1135-14-4Relevant academic research and scientific papers
CsOH·H2O-promoted synthesis of aryl sulfides via direct coupling of aryl halides and thiols
Varala, Ravi,Ramu,Mujahid Alam,Adapa, Srinivas R.
, p. 1614 - 1615 (2004)
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
A facile method for the synthesis of copper modified amine-functionalized mesoporous zirconia and its catalytic evaluation in C-S coupling reaction
Mallick, Sujata,Rana, Surjyakanta,Parida, Kulamani
, p. 9169 - 9175 (2011)
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.
Environmentally Friendly and Recyclable CuCl 2-Mediated C-S Bond Coupling Strategy Using DMEDA as Ligand, Base, and Solvent
Shen, Guodong,Lu, Qichao,Wang, Zeyou,Sun, Weiwei,Zhang, Yalin,Huang, Xianqiang,Sun, Manman,Wang, Zhiming
supporting information, p. 184 - 198 (2021/09/20)
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.
Development and Application of Efficient Ag-based Hydrogenation Catalysts Prepared from Rice Husk Waste
Unglaube, Felix,Kreyenschulte, Carsten Robert,Mejía, Esteban
, p. 2583 - 2591 (2021/04/09)
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.
Efficient hydrogenation catalyst designing via preferential adsorption sites construction towards active copper
Dai, Xingchao,He, Dongcheng,Li, Teng,Shi, Feng,Wang, Hongli,Wang, Tao,Wang, Xinzhi
, p. 397 - 406 (2021/07/21)
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.
A Robust Pd-Catalyzed C-S Cross-Coupling Process Enabled by Ball-Milling
Browne, Duncan L.,Jones, Andrew C.,Nicholson, William I.,Smallman, Harry R.
supporting information, p. 7433 - 7438 (2020/10/09)
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.
Flavin/I2 catalyzed aerobic oxidative C–H sulfenylation of anilines
Jiang, Xinpeng,Shen, Zhifeng,Zheng, Cong,Fang, Liyun,Chen, Keda,Yu, Chuanming
supporting information, (2020/07/24)
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.
TBAI-mediated sulfenylation of arenes with arylsulfonyl hydrazides in DPDME
Jie, Zhang,Jing, He,Ping, Liu,Xuezhen, Li,Yali, Liu,Yueting, Wei
supporting information, (2020/10/13)
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.
Preventing Pd-NHC bond cleavage and switching from nano-scale to molecular catalytic systems: Amines and temperature as catalyst activators
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)
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.
HETEROCYCLIC COMPOUNDS FOR THE TREATMENT OF EPILEPSY
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Paragraph 0135; 0143; 0144, (2020/06/19)
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.
