- Copper pyrithione (CuPT)-catalyzed/mediated amination and thioarylation of (hetero)aryl halides: A competition
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A facile method for the synthesis of N-arylheterocycles and di(hetero)aryl sulfides under mild condition is described. In these transformations, copper pyrithione (CuPT) was used as the copper catalyst for C─N coupling, while served as catalyst and coupled partner for C─S coupling with high yields and broad substrate tolerance. The S-arylation process was also utilized for the construction of valuable bioactive 2-sulfonylpyridine 1-oxide derivatives.
- Cao, Ningtao,Song, Bao,Xie, Jianwei,Zhang, Jie
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- ORGANOMETALLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
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An organic light-emitting device is provided to include: a first electrode; a second electrode facing the first electrode; an organic layer between the first electrode and the second electrode, the organic layer including an emission layer; and at least o
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Paragraph 0441; 0443
(2020/07/23)
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- α-d-Galacturonic Acid as Natural Ligand for Selective Copper-Catalyzed N-Arylation of N-Containing Heterocycles
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The first application of α-d-galacturonic acid hydrate (GalA) is reported here, as a potential O-donor ligand. The C-N couplings of N-heterocycles with aryl halides or arylboronic acids could be readily conducted and exhibited good functional group tolerance with characters of selectivity. These N-Arylazoles allow rapid access to several pharmaceutical intermediates and can be easily transformed into a variety of other interesting scaffolds as well.
- Yuan, Chunling,Zhao, Yingdai,Zheng, Li
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p. 2173 - 2180
(2019/11/25)
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- Bivalent platinum complex, preparation method therefor and application of bivalent platinum complex
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The invention belongs to the technical field of organic electroluminescent materials and provides a bivalent platinum complex, an application thereof and an organic light emitting diode (OLED) device.The bivalent platinum complex provided by the invention
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Paragraph 0112; 0113; 0114; 0115
(2019/12/25)
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- SPIRO-CONTAINING PLATINUM (II) EMITTERS WITH TUNABLE EMISSION ENERGIES AND SYNTHESES THEREOF
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An asymmetric tetradentate metal complex of a N^C^C^N comprising tetradentate ligand has a metal connected to binding sites which are connected to each other via three or four covalent bonds that can be either single or double bonds with bridging linkers reside between C^C and C^N moieties. These linkers result in three-dimension metal complexes with distorted square planar geometries. The four donor atoms coordinate to a metal center. Upon metal binding a 5-6-6 membered metallocycle is formed upon chelation including a first nitrogen donor bond, a first metal-carbon bond, a second metal-carbon bond, and a second nitrogen donor bond. The light emission from these metal complexes can be tuned by the ligand structure over the entire visible spectrum.
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Page/Page column 19
(2019/08/12)
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- TETRADENTATE AND OCTAHEDRAL METAL COMPLEXES CONTAINING NAPHTHYRIDINOCARBAZOLE AND ITS ANALOGUES
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Tetradentate and octahedral metal complexes suitable for use as phosphorescent or delayed fluorescent and phosphorescent emitters in display and lighting applications.
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Paragraph 0209; 0210
(2016/12/26)
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- Ethylene glycol, an efficient and recoverable medium for copper-catalyzed N-arylation of diazoles under microwave irradiation
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Ethylene glycol was used as an efficient and recoverable medium for the reaction of diazoles with aryl iodides and aryl bromides in the presence of CuCl2 as the catalyst and K2CO3 as the base. Consequently, imidazole, benzimidazole, and pyrazole reacted readily under microwave irradiation to give good to excellent yields of their corresponding N-arylated products in relatively short time periods. Apparently, ethylene glycol plays a dual role by activating the catalyst and also providing a homogenous medium for the processes. The reaction medium consisting of the solvent, the base, and the copper salt was recovered and reused successfully in the next several reactions.
- Sharifi, Ali,Ghonouei, Nima,Abaee, M. Saeed
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supporting information
p. 249 - 256
(2016/03/09)
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- Copper-catalyzed arylation of nitrogen heterocycles from anilines under ligand-free conditions
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The arylation of pyrazole and derivatives can be achieved by coupling arenediazonium species (formed in situ from anilines) by using a catalytic system that employs low-toxicity and inexpensive copper metal under very mild and ligand-free conditions (T = 20 ° C). From other nitrogen heterocycles, the presence of an additive (NBu4I) significantly improves the efficiency of the catalytic system. These results represent the first examples of C-N bond formation from arenediazonium species.
- Toummini, Dounia,Tlili, Anis,Bergs, Julien,Ouazzani, Fouad,Taillefer, Marc
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supporting information
p. 14619 - 14623
(2015/01/09)
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- 3-(Diphenylphosphino)propanoic acid: An efficient ligand for the Cu-catalyzed N-arylation of imidazoles and 1H-pyrazole with aryl halides
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3-(Diphenylphosphino)propanoic acid (L2) has proved to be an efficient ligand for the copper-catalyzed CN coupling reactions. N-arylation of imidazoles with aryl iodides catalyzed by CuCl/L2 was smoothly carried out in DMSO at 100 °C with a yield up to 98%. N-arylation of 1H-pyrazole with aryl iodides and bromides catalyzed by Cu(OAc)2/L2 in 1,4-dioxane also gave the corresponding products with yields of 40%-98%.
- Liu, Ya-Shuai,Liu, Yan,Ma, Xiao-Wei,Liu, Ping,Xie, Jian-Wei,Dai, Bin
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p. 775 - 778
(2014/06/09)
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- Ruthenium-catalyzed C-H functionalization of arylpyrazoles: Regioselective acylation with acid chlorides
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A ruthenium-catalyzed C-H acylation of arylpyrazoles with a variety of acyl chlorides is described. The acylation reaction exhibits good regioselectivity and both aromatic and aliphatic acyl chlorides can be effectively coupled to the arylpyrazoles at the
- Liu, Po Man,Frost, Christopher G.
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supporting information
p. 5862 - 5865
(2013/12/04)
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- Transition-metal-free O-,S -, and N-arylation of alcohols, thiols, amides, amines, and related heterocycles
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A new protocol for the Ullmann-type arylation process of different aromatic heterocycles without any transition-metal catalyst, implying the use of a combination of an excess of potassium hydroxide and dimethyl sulfoxide, is described. The reaction can be performed between a broad range of starting nucleophiles including phenol, alcohols, amines, nitrogen-containing five-membered systems such as pyrazoles, imidazoles, and indoles, and amides with haloarenes, iodide and bromide derivatives giving the best results, the possible pathway involving the in situ generation of the corresponding benzyne intermediate. When the reaction was performed with 2-iodoaniline and either carboxamides or isothiocyanato derivatives, the corresponding benzoazole derivatives were obtained.
- Cano, Rafael,Ramon, Diego J.,Yus, Miguel
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experimental part
p. 654 - 660
(2011/03/20)
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- N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative metallation using a combination of lithium and zinc amides
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A series of N-aryl and N-heteroaryl pyrazoles have been deproto-metallated using a 2,2,6,6-tetramethylpiperidino-based mixed lithium-zinc combination. Mono-, di-, and tri-iodides have been obtained after subsequent trapping with iodine, depending on the s
- Chevallier, Floris,Halauko, Yury S.,Pecceu, Christelle,Nassar, Ibrahim F.,Dam, To Uyen,Roisnel, Thierry,Matulis, Vadim E.,Ivashkevich, Oleg A.,Mongin, Florence
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scheme or table
p. 4671 - 4684
(2011/07/07)
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- A manganese/copper bimetallic catalyst for C-N coupling reactions under mild conditions in water
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An efficient and convenient bimetallic MnF2/CuI catalyst in combination with trans-1,2-diaminocyclohexane has been developed for the cross-coupling of nitrogen heterocycles with aryl halides in water at moderate temperature. A variety of nitrogen nucleophiles including pyrazole, 7-azaindole, indazole, indole, pyrrole and imidazole afforded the corresponding products in moderate to good yields (up to 94%) under the described arylation conditions.
- Teo, Yong-Chua,Yong, Fui-Fong,Lim, Gina Shiyun
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supporting information; experimental part
p. 7171 - 7174
(2012/01/05)
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- Iron complex-catalyzed N-arylation of pyrazoles under aqueous medium
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Commercially available FeCl3·6H2O with conformationally rigid diamine ligand is a highly effective catalyst for N-arylation of pyrazoles using aryl and heteroaryl iodides. It is notable to show that this complex is tolerable under aqueous medium and particularly the whole reaction utilizes water as the sole solvent without any additional organic co-solvents and surfactants. Attempted study using other nitrogen nucleophiles is described. This newly developed system provides an alternative protocol to Cu- and Pd-catalyzed N-arylation reactions.
- Lee, Hang Wai,Chan, Albert S.C.,Kwong, Fuk Yee
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experimental part
p. 5868 - 5871
(2010/01/11)
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- Microwave-assisted solvent-free N-arylation of imidazole and pyrazole
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Solvent-free coupling reactions between imidazole or pyrazole and aryl bromides were achieved with microwave irradiation using copper salts and l-amino acids as catalysts.
- Chow, Wai Shan,Chan, Tak Hang
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scheme or table
p. 1286 - 1289
(2009/09/06)
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- Efficient cross-coupling reactions of nitrogen nucleophiles with aryl halides in water
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A facile and practical strategy has been developed for the N-arylation of nitrogen nucleophiles with aryl halides catalyzed by a combination of iron(III) chloride [FeCl3] and dimethylethylenediamine (dmeda) in water. A variety of nitrogen nucleophiles including pyrazole, indole, 7-azaindole and benzamide afforded the N-arylated products in the presence of the catalytic system (in up to 88% yield).
- Teo, Yong-Chua
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supporting information; experimental part
p. 720 - 724
(2009/11/30)
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- Cobalt-catalyzed N-arylation of nitrogen nucleophiles in water
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The first cobalt-catalyzed N-arylation of nitrogen heterocycles with electrophilic aryl halides in water mediated by a combination of readily available and cheap CoCl2·6H2O with the chelating diamine was reported. Investigation of the ligand system show that the reaction proceeds through a biphasic system with the best yield achieved when the reaction is carried out using a combination of CoCl2·6H 2O and N,N'-dimethylethylenediamine (dmeda). Aryl iodides are found to be more reactive than aryl bromides as electophilic counterpart in the coupling reactions, producing the products in much higher yields. Heterocycles, such as indole and 7-azaindole are found to be effective nucleophilic counterparts for the coupling process and produce N-phenyl derivatives.
- Teo, Yong-Chua,Chua, Guan-Leong
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supporting information; experimental part
p. 3072 - 3075
(2009/12/05)
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- IRON-COPPER CO-CATALYZED PROCESS FOR CARBON-CARBON OR CARBON-HETEROATOM BONDING
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The present invention relates to a process for creating a Carbon-Carbon bond (C-C) or a Carbon-Heteroatom bond (C -HE) by reacting a compound carrying a leaving group with a nucleophilic compound carrying a carbon atom or a heteroatom (HE) that can substitute for the leaving group, creating a C-C or C-HE bond, wherein the reaction takes place in the presence of an effective quantity of a catalytic system comprising iron and copper.
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Page/Page column 47-48
(2008/06/13)
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- Efficient iron/copper co-catalyzed arylation of nitrogen nucleophiles
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(Chemical Equation Presented) An ideal pair: Various substituted aryl halides react under mild conditions with nitrogen heterocycles in the presence of catalytic amounts of [Fe(acac)3] (acac = acetylacetonate) and copper salts to give the corresponding cross-coupling products in high yields (see scheme). This cheap and environmentally friendly cocatalyst system is the first example of cooperative Fe/Cu catalysis in this type of N-C bond formation.
- Taillefer, Marc,Xia, Ning,Ouali, Armelle
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p. 934 - 936
(2008/02/01)
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- Iron-catalyzed N-arylation of nitrogen nucleophiles
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(Chemical Equation Presented) Easy does it! A simple procedure for the N-arylation of nitrogen-containing heterocycles and primary amides relies on a catalyst formed in situ from inexpensive and environmentally benign FeCl 3 and a diamine ligand. The cross-coupling reaction with aryl halides provides N-arylated compounds in high yields (see scheme; R = H, Cl, Me, OMe, CO2Et, F, CF3).
- Correa, Arkaitz,Bolm, Carsten
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p. 8862 - 8865
(2008/09/19)
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