404-38-6Relevant academic research and scientific papers
Palladium-catalysed thioetherification of aryl and alkenyl iodides using 1,3,5-trithiane as sulfur source
Kollár, László,Rajat Rao, Yalamarti Venkat,Zugó, Alexandra,Pongrácz, Péter
, (2021/12/17)
Thioetherification reaction of aryl iodides catalysed by palladium(II) complexes in the presence of 1,3,5-trithiane as sulphur source is reported. The paper presents the first homogeneous catalytic application of 1,3,5-trithiane in synthesis. Detailed optimization steps, the frames of the novel reaction are described, as well as the limitations and the substrate scope are also demonstrated. Moderate to good thioether yields were achieved in the presence of various substituted iodobenzenes and some alkenyl iodides, using palladium-xantphos catalyst system. Competitive reactions in the presence of mixed substrates were also performed and mechanistic considerations were assumed.
Heterogeneously Ni-Pd nanoparticle-catalyzed base-free formal C-S bond metathesis of thiols
Mitamura, Kanju,Yatabe, Takafumi,Yamamoto, Kidai,Yabe, Tomohiro,Suzuki, Kosuke,Yamaguchi, Kazuya
supporting information, p. 3749 - 3752 (2021/04/21)
This study rationally designed a heterogeneously catalyzed system (i.e., using Ni-Pd alloy nanoparticles supported on hydroxyapatite (Ni-Pd/HAP) under an H2atmosphere) achieving an efficient base-free formal C-S bond metathesis of various thiolsviasuppression of the Ni catalysis deactivation.
Organic long-afterglow compound, and preparation method and application thereof
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Paragraph 0066-0070, (2020/02/14)
The invention discloses an organic long-afterglow compound, and a preparation method and application thereof, and belongs to the technical field of photodynamic therapy. According to the invention, the long-afterglow compound with a brand-new structure is designed and synthesized on the basis of oxygen group elements. The long-afterglow compound has the following advantages: 1, the imaging time islong, and nanosecond-grade imaging of traditional fluorescent imaging agents is improved to millisecond-imaging of the organic long-afterglow material; 2, the oxygen group elements are introduced into the long-afterglow compound, so that the yield of triplet excitons of molecules is introduced, and generation of reactive oxygen is promoted; 3, the excitation range of the long-afterglow compound can be extended to visible light, and the long-afterglow compound can easily achieve a good therapeutic effect under visible light irradiation and has low biological toxicity; and 4, the long-afterglowcompound has good biocompatibility. According to the invention, experiments prove that the compound has obvious inhibitory activity on Gram-positive bacteria, and thus the compound has a potential for being used as a photosensitizer for effective photodynamic therapy.
Dechalcogenization of Aryl Dichalcogenides to Synthesize Aryl Chalcogenides via Copper Catalysis
Cao, Fei,Chen, Jinhong,Deng, Jiedan,Deng, Xuemei,Hou, Yongsheng,Shao, Xiangfeng,Shi, Tao,Wang, Yongqiang,Wang, Zhen,Wu, Lingxi,Yang, Jinru,Yang, Yuhang
, p. 2707 - 2712 (2020/03/11)
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.
Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides
Li, Xing,Du, Jia,Zhang, Yongli,Chang, Honghong,Gao, Wenchao,Wei, Wenlong
, p. 3048 - 3055 (2019/03/21)
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.
Copper-Catalyzed Production of Diaryl Sulfides Using Aryl Iodides and a Disilathiane
Ogiwara, Yohei,Maeda, Hiromu,Sakai, Norio
supporting information, p. 655 - 657 (2017/11/29)
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.
Iron-catalyzed carbon–sulfur bond formation: Atom-economic construction of thioethers with diaryliodonium salts
Liu, Li,Qiang, Jian,Bai, Shuhua,Li, Yang,Li, Jian
, p. 2365 - 2371 (2017/09/30)
Diaryliodonium salts are characterized by poor atom economy with the formation of one equivalent of an iodoarene as waste. We have developed an atom-economic iron-catalyzed protocol for the synthesis of a variety of thioethers with diaryliodonium salts. Not only cyclic diaryliodonium salts but also linear diaryliodonium salts were found to perform well in the reactions.
A simple and green synthesis of diaryl sulfides catalyzed by an MCM-41-immobilized copper(I) complex in neat water
Cai, Mingzhong,Xiao, Ruian,Yan, Tao,Zhao, Hong
, p. 55 - 60 (2013/10/22)
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.
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
Chen, Hsing-Ying,Peng, Wei-Te,Lee, Ying-Hsien,Chang, Yu-Lun,Chen, Yen-Jen,Lai, Yi-Chun,Jheng, Nai-Yuan,Chen, Hsuan-Ying
supporting information, p. 5514 - 5522 (2013/11/06)
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.
