18434-12-3Relevant articles and documents
Scope, Kinetics, and Mechanism of “On Water” Cu Catalysis in the C–N Cross-Coupling Reactions of Indole Derivatives
Malavade, Vrunda,Patil, Manish,Patil, Mahendra
supporting information, p. 561 - 569 (2020/02/05)
A simple and cost-effective protocol for the C–N cross coupling of indole derivatives with aryl iodides using CuI/phenanthroline catalytic system in aqueous and DME/H2O solvent mixture is described. The reactions were performed in the absence of phase-transfer catalyst, and afforded N-arylated products in moderate to excellent yields under mild reaction conditions. A systematic tuning of reaction conditions using DME as a co-solvent enables to improve product yields of N-arylation reactions. The broad substrate scope, easy performance, and low loading of catalyst as well as ligand render this approach appropriate for large scale processes. The mechanism of “on water” Cu-catalyzed N-arylation reaction is investigated using kinetic and computational studies, which reveal interesting mechanistic aspects of the reaction. A series of kinetic experiments showed significant rate enhancement for “on water” Cu-catalyzed N-arylation over the reaction performed in the organic solvent (DME). Computational studies corroborated “on water” rate acceleration by delineating the role of water in the reaction. The water induces rate acceleration by stabilizing the transition state of oxidative addition through hydrogen bonding interactions, presumably at the oil-water interface, and thus helps to reduce the free energy of activation of oxidative addition of iodobenzene to the Cu complex, which is identified as the rate-limiting step of reaction.
tBuOK-Promoted Cyclization of Imines with Aryl Halides
Li, Ya-Wei,Zheng, Hong-Xing,Yang, Bo,Shan, Xiang-Huan,Qu, Jian-Ping,Kang, Yan-Biao
, p. 4553 - 4556 (2020/06/08)
A transition-metal-free indole synthesis using radical coupling of 2-halotoluenes and imines via the later-stage C-N bond construction was reported for the first time. It includes an aminyl radical generation by C-H cleaving addition of 2-halotoluenes to imines via the carbanion radical relay and an intramolecular coupling of aryl halides with aminyl radicals. One standard condition can be used for all halides including F, Cl, Br, and I. No extra oxidant or transition metal is required.
ORGANIC COMPOUND FOR OPTOELECTRONIC DEVICE AND ORGANIC OPTOELECTRONIC DEVICE AND DISPLAY DEVICE
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Paragraph 0167-0170, (2019/10/22)
The present invention relates to an organic compound for an organic optoelectronic device represented by chemical formula 1, and an organic optoelectronic device and a display device using the same. The details of the chemical formula 1 are as defined in the specification. One embodiment of the present invention provides a compound for an organic optoelectronic device capable of realizing an organic optoelectronic device with high-efficiency and long-life. Another embodiment of the present invention provides an organic optoelectronic device including the compound for the organic optoelectronic device.
CNT-CuO catalyzed C–N bond formation for N-arylation of 2-phenylindoles
Lim, Jeongah,Kim, Ji Dang,Choi, Hyun Chul,Lee, Sunwoo
supporting information, (2019/10/14)
Carbon nanotube–copper oxide (CNT–CuO) nanocomposites were prepared by depositing CuO nanoparticles onto functionalized CNT surfaces. The structure and elemental content of CNT–CuO were characterized using transmission electron microscopy, X-ray diffraction, and Auger electron spectroscopy. The prepared CNT-CuO was subsequently employed as a catalyst for the coupling reaction of 2-phenylindole with aryl iodides to provide the desired N-aryl 2-phenylindoles in good yields.
Palladium-Catalyzed C-N Cross-Coupling of NH-Heteroarenes and Quaternary Ammonium Salts via C-N Bond Cleavage
Chen, Hongyi,Yang, Hongqin,Li, Nutao,Xue, Xinghua,He, Ze,Zeng, Qingle
, p. 1679 - 1685 (2019/08/20)
In this paper, we extend the substrate class of Buchwald-Hartwig amination to quaternary ammonium salts. In the presence of Pd(OAc)2 and t-BuXPhos, the coupling of aryl- or arylmethyltrimethylammonium triflates with NH-heteroarenes via C-N bond cleavage affords the desired N-aryl or N-arylmethyl heteroarenes in moderate to excellent yields.
Transition-Metal-Free Synthesis of 1,2-Disubstituted Indoles
Chesnokov, Gleb A.,Ageshina, Alexandra A.,Topchiy, Maxim A.,Nechaev, Mikhail S.,Asachenko, Andrey F.
, p. 4844 - 4854 (2019/08/01)
Herein, we report a new transition-metal-free robust and cost-effective method for synthesis of 1,2-disubstituted indoles from easily available unactivated (i.e. without EWG, PPh3 or SiR3 groups) tertiary amides. Scope of synthetic applicability of the presented protocol was shown on 23 examples of 1,2-disubstituted indoles with different substitution patterns obtained in good to excellent yields. The reported method turned out to be especially effective for synthesis of N-arylated 2-CF3-indoles. Moreover, this approach can be performed in a one-pot two-step manner directly from commercially available secondary amines. Mechanistic studies showed that acyl transfer might be an important step in the course of the reaction. Viability of the presented approach for benzofurans and benzothiophenes synthesis was also discussed.
Fabrication of an amyloid fibril-palladium nanocomposite: A sustainable catalyst for C-H activation and the electrooxidation of ethanol
Jayarajan, Ramasamy,Kumar, Rakesh,Gupta, Jagriti,Dev, Gayathri,Kadu, Pradeep,Chatterjee, Debdeep,Bahadur, Dhirendra,Maiti, Debabrata,Maji, Samir K.
supporting information, p. 4486 - 4493 (2019/03/06)
Amyloids are highly ordered nanofibrils and their tensile strength is similar to that of steel, which makes them resistant to extreme pH and temperature. Based on this rationale, we demonstrate a facile synthesis of palladium, copper, platinum, gold and silver nanocomposites using α-Synuclein (α-Syn) fibrils as a template. We showed that an α-Syn-fibril-palladium nanoparticles (α-Syn-PdNPs) composite can be used as a heterogeneous catalyst in C-H bond activation and the electrooxidation of ethanol. The study demonstrated α-Syn-PdNPs to be a superior heterogeneous catalyst for the synthesis of pharmaceutically valuable benzofuran, naphthofuran, coumarin and N-arylindole via C-H activation. Further, the electrooxidation of ethanol using α-Syn-PdNPs displayed an electrochemically active surface area of 160.6 m2 g-1, which is much higher than the previously reported values for supported Pd nanocomposites.
Catalytic Access to Indole-Fused Benzosiloles by 2-Fold Electrophilic C-H Silylation with Dihydrosilanes
Omann, Lukas,Oestreich, Martin
supporting information, p. 767 - 776 (2017/04/21)
A protocol for the catalytic synthesis of indole-fused benzosiloles starting from 2-aryl-substituted indoles and dihydrosilanes is reported. Compared to known procedures, this method does not require prefunctionalized starting materials and, hence, allows for a rapid access to those siloles. The net reaction is a 2-fold electrophilic C-H silylation catalyzed by cationic Ru-S complexes. Both reaction steps were separately investigated, and these results eventually led to the development of a two-step procedure. By preparing new Ru-S complexes with different weakly coordinating anions (WCAs), it is also shown that the latter can have a dramatic influence on the outcome of these reactions. Furthermore, the substrate scope of the new method is discussed.
Isocyanide-Induced Activation of Copper Sulfate: Direct Access to Functionalized Heteroarene Sulfonic Esters
Hong, Xiaohu,Tan, Qitao,Liu, Bingxin,Xu, Bin
supporting information, p. 3961 - 3965 (2017/03/27)
A novel and direct approach to alkyl/aryl heteroarene sulfonic esters using copper sulfate as the environmentally benign inorganic sulfonation reagent was first realized with the aid of isocyanide. A variety of heterocycles reacted to afford the corresponding sulfonic esters through C?H functionalization. In this transformation, the otherwise inert copper sulfate was unusually activated by an isocyanide and employed as the source of the sulfonic substituents in an unprecedented fashion. The findings suggest that an appropriate activator may liberate the chemical activities of some relatively inert inorganic salts for organic synthesis.
Borane-catalyzed indole synthesis through intramolecular hydroamination
Tussing, Sebastian,Ohland, Miriam,Wicker, Garrit,Fl?rke, Ulrich,Paradies, Jan
, p. 1539 - 1545 (2017/02/10)
The reaction of 2-alkynyl anilines with catalytic amounts of B(C6F5)3 (5 mol%) resulted in the formation of 2-substituted indoles according to an intramolecular hydroamination in good to excellent yields. Reaction intermediates as well as products were characterized by NMR spectroscopy and by X-ray crystallography. The domino hydroamination/hydrogenation sequence allowed the efficient synthesis of tetrahydroquinoline 8 in good yield.
