13865-48-0Relevant articles and documents
2-Sulfoximidoyl acetic acids from multicomponent petasis reactions and their use as building blocks in syntheses of sulfoximine benzodiazepine analogues
Hommelsheim, Renè,Nú?ez Ponce, Heliana Michaela,Truong, Khai-Nghi,Rissanen, Kari,Bolm, Carsten
, p. 3415 - 3420 (2021)
Upon application of a multicomponent Petasis reaction, a broad range of NH-sulfoximines and boronic acids react with glyoxalic acid to afford the corresponding 2-substituted acetic acids with N-bound sulfoximidoyl groups. The protocol features excellent y
Cross C-S coupling reaction catalyzed by copper(i) N-heterocyclic carbene complexes
Huang, Wei-Kai,Chen, Wei-Ting,Hsu, I.-Jui,Han, Chien-Chung,Shyu, Shin-Guang
, p. 4912 - 4920 (2017)
Copper(i) N-heterocyclic carbene has a good activity towards aryl halides and was used as a model complex to study the catalytic cycle of Cu(i) to catalyze the cross C-S coupling reaction because the N-heterocyclic carbene has a strong electron donating property, and ligand dissociation can be avoided. Free radical scavenger cumene does not retard the yield of the reaction indicating that the catalytic reaction goes through a non free radical path. Switching the solvent from toluene to DMF lowered the yield of the reaction. DFT calculation shows that the activation of aryl halide is the rate determining step, and the activation energy is higher for the reaction in DMF than in toluene. A plausible catalytic cycle is proposed with the support of DFT calculation.
Bis(2-pyridyl)diselenoethers as versatile ligands for copper-catalyzed C-S bond formation in glycerol
Cargnelutti, Roberta,Lang, Ernesto S.,Schumacher, Ricardo F.
, p. 5218 - 5222 (2015)
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.
Carbon-sulphur cross coupling reactions catalyzed by nickel-based coordination polymers based on metalloligands
Kumar, Gulshan,Hussain, Firasat,Gupta, Rajeev
, p. 15023 - 15031 (2017)
This work illustrates two Ni2+ based coordination polymers (CPs, 1-Ni and 2-Ni) synthesized using two related Co3+ based metalloligands offering appended arylcarboxylate groups. The crystal structure of 1-Ni displays a porous 3D network having well-defined major and minor pores whereas 2-Ni exhibits a somewhat densely packed structure. Both CPs supported the exchange of coordinated water molecules and the inclusion of iodine within their porous structure whereas binding studies illustrated that the Ni(ii) ion in these CPs can bind thiophenol, a reagent used in the C-S cross coupling reactions. The two CPs functioned as the reusable heterogeneous catalysts for the C-S cross coupling reactions between substituted aromatic halides and thiophenol as well as cyclohexanethiol and ethanethiol.
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.
A Visible-Light-Harvesting Covalent Organic Framework Bearing Single Nickel Sites as a Highly Efficient Sulfur–Carbon Cross-Coupling Dual Catalyst
Chen, Hui,Liu, Wanlu,Laemont, Andreas,Krishnaraj, Chidharth,Feng, Xiao,Rohman, Fadli,Meledina, Maria,Zhang, Qiqi,Van Deun, Rik,Leus, Karen,Van Der Voort, Pascal
supporting information, p. 10820 - 10827 (2021/04/09)
Covalent Organic Frameworks (COFs) have recently emerged as light-harvesting devices, as well as elegant heterogeneous catalysts. The combination of these two properties into a dual catalyst has not yet been explored. We report a new photosensitive triazine-based COF, decorated with single Ni sites to form a dual catalyst. This crystalline and highly porous catalyst shows excellent catalytic performance in the visible-light-driven catalytic sulfur–carbon cross-coupling reaction. Incorporation of single transition metal sites in a photosensitive COF scaffold with two-component synergistic catalyst in organic transformation is demonstrated for the first time.
Preparation of Recyclable and Versatile Porous Poly(aryl thioether)s by Reversible Pd-Catalyzed C–S/C–S Metathesis
Morandi, Bill,Rivero-Crespo, Miguel A.,Toupalas, Georgios
supporting information, p. 21331 - 21339 (2021/12/17)
Porous organic materials (polymers and COFs) have shown a number of promising properties; however, the lability of their linkages often limits their robustness and can hamper downstream industrial application. Inspired by the outstanding chemical, mechanical, and thermal resistance of the 1D polymer poly(phenylene sulfide) (PPS), we have designed a new family of porous poly(aryl thioether)s, synthesized via a mild Pd-catalyzed C–S/C–S metathesis-based method, that merges the attractive features common to porous polymers and PPS in a single material. In addition, the method is highly modular, allowing to easily introduce application-oriented functionalities in the materials for a series of environmentally relevant applications including metal capture, metal sensing, and heterogeneous catalysis. Moreover, despite their extreme chemical resistance, the polymers can be easily recycled to recover the original monomers, offering an attractive perspective for their sustainable use. In a broader context, these results clearly demonstrate the untapped potential of emerging single-bond metathesis reactions in the preparation of new, recyclable materials.
Palladium complex containing meta-position carborane triazole ligand and preparation method and application of palladium complex
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Paragraph 0041-0043, (2020/08/07)
The invention relates to a palladium complex containing a meta-position carborane triazole ligand and a preparation method and application of the palladium complex. The palladium complex is prepared by the following steps: (1) dropwise adding an n-BuLi solution into a meta-position carborane m-C2B10H12 solution, carrying out stirring and reacting, then adding 3-propargyl bromide for a reaction again, and after the reaction is finished, carrying out separating to obtain 1,3-dipropargyl meta-carborane; and (2) under the catalytic condition of a catalyst CuI, carrying out a reaction on 1,3-dipropargyl meta-carborane and aryl azide, then adding PdCl2 into a reaction system, continuing the reaction, and after the reaction is finished, carrying out separation to obtain the palladium complex containing the meta-carborane triazole ligand. Compared with the prior art, the preparation method provided by the invention is simple and green; the complex can efficiently catalyze a coupling reaction of mercaptan and halogenated hydrocarbon to synthesize thioether compounds; reaction conditions are mild, substrate universality is good, catalytic efficiency is high, and few byproducts are produced;and the catalyst has high stability and is not sensitive to air and water.
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.
DABCO-promoted Diaryl Thioether Formation by Metal-catalyzed Coupling of Sodium Sulfinates and Aryl Iodides
Liu, Yanpeng,Lam, Long Yin,Ye, Jiqing,Blanchard, Nicolas,Ma, Cong
supporting information, p. 2326 - 2331 (2020/05/05)
A scalable catalytic synthesis method using commodity chemicals for constructing diaryl thioethers directly from sodium arylsulfinates and iodoarenes is reported in this study. In the presence of CuO or other copper salts such as Cu(OAc)2 as well as palladium catalysts, DABCO demonstrated to be essential to promote this transformation. Various iodoarenes and aryl sulfinates were examined and demonstrated the viability of this method. The mechanistic study showed that radical reactions occurred, while DABCO N-oxide radical can be observed by mass spectrometry. A plausible catalytic mechanism involving DABCO is also discussed, suggesting synergistic reduction of sulfinate by Cu(II) and DABCO is the key step of this coupling reaction. (Figure presented.).
