresponding aryl sulfides in good to excellent yields.
- Reddy, V. Prakash,Swapna,Kumar, A. Vijay,Rao, K. Rama
-
supporting information; experimental part
p. 3189 - 3191
(2009/08/08)
-
- A highly efficient and widely functional-group-tolerant catalyst system for copper(I)-catalyzed S-arylation of thiols with aryl halides
-
A mild, general, and efficient copper-catalyzed system for C-S bond formation with high chemoselectivity and wide functional group tolerance is developed. With CuBr as catalyst and 1,2,3,4-tetrahydro-8-hydroxy-quinoline as ligand, the S-arylation of thiols with aryl halides performed well, the activated aryl iodides could take place even at room temperature, and the activated aryl bromides and chlorides give the corresponding products with good to excellent yields as well.
- Feng, Yang,Wang, Huifeng,Sun, Fangfang,Li, Yaming,Fu, Xinmei,Jin, Kun
-
supporting information; experimental part
p. 9737 - 9741
(2010/02/27)
-
- Efficient C-S cross coupling catalyzed by Cu2O
-
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
-
experimental part
p. 434 - 437
(2009/05/11)
-
- Ligand-free C-S bond formation catalyzed by copper(I) oxide
-
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
-
experimental part
p. 3063 - 3067
(2009/07/04)
-
- L-proline-promoted CuI-catalyzed C-S bond formation between aryl iodides and thiols
-
An improved, mild procedure for the CuI-catalyzed coupling reactions of aryl iodides with aliphatic and aromatic thiols, using L-proline as the ligand, is reported. This procedure is noteworthy given its high generality and exceptional level of functional group toleration. Copyright Taylor & Francis Group, LLC.
- Zhang, Hui,Cao, Weiguo,Ma, Dawei
-
-
- Simple and efficient recyclable catalytic system for performing copper-catalysed S-arylation reactions in the presence of water
-
A novel protocol for the copper-catalysed S-arylation of thiophenol derivatives with aryl halides leading to diaryl sulfides is reported. The reactions were catalysed by a combination of a copper salt and a 1,2-diamine derivative (acting both as the ligand and as the base) using exclusively water as the solvent. The recovery and successful reutilisation of the aqueous medium containing the active catalyst is described. Furthermore, one example of a "one-pot" process involving Br/I exchange of an aryl bromide and further S-arylation is presented.
- Carril, Monica,SanMartin, Raul,Dominguez, Esther,Tellitu, Imanol
-
p. 5100 - 5105
(2008/02/09)
-
- Microwave-assisted simple and efficient ligand free copper nanoparticle catalyzed aryl-sulfur bond formation
-
A new protocol for the coupling of aryl iodides with thiophenols and alkanethiols catalyzed by copper nanoparticles under ligand-free condition has been developed. A variety of functionalized aryl sulfides are prepared in excellent yields under microwave irradiation for 5-7 min. A plausible radical mechanism has been suggested.
- Ranu, Brindaban C.,Saha, Amit,Jana, Ranjan
-
p. 2690 - 2696
(2008/09/19)
-
- Convenient synthesis of unsymmetrical organochalcogenides using organoboronic acids with dichalcogenides via cleavage of the S-S, Se-Se, or Te-Te bond by a copper catalyst
-
(Chemical Equation Presented) This article describes the methodology for a copper-catalyzed preparation of numerous monochalcogenides from dichalcogenides with organoboronic acids. Unsymmetrical diorgano-monosulfides, selenides, and tellurides can be synthesized by the coupling of dichalcogenides with aryl- or alkylboronic acids using a copper catalyst in air. The present reaction can take advantage of both organochalcogenide groups on dichalcogenide.
- Taniguchi, Nobukazu
-
p. 1241 - 1245
(2007/10/03)
-