53279-52-0Relevant academic research and scientific papers
Synthesis of diaryl sulfides based on copper-doped OMS-2
Yu, Shao-Qiang,Liu, Na,Liu, Ming-Guo,Wang, Long
, p. 237 - 241 (2020/11/30)
We describe a practical protocol for efficiently preparing diaryl sulfide compounds using Cu–OMS-2 as the catalyst. Cu–OMS-2 originates from manganese oxide octahedral molecular sieves modified with copper ions and catalyzes the C–S coupling reaction of substituted thiophenols and aryl halides. This protocol has the advantages of environmental friendliness, simple operation, high yields, good tolerance of functional groups, and the Cu–OMS-2 catalytic material can be recycled several times.
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.
Forging C?S(Se) Bonds by Nickel-catalyzed Decarbonylation of Carboxylic Acid and Cleavage of Aryl Dichalcogenides
Zhou, Jing-Ya,Zhu, Yong-Ming
, p. 2452 - 2461 (2021/06/28)
A nickel-catalyzed decarbonylation of carboxylic acids cross-coupling protocol has been developed for the straightforward C?S(Se) bond formation. This reaction is promoted by a commercially-available, user-friendly, inexpensive, air and moisture-stable nickel precatalyst. Various carboxylic acids and a wide range of aryl dichalcogenide substrates were tolerated in this process which afforded products in good to excellent yields. In addition, the present reaction can be conducted on gram scale in good yield.
Exploration of the mechanism and scope of the CuI/DABCO catalysed C–S coupling reaction
Thomas, Anns Maria,Sherin,Asha, Sujatha,Manojkumar,Anilkumar, Gopinathan
supporting information, (2019/12/26)
A cost effective and easily available CuI/DABCO catalytic system has been developed for the C–S cross-coupling reaction. This method is extremely useful for the thioetherification of aryl and heteroaryl halides, providing excellent yields and good chemoselectivity. We have also explored the mechanism of the reaction using DFT studies.
Microwave-Assisted Copper Slag-Catalyzed Green S-Arylation of Arenethiols with Arylboronic Acids
Gavane, D. S.,Jambhorkar, V. S.,Kale, B. D.,Karnik, K. S.,Khandare, A. L.,Narula, I. S.,Rajhans, A. P.,Sarkate, A. P.
, p. 1300 - 1303 (2020/10/02)
Abstract: Diaryl sulfides have been synthesized in moderate to excellent yield by S-arylation of arenethiols with arylboronic acids using copper slag as a catalyst. Copper slag is a by-product obtained from smelting and refining of copper. Conventional heating method has been compared with the microwave-assisted technique. The proposed microwave-assisted synthesis provides excellent yields of diaryl sulfides in a short time (10 min) and is ligand-free, green, and cost-effective.
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.
Metal-organic layers as multifunctional two-dimensional nanomaterials for enhanced photoredox catalysis
Lan, Guangxu,Quan, Yangjian,Wang, Maolin,Nash, Geoffrey T.,You, Eric,Song, Yang,Veroneau, Samuel S.,Jiang, Xiaomin,Lin, Wenbin
supporting information, p. 15767 - 15772 (2019/10/11)
Metal-organic layers (MOLs) have recently emerged as a novel class of molecular two-dimensional (2D) materials with significant potential for catalytic applications. Herein we report the design of a new multifunctional MOL, Hf12-Ir-Ni, by laterally linking Hf12 secondary building units (SBUs) with photosensitizing Ir(DBB)[dF(CF3)ppy]2+ [DBB-Ir-F, DBB = 4,4′-di(4-benzoato)-2,2′-bipyridine; dF(CF3)ppy = 2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine] bridging ligands and vertically terminating the SBUs with catalytic Ni(MBA)Cl2 [MBA = 2-(4′-methyl-[2,2′-bipyridin]-4-yl)acetate] capping agents. Hf12-Ir-Ni was synthesized in a bottom-up approach and characterized by TEM, AFM, PXRD, TGA, NMR, ICP-MS, UV-vis, and luminescence spectroscopy. The proximity between photosensitizing Ir centers and catalytic Ni centers (～0.85 nm) in Hf12-Ir-Ni facilitates single electron transfer, leading to a 15-fold increase in photoredox reactivity. Hf12-Ir-Ni was highly effective in catalytic C-S, C-O, and C-C cross-coupling reactions with broad substrate scopes and turnover numbers of ～4500, ～1900, and ～450, respectively.
Electrochemically Promoted Nickel-Catalyzed Carbon-Sulfur Bond Formation
Wang, Yang,Deng, Lingling,Wang, Xiaochen,Wu, Zhengguang,Wang, Yi,Pan, Yi
, p. 1630 - 1634 (2019/03/08)
This work describes a nickel-catalyzed Ullmann-type thiolation of aryl iodidesunder mild electrochemical conditions. The simple undivided cell with graphene/nickel foam electrode setups offers excellent substrate tolerance, affording aryl and alkyl sulfides in good chemical yields. Furthermore, the mechanism for this electrochemical cross-coupling reaction has been investigated by cyclic voltammetry.
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.
A semiconducting supramolecular Co(ii)-metallohydrogel: an efficient catalyst for single-pot aryl-S bond formation at room temperature
Dhibar, Subhendu,Dey, Amiya,Jana, Rajkumar,Chatterjee, Arpita,Das, Gourab Kanti,Ray, Partha Pratim,Dey, Biswajit
supporting information, p. 17388 - 17394 (2019/12/02)
A novel mechanically stable supramolecular Co(ii)-metallohydrogel has been synthesized. Cobalt(ii) nitrate hexahydrate and monoethanolamine, as a low molecular weight organic gelator, are used to get the gel. The mechanical stability of the supramolecular hydrogel was analyzed. The morphology of the supramolecular metallohydrogel was scrutinized. The semiconducting features of the metallohydrogel were studied. The conducting properties of the Co(ii)-metallohydrogel establish a Schottky barrier diode type nature. The catalytic nature of the Co(ii)-metallohydrogel based room temperature single pot aryl-S coupling reaction was explored. Most interestingly, the Co(ii)-metallohydrogel based catalytic aryl-S coupling reaction does not require any column-chromatographic purification protocol to get pure aryl-thioethers. Thus, through this work a semiconducting Schottky barrier diode application and catalytic role in the room temperature single pot aryl-S coupling reaction of a supramolecular Co(ii)-metallohydrogel have been explored.
