3699-01-2Relevant academic research and scientific papers
Reduction of aryl thiocyanates with SmI2 and Pd-catalyzed coupling with aryl halides as a route to mixed aryl sulfides
Still, Ian W. J.,Toste, F. Dean
, p. 7677 - 7680 (1996)
A series of aryl iodides, with a range of substituents, has been successfully coupled using 10 mol percent Pd catalyst with samarium thiolates, derived from the corresponding aryl thiocyanates upon reductive cleavage with SmI2. Reactions proceed in THF at 65°C in yields ranging from good to excellent and are compatible with both electron-donating and electron-withdrawing substituents, except NO2. The reactions may also be conducted with aryl bromides although with somewhat lower yields.
Interception of benzyne with thioethers: A facile access to sulfur ylides under mild conditions
Xu, Hua-Dong,Cai, Mao-Qiang,He, Wei-Jie,Hu, Wen-Hao,Shen, Mei-Hua
, p. 7623 - 7626 (2014)
Reactive benzyne generated from o-(trimethylsilyl)phenyl triflate under the action of CsF has been trapped in situ by thioethers to give sulfonium ylides, which in turn have been intercepted by isatins to give rise to corresponding spiroepoxy oxindoles in moderate to high yields. This reaction provides a facile and efficient synthesis of spiroepoxy oxindoles.
Palladium Complex Immobilized on Magnetic Nanoparticles Modified with 2-Aminopyridine Ligand: A Novel and Efficient Recoverable Nanocatalyst for C–S and C–Se Coupling Reactions
Lu, Lu,Luo, Jia,Wang, Weiqi,Xu, Xiaoqing,Zhang, Jingzheng
, (2022/01/12)
A novel, versatile and efficient magnetically recoverable palladium nanocatalyst [Fe3O4@SiO2/2-aminopyridine-Pd(II)] was fabricated via the immobilization of palladium(II) complex on the surface of magnetic nanoparticles modified with 2-aminopyridine ligand. The structure of the as-fabricated Fe3O4@SiO2/2-aminopyridine-Pd(II) nanocomposite was characterized by a series of spectroscopic techniques including FT-IR, SEM, TEM, EDX, TGA, XRD, VSM and ICP-OES techniques. The Fe3O4@SiO2/2-aminopyridine-Pd(II) nanocomposite was utilized under mild and eco-friendly conditions in C–S and C–Se coupling reactions to afford a vast variety of diaryl sulfides and diaryl selenides with good to excellent yields. This heterogeneous palladium catalyst can be magnetically separated and reused for at least 7 consecutive trials without any reduction in activity. Graphical Abstract: [Figure not available: see fulltext.]
Dimsyl Anion Enables Visible-Light-Promoted Charge Transfer in Cross-Coupling Reactions of Aryl Halides
Pan, Lei,Cooke, Maria Victoria,Spencer, Amara,Laulhé, Sébastien
supporting information, p. 420 - 425 (2021/11/01)
A methodology is reported for visible-light-promoted synthesis of unsymmetrical chalcogenides enabled by dimsyl anion in the absence of transition-metals or photoredox catalysts. The cross-coupling reaction between aryl halides and diaryl dichalcogenides proceeds with electron-rich, electron-poor, and heteroaromatic moieties. Mechanistic investigations using UV-Vis spectroscopy, time-dependent density functional theory (TD-DFT) calculations, and control reactions suggest that dimsyl anion forms an electron-donor-acceptor (EDA) complex capable of absorbing blue light, leading to a charge transfer responsible for generation of aryl radicals from aryl halides. This previously unreported mechanistic pathway may be applied to other light-induced transformations performed in DMSO in the presence of bases and aryl halides.
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.
Site-Selective Synthesis of Aryl Sulfides via Oxidative Aromatization of Cyclohexanones with Thiophenols
Xiao, Fuhong,Tang, Minli,Huang, Huawen,Deng, Guo-Jun
, p. 512 - 523 (2021/12/27)
We have introduced a metal-free facile access for the thiolation/aromatization of cyclohexanones with thiophenols to the corresponding aryl sulfides. The dehydroaromatic reaction of non-aromatic cyclohexanones proceeded smoothly using oxygen as a green oxidant.
Electrochemistry Enabled Nickel-Catalyzed Selective C?S Bond Coupling Reaction
Pan, Yi,Wang, Yang,Wang, Yi,Zhang, Feng
supporting information, (2022/02/16)
This work describes an electrochemical enabled nickel-catalyzed chemoselective C?S bond coupling protocol for the production of aryl sulfides and sulfones. By simply switching the nickel catalysts and electrodes, this electrochemical C?S bond coupling has demonstrated excellent redox activity, scalability and sustainability. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated.
Deoxygenative C-S Bond Coupling with Sulfinates via Nickel/Photoredox Dual Catalysis
Deng, Guo-Jun,Huang, Huawen,Mao, Guojiang,Zhao, Feng,Zhong, Shuai,Zhou, Zhiwei
supporting information, p. 1865 - 1870 (2022/03/16)
The C-S bond formation from aryl halides and thiols has been well established under various catalytic systems. In this work, user-friendly sulfinates have been exploited as an efficient sulfenylating reagent in the C-S couplings through visible-light-induced photo/nickel dual catalysis under base- and external reductant-free conditions. A large number of aryl sulfide products were accessed with high selectivity and high tolerance of various functionalities.
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
, 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.
Rh(I)-Catalyzed Intramolecular Decarbonylation of Thioesters
Cao, Han,Liu, Xuejing,Bie, Fusheng,Shi, Yijun,Han, Ying,Yan, Peng,Szostak, Michal,Liu, Chengwei
, p. 10829 - 10837 (2021/07/28)
Decarbonylative synthesis of thioethers from thioesters proceeds in the presence of a catalytic amount of [Rh(cod)Cl]2 (2 mol %). The protocol represents the first Rh-catalyzed decarbonylative thioetherification of thioesters to yield valuable thioethers. Notable features include the absence of phosphine ligands, inorganic bases, and other additives and excellent group tolerance to aryl chlorides and bromides that are problematic using other metals to promote decarbonylation. Gram scale synthesis, late-stage pharmaceutical derivatization, and orthogonal site-selective cross-couplings by C-S/C-Br cleavage are reported.
