22865-55-0Relevant academic research and scientific papers
Paired Electrolysis Enabled Ni-Catalyzed Unconventional Cascade Reductive Thiolation Using Sulfinates
Kang, Jun-Chen,Li, Zi-Hao,Chen, Chao,Dong, Li-Kun,Zhang, Shu-Yu
supporting information, p. 15326 - 15334 (2021/10/25)
Herein, we have reported a nickel-catalyzed cascade reductive thiolation of aryl halides with sulfinates driven by paired electrolysis. This protocol uses sulfinates as the sulfur source, and various thioethers could be synthesized under mild conditions. By mechanism exploration, we find that a cascade chemical step is allowed on the electrode interface and could alter the reaction pathway in paired electrolysis, whose findings could help the discovery of novel cascade reactions with unique reactivity.
Nickel-Catalyzed Decarbonylative Thioetherification of Acyl Fluorides via C-F Bond Activation
You, Jingwen,Chen, Qiang,Nishihara, Yasushi
supporting information, p. 3045 - 3050 (2021/05/31)
Nickel-catalyzed decarbonylative thioetherification of acyl fluorides has been developed. This transformation allows an array of acyl fluorides to react with thiophenols. A wide range of functional groups are well tolerated and the corresponding sulfides can be obtained in good to excellent yields. This protocol provides the formation of diverse carbon-sulfur bonds via a highly efficient decarbonylative process.
Scalable electrochemical reduction of sulfoxides to sulfides
Kong, Zhenshuo,Pan, Chao,Li, Ming,Wen, Lirong,Guo, Weisi
supporting information, p. 2773 - 2777 (2021/04/21)
A scalable reduction of sulfoxides to sulfides in a sustainable way remains an unmet challenge. This report discloses an electrochemical reduction of sulfoxides on a large scale (>10 g) under mild reaction conditions. Sulfoxides are activated using a substoichiometric amount of the Lewis acid AlCl3, which could be regeneratedviaa combination of inexpensive aluminum anode with chloride anion. This deoxygenation process features a broad substrate scope, including acid-labile substrates and drug molecules.
A template free protocol for fabrication of a Ni(ii)-loaded magnetically separable nanoreactor scaffold for confined synthesis of unsymmetrical diaryl sulfides in water
Arora, Gunjan,Gaur, Rashmi,Gupta, Radhika,Rana, Pooja,Sharma, Rakesh Kumar,Yadav, Manavi,Yadav, Priya
, p. 19390 - 19396 (2020/06/04)
In the present report, an environmentally benign magnetically recoverable nickel(ii)-based nanoreactor as a heterogeneous catalyst has been developedviaa template free approach. The catalytic performance of the synthesized catalyst is assessed in the confined oxidative coupling of arenethiols with arylhydrazines to form unsymmetrical diaryl sulfides under aerobic conditions. The salient features of our protocol include oxidant- and ligand-free conditions, use of water as a green solvent, room temperature and formation of nitrogen and water as the only by-products. Moreover, a broad range of functional groups are tolerated well and provide the corresponding diaryl sulfides in moderate to good yields. Moreover, the heterogeneous nature of the catalyst permits facile magnetic recovery and reusability for up to seven runs, making the present protocol highly desirable from industrial and environmental standpoints.
Copper(II)-faciliated synthesis of substituted thioethers and 5-substituted 1H-tetrazoles: Experimental and theoretical studies
Layek, Samaresh,Agrahari, Bhumika,Dey, Shuvankar,Ganguly, Rakesh,Pathak, Devendra D.
, p. 194 - 206 (2019/06/24)
Benzoylhydrazine based Schiff base-ligated two new copper(II) complexes, [Cu(L1)2] (1) and [Cu(L2)2] (2) were synthesized by the reaction of Cu(CH3COO)2·H2O with respective Schiff base ligand 1-[(4-nitrophenyl)ethylidene] benzohydrazide (HL1) or 1-[(4-methoxyphenyl)ethylidene] benzohydrazide (HL2). Both complexes were isolated as greenish solid and fully characterized by elemental analysis, FT-IR, EPR, thermo-gravimetric (TG) analysis and Cyclic Voltammetry. The molecular structures of both complexes have also been determined by single crystal X-ray crystallography, which confirmed the coordination of Schiff base ligands through N, O donor atoms and distorted square planar geometry around the Cu(II) ion. Both complexes were found to be good homogeneous catalysts for the synthesis of a wide range of substituted thioethers and 5-substituted 1H-tetrazoles in 92% and 93% yield, respectively, at a low catalyst loading (0.5 mol%). The bond angles and distances, as discerned from the DFT calculations, commusurated with the experimental findings. The energy difference between the HOMO and the LUMO, calculated from DFT studies, was found to be 5.645 eV and 6.459 eV for complex 1 and complex 2, respectively. These results are in harmony with the observed higher catalytic activity of complex 1.
C-S cross-coupling reaction using novel and green synthesized CuO nanoparticles assisted by Euphorbia maculata extract
Alinezhad, Heshmatollah,Pakzad, Khatereh
, (2019/08/20)
In the present study, biosynthesis of CuO nanoparticles using a rapid, eco-friendly, cost-effective and efficient method has been reported employing aqueous Euphorbia maculata extract as mild, renewable and non-toxic reducing and capping agents without adding any surfactants. The biogenic and green method has some benefits compared to conventional physical and chemical methods. It is simple, cheap and environmentally friendly. The biosynthesized CuO NP displayed a color change pattern (from sky blue to black) on preparation and presented its respective broad peak at 365?nm, which was analyzed by UV–Vis spectroscopy. Using the FT-IR analysis, biomolecules in E. maculata extract which are responsible for bioreduction activity and synthesize of CuO NP, were identified. The XRD, EDX and FESEM results confirmed the successful synthesis of CuO nanoparticles of 18?nm sizes, with spherical and sponge crystal structure. The catalytic activity of biosynthesized CuO NPs was studied in C-S cross-coupling reaction. This method has the advantages of high yields, easy work-up, and simple reusability. The recovered CuO NP can be reused four times without any considerable loss of its catalytic activity.
CoII immobilized on an aminated magnetic metal-organic framework catalyzed C-N and C-S bond forming reactions: A journey for the mild and efficient synthesis of arylamines and arylsulfides
Mohammadinezhad, Arezou,Akhlaghinia, Batool
, p. 15525 - 15538 (2019/10/19)
In this work, we report a simple and versatile method for the modification of a metal-organic framework (NH2-MIL53(Al)) in a step-wise manner. To characterize the synthesized nanostructured catalyst, a variety of spectroscopic and microscopic techniques including FT-IR, XRD, BET, TEM, FE-SEM, EDX, EDX-mapping, TGA, XPS, VSM, ICP-OES and CHN have been employed. Fe3O4@AMCA-MIL53(Al)-NH2-CoII NPs, which benefit from small nanocrystalline size (10-30 nm, according to the XRD and TEM data) in combination with the coexistence of magnetic nanoparticles, a metal-organic framework, and cobalt species, were found to be an excellent environment catalyst to promote the C-N and C-S cross coupling reactions. A wide range of functional substrates including electron-withdrawing and electron-donating aryl halides underwent the coupling reaction with aromatic/heteroaromatic/benzylic and aliphatic amines and sulfides. The results demonstrated that the yields of the target products were good to excellent and the catalyst can be recycled for at least seven recycling runs without a discernible decrease in its catalytic activity. Furthermore, the heterogeneity studies (such as hot filtration and poisoning tests) efficiently confirmed that the as-synthesized nanostructured catalyst is heterogeneous and completely stable under the reaction conditions. We hope that our study inspires more interest in designing novel catalysts based on using low-cost metal ions (such as cobalt) in the field of cross coupling reactions.
MOF nano porous-supported C-S cross coupling through one-pot post-synthetic modification
Alinezhad, Heshmatollah,Ghasemi, Shahram,Cheraghian, Mansoureh
, (2019/08/07)
UIO-66-NH2-Fu?Ni has been synthesized by anchoring a molecular nickel furfural (Fu) complex into a functionalized nanoporous metal-organic framework (MOF) with the amine functional groups, using the one-pot post-synthetic modification. This new
Nickel-Catalyzed Thiolation of Aryl Halides and Heteroaryl Halides through Electrochemistry
Liu, Dong,Ma, Hong-Xing,Fang, Ping,Mei, Tian-Sheng
supporting information, p. 5033 - 5037 (2019/03/13)
Transition-metal-catalyzed coupling reactions are useful tools for synthesizing aryl sulfur compounds. However, conventional transition-metal-catalyzed thiolation of aryl bromides and chlorides typically requires the use of strong base under elevated reaction temperature. Herein, we report the first examples of nickel-catalyzed electrochemical thiolation of aryl bromides and chlorides in the absence of an external base at room temperature using undivided electrochemical cells.
Metal-Free Cercosporin-Photocatalyzed C-S Coupling for the Selective Synthesis of Aryl Sulfides under Mild Conditions
Li, Jia,Bao, Wenhao,Zhang, Yan,Rao, Yijian
supporting information, p. 7175 - 7178 (2019/11/16)
Aryl sulfides are important motifs of bioactive molecules, which are generally synthesized by transition metal-based coupling reactions under harsh conditions. Herein, we developed a new method that visible light along with cercosporin, produced by liquid fermentation and functioned as a cost-effective and environmentally friendly photocatalyst, prompted the selective synthesis of aryl sulfides through C–S coupling of thiols and diazonium salts under mild conditions. Furthermore, this method can also be performed with a great conversion by the direct use of cercosporin-containing fermentation supernatant as catalytic system without organic solvent extraction.
