3169-69-5Relevant academic research and scientific papers
Method for synthesizing asymmetric sulfide from molecular oxygen oxidation water phase under catalysis of water-soluble transition metal compound
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Paragraph 0061-0064, (2019/07/29)
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.
Surfactant-Type Catalyst for Aerobic Oxidative Coupling of Hydrazine with Thiol in Water
Ren, Xuanhe,Tang, Shanyu,Li, Longjia,Li, Jiao,Liang, Helong,Li, Ganzhong,Yang, Guanyu,Li, Heng,Yuan, Bingxin
, p. 8683 - 8690 (2019/07/08)
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.
Aerobic copper-catalyzed decarboxylative thiolation
Li, Minghao,Hoover, Jessica M.
supporting information, p. 8733 - 8736 (2016/07/15)
Copper-catalyzed decarboxylative thiolation using molecular oxygen as the sole oxidant was developed. A variety of aromatic carboxylic acids including 2-nitrobenzoic acids, pentafluorobenzoic acid and several heteroaromatic carboxylic acids undergo efficient thiolation to furnish the aryl sulfides in moderate to excellent yields.
Bis(2-pyridyl)diselenoethers as versatile ligands for copper-catalyzed C-S bond formation in glycerol
Cargnelutti, Roberta,Lang, Ernesto S.,Schumacher, Ricardo F.
supporting information, p. 5218 - 5222 (2015/08/19)
In this Letter, we describe a simple and efficient general methodology for CuI/bis(2-pyridyl)diselenoether-catalyzed C-S coupling reactions of aryl halides with thiols using glycerol as an environmentally friendly solvent. The products were obtained in moderate to excellent yields. The performance of CuI/L3-catalyzed C-S coupling reactions in glycerol is comparable to the related cross-coupling reactions in common organic solvents using transition-metal salts as catalyst. The use of the system CuI/L3/glycerol related in this work offers the possibility of performing the reaction in the absence of toxic organic solvents, expensive metals and using ultrasound as an alternative energy source.
Synthesis and biological evaluation of optimized inhibitors of the mitotic kinesin Kif18A
Braun, Joachim,M?ckel, Martin M.,Strittmatter, Tobias,Marx, Andreas,Groth, Ulrich,Mayer, Thomas U.
, p. 554 - 560 (2015/04/21)
The mitotic spindle, a highly dynamic structure composed of microtubules, mediates the segregation of the previously duplicated genome into the two nascent daughter cells. Errors in this process contribute to pathology including tumor formation. Key for the shape and function of the mitotic spindle are kinesins, molecular motor proteins that convert chemical energy into mechanical work. Due to their fast mode of action, small molecules are valuable tools to dissect the dynamic functions of kinesins during mitosis. In this study, we report the identification of optimized small molecule inhibitors of the mitotic kinesin Kif18A. Using BTB-1, the first identified Kif18A inhibitor, as a lead compound, we synthesized a collection of derivatives. We demonstrate that some of the synthesized derivatives potently inhibited the ATPase activity of Kif18A with a half maximal inhibitory concentration (IC50) value in the low micromolar range. In vitro analysis of a panel of Kif18A-related kinesins revealed that the two most potent compounds show improved selectivity compared to BTB-1. Structure-activity relationship studies identified substituents mediating undesired inhibitory effects on microtubule polymerization. In summary, our study provides key insights into the mechanism of action of BTB-1 and its analogs, which will have a great impact on the further development of highly selective and bioactive Kif18A inhibitors. Since Kif18A is frequently overexpressed in solid tumors, such compounds are not only of great interest for basic research but also have the potential to open up new strategies for the treatment of human diseases.
Iridium and phosphine promoted C-F bond activation: The C-S cross-coupling of aryl fluorides with diaryl disulfides to synthesize thioethers
Li, Liang,Miao, Hongyan,Ding, Yuqiang
supporting information, p. 6405 - 6408 (2015/11/16)
Carbon-fluorine bond is the strongest known single bond to carbon and proved very difficult to cleave. An iridium and phosphine promoted C-F bond activation was developed, for the first time achieving the C-S cross-coupling reaction of disulfides with aryl fluorides using iridium complex. The corresponding monoarylthiolation products were obtained at moderate to good yields. Thus, it represents a new method for the synthesis of aryl sulfides through C-F bond activation.
Potassium tert-butoxide-mediated synthesis of unsymmetrical diaryl ethers, sulfides and selenides from aryl bromides
Kumar, Amit,Bhakuni, Bhagat Singh,Prasad, Ch. Durga,Kumar, Shailesh,Kumar, Sangit
, p. 5383 - 5392 (2013/07/04)
Potassium tert-butoxide mediated carbon-chalcogen C-E (E=O, S and Se) coupling reaction has been studied from aryl bromide and phenol/aryl disulfide/diselenide substrates. A series of unsymmetrical diaryl chalcogenides were accessed from aryl bromide and diaryl dichalcogenide precursors by using 2.5 equiv of potassium tert-butoxide in DMSO at 80 C. Unsymmetrical diaryl ethers were also obtained by using phenol precursors at 40-45 C. Aryl bromides with methyl, trifluoromethyl, methoxy and nitro substituents showed compatibility in the carbon-chalcogen bond forming reaction. 4-Methoxy, methyl, trifluoromethyl substituted bromobenzene substrates gave two regioisomers: 3-substituted and 4-substituted diaryl chalcogenides when reacted with phenols/diaryl disulfides/diselenides. Formation of two regioisomeric diaryl chalcogenides in the reaction mixture suggests that potassium tert-butoxide reacts with bromobenzene to produce benzyne intermediate, which subsequently reacts with diaryl dichalcogenides and finally give a regioisomeric mixture of 4-substituted and 3-substituted diaryl chalcogenides.
KF/clinoptilolite: An efficient promoter for the synthesis of thioethers
Salmanpour, Sadegh,Khalilzadeh, Mohammad A.,Hosseini, Abolfazl
, p. 339 - 344 (2013/07/28)
Potassium fluoride impregnated on natural zeolite as a new solid base system effectively catalyzes the coupling of thiophenols with electron-deficient fluoro-, chloro- and bromo-arenes in DMSO. This versatile and efficient solid base has been demonstrated to afford the corresponding desired products in good to excellent yields. This procedure provides a convenient, efficient and practical method for the preparation of diaryl thioethers.
Microwave-assisted cross-coupling for the construction of diaryl sulfides
Tan, Chen-Ming,Chen, Grace Shiahuy,Chena, Chien-Shu,Chern, Ji-Wang
experimental part, p. 94 - 100 (2011/11/06)
The construction of diaryl sulfides through the cross-coupling of aryl iodides and thiols in microwave heating is described. By using this method, a variety of diaryl sulfides can be prepared in a mild condition and in high yields. Deactivated 4-nitrothiophenol was effective to afford the product in 94% yield. Sterically hindered ortho-substituted aryl iodides or thiophenols provided diaryl sulfides effectively by this microwave-assisted coupling reaction.
Synthesis of aryl sulfides by decarboxylative C-S cross-couplings
Duan, Zhongyu,Ranjit, Sadananda,Zhang, Pengfei,Liu, Xiaogang
supporting information; experimental part, p. 3666 - 3669 (2009/12/07)
A study was conducted to demonstrate the transition-metal-catalyzed synthesis of aryl sulfides by decarboxylative C-S cross-couplings. Coupling reaction of 2-nitrobenzoic acid with 1-octanethiol were carried in the presence of different combinations of tr
