- In Situ Formation of Cationic π-Allylpalladium Precatalysts in Alcoholic Solvents: Application to C-N Bond Formation
-
We report an efficient Buchwald-Hartwig cross-coupling reaction in alcoholic solvent, in which a low catalyst loading showed excellent performance for coupling aryl halides (I, Br, and Cl) with a broad set of amines, amides, ureas, and carbamates under mild conditions. Mechanistically speaking, in a protic and polar medium, extremely bulky biarylphosphine ligands interact with the dimeric precatalyst [Pd(π-(R)-allyl)Cl]2 to form the corresponding cationic complexes [Pd(π-(R)-allyl)(L)]Cl in situ and spontaneously. The resulting precatalyst further evolves under basic conditions into the corresponding L-Pd(0) catalyst, which is commonly employed for cross-coupling reactions. This mechanistic study highlights the prominent role of alcoholic solvents for the formation of the active catalyst.
- Steinsoultz, Philippe,Bailly, Aurélien,Wagner, Patrick,Oliva, Estefania,Schmitt, Martine,Grimaud, Laurence,Bihel, Frédéric
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p. 560 - 567
(2022/01/03)
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- Visible-Light- And PPh3-Mediated Direct C-N Coupling of Nitroarenes and Boronic Acids at Ambient Temperature
-
We present here a metal-free, visible-light- and triphenylphosphine-mediated intermolecular, reductive amination between nitroarenes and boronic acids at ambient temperature without any photocatalyst. Mechanistically, a slow reduction of nitroarenes to a nitroso and, finally, a nitrene intermediate occurs that leads to the amination product with concomitant 1,2-aryl/-alkyl migration from a boronate complex. A wide range of nitroarenes underwent C-N coupling with aryl-/alkylboronic acids providing high yields.
- Manna, Kartic,Ganguly, Tanusree,Baitalik, Sujoy,Jana, Ranjan
-
supporting information
p. 8634 - 8639
(2021/11/01)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
-
The present invention provides a novel compound capable of improving light emitting efficiency, stability and lifespan of an element, an organic electric element using the same, and an electronic device thereof.
- -
-
Paragraph 0166-0174
(2021/03/09)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND A ELECTRONIC DEVICE THEREOF
-
In the present invention, provided is a novel compound capable of improving luminance efficiency, stability, and service life of an element, an organic electronic element using the same, and an electronic device thereof. By using the compound of the present invention, high luminance efficiency, low driving voltages, and high heat resistance of the element can be achieved, and color purity and service life of the element can be greatly improved.
- -
-
Paragraph 0103; 0106-0109
(2021/06/22)
-
- Iridium(III)-Catalyzed Tandem Annulation of Pyridine-Substituted Anilines and α-Cl Ketones for Obtaining 2-Arylindoles
-
A facile and expeditious protocol for the synthesis of 2-arylindole compounds from readily available N-(2-pyridyl)anilines and commercially available α-Cl ketones through iridium-catalyzed C-H activation and cyclization is reported here. As a complementary approach to the conventional strategies for indole synthesis, the transformation exhibits powerful reactivity, tolerates a large number of functional groups, and proceeds with good to excellent yields under mild conditions, providing a straightforward method to obtain structurally diverse and valuable indole scaffolds. Furthermore, the reaction could be easily scaled up to gram scale.
- Cui, Xin-Feng,Qiao, Xin,Wang, He-Song,Huang, Guo-Sheng
-
p. 13517 - 13528
(2020/12/15)
-
- Tunable Electrochemical C?N versus N?N Bond Formation of Nitrogen-Centered Radicals Enabled by Dehydrogenative Dearomatization: Biological Applications
-
Herein, an environmentally friendly electrochemical approach is reported that takes advantage of the captodative effect and delocalization effect to generate nitrogen-centered radicals (NCRs). By changing the reaction parameters of the electrode material and feedstock solubility, dearomatization enabled a selective dehydrogenative C?N versus N?N bond formation reaction. Hence, pyrido[1,2-a]benzimidazole and tetraarylhydrazine frameworks were prepared through a sustainable transition-metal- and exogenous oxidant-free strategy with broad generality. Bioactivity assays demonstrated that pyrido[1,2-a]benzimidazoles displayed antimicrobial activity and cytotoxicity against human cancer cells. Compound 21 exhibited good photochemical properties with a large Stokes shift (approximately 130 nm) and was successfully applied to subcellular imaging. A preliminary mechanism investigation and density functional theory (DFT) calculations revealed the possible reaction pathway.
- Chen, Jianbin,Cui, Yuezhi,Gao, Wei,Han, Xiaoxin,Hu, Wei,Lv, Shide,Ma, Li,Niu, Liwei,Wang, Jian-Yong,Wu, Yanwei,Zhou, Jianhua,Zhou, Mingyang
-
supporting information
p. 11583 - 11590
(2020/05/06)
-
- CuI/2-Aminopyridine 1-Oxide Catalyzed Amination of Aryl Chlorides with Aliphatic Amines
-
A class of 2-aminopyridine 1-oxides are discovered to be effective ligands for the Cu-catalyzed amination of less reactive (hetero)aryl chlorides. A wide range of functionalized (hetero)aryl chlorides reacted with various aliphatic amines to afford the desired products in good to excellent yields under the catalyst of CuI/2-aminopyridine 1-oxides. Furthermore, the catalyst system worked well for the coupling of cyclic secondary amines and N-methyl benzylamine with (hetero)aryl chlorides.
- Chen, Xiahong,He, Yongqiang,Liang, Yun,Liu, Wenjie,Wang, Deping,Xia, Xiaohong,Xu, Jiamin,Xu, Zhifeng,Zhang, Fuxing,Zhang, Xin
-
supporting information
p. 7486 - 7490
(2020/10/12)
-
- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
-
The present invention provides a novel compound capable of improving light emitting efficiency, stability, and lifespan of an element, an organic electronic element using same, and an electronic device for the same. In one aspect, the present invention provides a compound represented by the following chemical formula 1. The compounds according to the present invention by utilizing a light emitting device of high efficiency, low driving voltage, high heat resistance can be achieved, and the color purity of the device can greatly improve the service life.
- -
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Paragraph 0105-0109; 0111; 0112-0113
(2020/06/23)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND A ELECTRONIC DEVICE THEREOF
-
The present invention provides a novel compound capable of improving luminance efficiency, stability, and service life of an element, an organic electronic element using the same, and an electronic device thereof. By using the compound of the present invention, high luminance efficiency, low driving voltage, and high heat resistance of the element can be achieved, and color purity and service life of the element can be greatly improved.
- -
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Paragraph 0123; 0127-0131
(2020/06/24)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
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Discloses a novel compound capable of improving the luminous efficiency, stability and lifetime of an element, and an organic electronic element, or an electronic device using the same. (by machine translation)
- -
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Paragraph 0115-0119; 0121-0123
(2020/06/24)
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- COMPOUND FOR AN ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
-
The present invention provides a novel compound capable of improving light emitting efficiency, stability, and lifespan of an element, an organic electronic element using same, and an electronic device for the same. In one aspect, the present invention provides a compound represented by combination of chemical formula 1 and chemical formula 2. The compounds according to the present invention by utilizing a light emitting device of high efficiency, low driving voltage, high heat resistance can be achieved, and the color purity of the device can greatly improve the service life.
- -
-
Paragraph 0115-0122; 0124
(2020/07/28)
-
- PROSTACYCLIN RECEPTOR AGONIST
-
A compound represented by formula (I) or an isomer or a pharmaceutically acceptable salt thereof. The present invention also relates to an application of the same in preparing a drug for treating a disease related to a PGI2 receptor.
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Paragraph 0212-0214; 0283-0285
(2020/12/22)
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- Amine compound for inhibiting SSASASASASASASAO/VAP-1 and application thereof in medicine (by machine translation)
-
The invention relates to an amine compound serving as an amino urea-sensitive amine oxidase (SSASAO) and/or a vascular adhesion protein -1 (VAP AP AP-1) inhibitor and application thereof in medicine, and further relates to a pharmaceutical composition containing the compound. The compounds or pharmaceutical compositions described herein may be used to treat inflammation and/or inflammation related diseases, diabetes and/or diabetes-related diseases, psychiatric disorders, ischemic diseases, vascular diseases, fibrosis or tissue transplant rejection. (by machine translation)
- -
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Paragraph 0544; 0546-0548; 0603; 0605-0606
(2019/08/12)
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- Ruthenium-catalyzed synthesis of indole derivatives from: N -aryl-2-aminopyridines and alpha-carbonyl sulfoxonium ylides
-
Indole is a ubiquitous structural motif with important applications in many areas of chemistry. Given this, a simple and efficient Ru(ii)-catalyzed synthesis of indole via intermolecular annulation of N-aryl-2-aminopyridines and sulfoxonium ylides was proposed and accomplished. Excellent selectivity and good functional group tolerance of this transformation were observed. This protocol provides easy access to a wide variety of useful indoles in the presence of a commercially available [Ru(p-cymene)Cl2]2 catalyst. A possible mechanism for the reaction pathway was also proposed. More importantly, this reaction will offer a useful method for the construction of enantioenriched indole frameworks.
- Cui, Xin-Feng,Ban, Zi-Hui,Tian, Wa-Fa,Hu, Fang-Peng,Zhou, Xiao-Qiang,Ma, Hao-Jie,Zhan, Zhen-Zhen,Huang, Guo-Sheng
-
supporting information
p. 240 - 243
(2019/01/10)
-
- Catalyst-Free Synthesis of 2-Anilinoquinolines and 3-Hydroxyquinolines via Three-Component Reaction of Quinoline N-Oxides, Aryldiazonium Salts, and Acetonitrile
-
A rapid microwave-assisted, catalyst-free, three-component synthesis of various 2-anilinoquinolines from quinoline N-oxides and aryldiazonium salts in acetonitrile under microwave irradiation is reported. This reaction utilizes acetonitrile as a single nitrogen source and involves the formation of two new C-N bonds via the formal [3 + 2] cycloaddition reaction. In the case of 2-substituted quinolines, 3-hydroxyquinoline was observed as the main product via a 1,3 shift of the oxygen atom from N-oxide to the C3 position of quinolines.
- Dhiman, Ankit Kumar,Chandra, Devesh,Kumar, Rakesh,Sharma, Upendra
-
p. 6962 - 6969
(2019/06/14)
-
- Synthesis of 2-substituted indoles by iridium (III)-catalyzed C–]H functionalization of N-phenylpyridin-2-amines
-
A highly regioselective synthesis of 2-substituted indoles was realized through Ir(III)-catalyzed C–]H functionalization of N-phenylpyridin-2-amines followed by the reaction with sulfoxonium ylides and intramolecular cyclization under mild conditions. The reaction completed with broad range of substrate scopes and gave various 2-substituted indoles in up to 98% yields.
- Zhang, Lei,Chen, Junyu,Chen, Jinkang,Jin, Licheng,Zheng, Xiangyun,Jiang, Xinpeng,Yu, Chuanming
-
supporting information
p. 1053 - 1056
(2019/03/20)
-
- Cu-Catalyzed Couplings of Heteroaryl Primary Amines and (Hetero)aryl Bromides with 6-Hydroxypicolinamide Ligands
-
A family of 6-hydroxypicolinamide ligands have been identified as effective supporting ligands for Cu-catalyzed couplings of heteroaryl bromides and chlorides with heteroaryl primary amines. The C-N couplings are carried out at 80-120 °C in DMSO or sulfolane using K2CO3 or K3PO4 as the base with 2-10 mol % CuI and supporting ligand. The strength of the base was found to have an impact on the chemoselectivity and rate. The use of K2CO3 as the base enabled selective C-N coupling of aryl bromides over aryl chlorides with 2-5 mol % Cu at 80-120 °C. With K3PO4 as the base, aryl chlorides are capable of undergoing C-N coupling, though 5-10 mol % Cu is required at 120-130 °C. Members of the ligand family are straightforward to prepare in one step from 6-hydroxypicolinic acid and the corresponding anilines.
- Bernhardson, David J.,Widlicka, Daniel W.,Singer, Robert A.
-
p. 1538 - 1551
(2019/09/04)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND A ELECTRONIC DEVICE THEREOF
-
PURPOSE: A compound containing bisindole for an organic electronic element is provided to improve light emitting efficiency, heat resistance, color purity, and lifetime and to lower driving voltage. CONSTITUTION: A compound for an organic electronic element contains compounds of chemical formulas 1 and 2. The organic electronic element contains one or more organic layers containing the compound. The organic layers are formed of the compounds by a solution process. The organic electronic element sequentially comprises a first electrode, the organic layers, and a second electrode. The organic layers are selected among a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer. An electronic device comprises a display device containing the organic electronic element, and a control unit which drives the display device.
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-
Paragraph 0091; 0093; 0095-0097
(2019/03/30)
-
- "on Water" Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols
-
The Ullmann-type cross coupling of a variety of aromatic, aliphatic amines with aryl halides is reported using a CuI-based catalytic system in combination with an easily accessible prolinamide ligand in aqueous media. The method is mild and tolerant to air, moisture, and a wide range of functional groups, providing a novel way to access a variety of aminated products. Secondary amines like heteroaromatic amines and nucleobases have also been used, affording the corresponding coupling products in good to excellent yields. Moreover, this method has been employed for chemoselective C-N arylation of aminophenols and further utilized for the synthesis of carbazole natural products, avoiding the protection and deprotection steps.
- Chakraborti, Gargi,Paladhi, Sushovan,Mandal, Tirtha,Dash, Jyotirmayee
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p. 7347 - 7359
(2018/07/29)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND A ELECTRONIC DEVICE THEREOF
-
The present invention is to complete an element with low-voltage driving, high life expectancy, and high efficiency through development of a bisindole derivative compound for implementing an element with low-voltage driving, high life expectancy, and high efficiency, which are required characteristics of an organic electroluminescent element. A compound for an organic electronic element includes a compound of a chemical formula 1.COPYRIGHT KIPO 2018
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-
Paragraph 0104-0106
(2019/01/05)
-
- Iridium-Catalysed Cascade Synthesis of Oxindoles Using Diazo Compounds: A Quick Entry to C-7-Functionalized Oxindoles
-
A cascade iridium-catalysed oxindole synthesis was achieved using pyridyl-protected anilines and bis(2,2,2-trifluoroethyl) 2-diazomalonate. The developed protocol is simple and scalable, and has a broad scope and excellent regioselectivity. The pyridyl directing group can easily be removed. The method was further extended to give C-7-functionalized oxindole derivatives in a straightforward manner. The role of bis(2,2,2-trifluoroethyl) 2-diazomalonate for oxindole preparation has been explored.
- Karmakar, Ujjwal,Das, Debapratim,Samanta, Rajarshi
-
p. 2780 - 2788
(2017/05/29)
-
- METHOD FOR PRODUCING PHENYLAMINOPYRIDINE COMPOUND
-
PROBLEM TO BE SOLVED: To provide a technique which makes it possible to produce a phenylaminopyridine compound economically and efficiently under a milder condition than before, with the reduced number of steps, and by convenient operation. SOLUTION: A method for producing a phenylaminopyridine compound includes the step in which an aniline compound and a halogenated pyridine compound react with liquid comprising alkali metal in a reaction solvent to prepare a phenylaminopyridine compound. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2017,JPOandINPIT
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-
Paragraph 0064
(2018/02/24)
-
- A segmented flow platform for on-demand medicinal chemistry and compound synthesis in oscillating droplets
-
We report an automated flow chemistry platform that can efficiently perform a wide range of chemistries, including single/multi-phase and single/multi-step, with a reaction volume of just 14 μL. The breadth of compatible chemistries is successfully demonstrated and the desired products are characterized, isolated, and collected online by preparative HPLC/MS/ELSD.
- Hwang, Ye-Jin,Coley, Connor W.,Abolhasani, Milad,Marzinzik, Andreas L.,Koch, Guido,Spanka, Carsten,Lehmann, Hansjoerg,Jensen, Klavs F.
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p. 6649 - 6652
(2017/07/10)
-
- HISTONE DEMETHYLASE INHIBITORS
-
The present invention relates generally to compositions and methods for treating cancer and neoplastic disease. Provided herein are substituted pyrido[3,4-d]pyrimidin-4-one derivative compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for inhibition of histone demethylase. Furthermore, the subject compounds and compositions are useful for the treatment of cancer, such as prostate cancer, breast cancer, bladder cancer, lung cancer and/or melanoma and the like.
- -
-
Paragraph 00158
(2016/04/09)
-
- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
-
Provided are a novel compound which enhances luminous efficiency, stability, and lifespan of an element; an organic electric element using the same; and an electronic device thereof. The compound of the present invention is represented by chemical formula (1). The organic electric element comprises: a first electrode; a second electrode; and an organic layer positioned between the first electrode and the second electrode.COPYRIGHT KIPO 2016
- -
-
Paragraph 0224; 0230
(2017/01/26)
-
- Direct C-H alkylation and indole formation of anilines with diazo compounds under rhodium catalysis
-
The rhodium(iii)-catalyzed direct functionalization of aniline C-H bonds with α-diazo compounds is described. These transformations provide a facile construction of ortho-alkylated anilines with diazo malonates or highly substituted indoles with diazo acetoacetates.
- Mishra, Neeraj Kumar,Choi, Miji,Jo, Hyeim,Oh, Yongguk,Sharma, Satyasheel,Han, Sang Hoon,Jeong, Taejoo,Han, Sangil,Lee, Seok-Yong,Kim, In Su
-
supporting information
p. 17229 - 17232
(2015/12/05)
-
- Convenient copper-mediated Chan-Lam coupling of 2-aminopyridine: Facile synthesis of N-arylpyridin-2-amines
-
A new and practical process for the synthesis of N-arylpyridin-2-amine derivatives has been developed. Under the assistance of copper, the desired products were produced from commercially available 2-aminopyridine and aryl boronic acids in moderate to good yields with good functional group tolerance.
- Chen, Jianbin,Natte, Kishore,Man, Nikki Y.T.,Stewart, Scott G.,Wu, Xiao-Feng
-
supporting information
p. 4843 - 4847
(2015/07/20)
-
- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
-
The present invention provides a novel compound which can improve light emitting efficiency, stability, and life of an element, an organic electronic element using the same, and an electronic device thereof. The organic electronic element of the present invention comprises: a first electrode; a second electrode; and an organic matter layer located between the first electrode and the second electrode, wherein the organic matter layer consists of a light emitting auxiliary layer and a hole transport layer containing the compound of the present invention.
- -
-
Paragraph 0150; 0151; 0156
(2016/10/08)
-
- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
-
The present invention provides a novel compound which can improve the light emitting efficiency, stability, and lifespan of an element; an organic electronic element using the same; and an electronic device thereof. The organic electronic element comprises: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, wherein the compound is included in the organic layer.(110) Substrate(120) Positive electrode(130) Hole injection layer(140) Hole transporting layer(141) Buffer layer(150) Light emitting layer(151) Light-emitting assisting layer(160) Electron transfer layer(170) Electron injection layer(180) Negative electrodeCOPYRIGHT KIPO 2015
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-
Paragraph 0180; 0181; 0186
(2016/10/08)
-
- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
-
Provided in the present invention are a novel compound which can improve light emitting efficiency, stability, and life, an organic electronic element using the same, and an electronic device thereof. The organic electronic element is characterized by comprising a first electrode; a second electrode; and an organic substance layer located between the first electrode and the second electrode, wherein the compound is contained in the organic substance layer. The organic electronic element is characterized by having the compound contained in at least one layer among a hole injection layer, a hole transfer layer, an light emitting auxiliary layer, or a light emitting layer of an organic substance layer.(140) Hole transfer layer(141) Buffer layer(150) Light emitting layer(151) Auxiliary light emitting layer(160) Electron transfer layer(170) Electron injection layer(180) Negative electrode(130) Hole injection layer(120) Positive electrode(110) SubstrateCOPYRIGHT KIPO 2015
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-
Paragraph 0175; 0183
(2016/10/08)
-
- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
-
The present invention provides a novel compound which can improve light emitting efficiency, stability, and durability of an element, an organic electronic element, and an electronic device thereof. The organic electronic element comprises: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, wherein the compound is included in the organic layer.(110) Substrate(120) Positive electrode(130) Hole injection layer(140) Hole transfer layer(141) Buffer layer(150) Light emitting layer(151) Light-emitting assisting layer(160) Electron transfer layer(170) Electron injection layer(180) Negative electrodeCOPYRIGHT KIPO 2015
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-
Paragraph 0176; 0183-0184
(2016/10/09)
-
- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
-
The present invention provides a novel compound which can improve the light emitting efficiency, stability and lifetime of an element; an organic electronic element using the same; and an electronic device thereof. The organic electronic element comprises: a first electrode; a second electrode; and an organic layer located between the first electrode and the second electrode, wherein the compound is included in the organic layer.(110) Substrate(120) Positive electrode(130) Hole injection layer(140) Hole transporting layer(141) Buffer layer(150) Light emitting layer(151) Light-emitting assisting layer(160) Electron transfer layer(170) Electron injection layer(180) Negative electrodeCOPYRIGHT KIPO 2015
- -
-
Paragraph 0187; 0188; 0193
(2017/01/02)
-
- Ligand free copper-catalyzed N-arylation of heteroarylamines
-
An efficient protocol for ligand-free Cu-catalyzed N-arylation of heteroarylamines has been developed. With the use of 1% CuI, a wide range of aryl iodides and bromides coupled with heteroarylamines to afford the corresponding products in high yields. Further, this protocol is particularly suitable for reactions of the most hindered aryl iodides with 2-aminopyridines.
- Wang, Deping,Kuang, Daizhi,Zhang, Fuxing,Liu, Yang,Ning, Shunhua
-
supporting information
p. 7121 - 7123
(2015/01/08)
-
- C-H cycloamination of N-aryl-2-aminopyridines and N-arylamidines catalyzed by an in situ generated hypervalent iodine(iii) reagent
-
A metal-free synthesis of diversified pyrido[1,2-a]benzimidazoles and 1H-benzo[d]imidazoles from N-aryl-2-aminopyridines and N-arylamidines has been developed. The C-H cycloamination reaction was catalyzed by hypervalent iodine(iii) species generated in situ from iodobenzene (catalytic) and peracetic acid (stoichiometric). The reaction proceeded smoothly at ambient temperature to provide the corresponding N-heterocycles in good to excellent yields.
- He, Yimiao,Huang, Jinbo,Liang, Dongdong,Liu, Lanying,Zhu, Qiang
-
supporting information
p. 7352 - 7354
(2013/09/23)
-
- Design, optimization, and biological evaluation of novel keto-benzimidazoles as potent and selective inhibitors of phosphodiesterase 10A (PDE10A)
-
Our development of PDE10A inhibitors began with an HTS screening hit (1) that exhibited both high p-glycoprotein (P-gp) efflux ratios in rat and human and poor metabolic stability. On the basis of cocrystal structure of 1 in human PDE10A enzyme, we designed a novel keto-benzimidazole 26 with comparable PDE10A potency devoid of efflux liabilities. On target in vivo coverage of PDE10A in rat brain was assessed using our previously reported LC-MS/MS receptor occupancy (RO) technology. Compound 26 achieved 55% RO of PDE10A at 30 mg/kg po and covered PDE10A receptors in rat brain in a dose-dependent manner. Cocrystal structure of 26 in PDE10A confirmed the binding mode of the novel scaffold. Further optimization resulted in the identification of keto-benzimidazole 34, which showed an increased in vivo efficacy of 57% RO in rats at 10 mg/kg po and an improved in vivo rat clearance and oral bioavailability.
- Hu, Essa,Kunz, Roxanne K.,Chen, Ning,Rumfelt, Shannon,Siegmund, Aaron,Andrews, Kristin,Chmait, Samer,Zhao, Sharon,Davis, Carl,Chen, Hang,Lester-Zeiner, Dianna,Ma, Ji,Biorn, Christopher,Shi, Jianxia,Porter, Amy,Treanor, James,Allen, Jennifer R.
-
p. 8781 - 8792
(2013/12/04)
-
- Direct ortho arylation of 9-(pyridin-2-yl)-9 h-carbazoles bearing a removable directing group via palladium(II)-catalyzed C-H bond activation
-
A one-pot synthesis of ortho-arylated 9-(pyridin-2-yl)-9H-carbazoles via C-H bond activation is presented. Silver nitrate and tert-butyl alcohol were found to be the best oxidant and solvent for the process, respectively. The product yields are from modest to excellent, and the reaction showed sufficient functional group tolerance. p-Benzoquinone served as an important ligand for the transmetalation and reductive elimination steps in the catalytic process. The key intermediate of the reaction, a 9-(pyridin-2-yl)-9H-carbazole palladacycle, was isolated, and its structure was unequivocally confirmed by X-ray crystallography. No kinetic isotope effect (kH/kD = 1.00 ± 0.17) for the C-H bond activation step was observed. In addition, a Hammett experiment gave a negative ρ value,-2.16 ± 0.02. The directing group, pyridinyl, was demonstrated to be a removable functional group. Finally, a rational catalytic mechanism is presented on the basis of all experimental evidence.
- Chu, Jean-Ho,Wu, Chung-Chiu,Chang, Deng-Hsiang,Lee, Ya-Ming,Wu, Ming-Jung
-
supporting information
p. 272 - 282
(2013/02/25)
-
- Palladium-catalyzed oxidative alkynylation of arene C-H bond using the chelation-assisted strategy
-
Palladium-catalyzed alkynylation of arene C-H bonds with (triisopropylsilyl)acetylene was developed for the first time under oxidative conditions in the present study. Among various type of directing groups examined, the N-phenyl-2-aminopyridine skeleton was shown to be most effective and selective for the Pd-catalyzed direct alkynylation reaction, and the desired alkynylated products were obtained in moderate to good yields.
- Kim, Seok Hwan,Park, Sae Hume,Chang, Sukbok
-
supporting information; experimental part
p. 5162 - 5166
(2012/07/31)
-
- Nickel-catalyzed intermolecular codimerization of acrylates and alkynes
-
The linear codimerization of acrylates and alkynes to produce 1,3-dienes is successfully demonstrated using a nickel catalyst in association with 2-aminopyridine as an additive.
- Horie, Hiroaki,Koyama, Ichiro,Kurahashi, Takuya,Matsubara, Seijiro
-
supporting information; experimental part
p. 2658 - 2660
(2011/05/03)
-
- Synthesis of N-(2-pyridyl)indoles via Pd(II)-catalyzed oxidative coupling
-
Readily available Pd(II) chloride catalysts can catalyze selective and efficient oxidative coupling between N-aryl-2-aminopyridines and internal alkynes to yield N-(2-pyridyl)indoles. This process involves the ortho C-H activation of N-aryl-2-aminopyridines, and CuCl2 was used as an oxidant. Compared to our previously reported Rh(III)-catalyzed synthesis of this class of product, this method is advantageous with a wider scope of alkynes and cost-effective Pd(II) catalysts. Molecular oxygen can be used as a terminal oxidant.
- Chen, Jinlei,Pang, Qingyu,Sun, Yanbo,Li, Xingwei
-
supporting information; experimental part
p. 3523 - 3526
(2011/06/24)
-
- On the importance of an acid additive in the synthesis of pyrido[1,2-a]benzimidazoles by direct copper-catalyzed amination
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Not just an acid! An expedient and highly modular synthesis of 6-, 7-, and 8-substituted pyrido[1,2-a]benzimidazoles (4) has been developed by a direct intramolecular C-H amination of N-phenylpyridin-2-amines (3). Efficient C-H amination of 3 could only be achieved in the presence of catalytic copper and an acid additive. The type of acid (pKa) proved to be crucial for the catalysis. C-Cl aminations in N-(2-chloroaryl)pyridin-2-amines allow access to 9-substituted pyrido[1,2-a]benzimidazoles. Copyright
- Masters, Kye-Simeon,Rauws, Tom R. M.,Yadav, Ashok K.,Herrebout, Wouter A.,Van Der Veken, Benjamin,Maes, Bert U. W.
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supporting information; experimental part
p. 6315 - 6320
(2011/07/31)
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- Palladium(II)-Catalyzed One-Pot Syntheses of 9-(Pyridin-2-yl)-9H-carbazoles through a Tandem C-H Activation/C-X (X=C or N) Formation Process
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A new one-pot synthesis of 9-(pyridin-2-yl)-9H-carbazoles through the simultaneous C-H activation and palladium(II)-catalyzed cross-coupling of N-phenylpyridin-2-amines with potassium aryltrifluoroborates is presented. Silver acetate and 1,4-dioxane proved to be the best oxidant and solvent, respectively. The product yields fluctuated from modest to excellent and the reaction showed sufficient functional group tolerance. p-Benzoquinone served as an important ligand for the transmetalation and reductive elimination steps in the catalytic process. The kinetic isotope effects (kH/kD) for the first and second C-H activation/C-C or C-N formation steps were measured as 2.14 and 1.18, respectively. Finally, a rational catalytic mechanism is presented based on all experimental evidence. Thrown together to perform: A variety of N-pyridylcarbazoles were synthesized through concurrent C-H activation/coupling of N-phenylpyridin-2-amines with potassium aryltrifluoroborates (see scheme; BQ=p-benzoquinone). The catalytic mechanism was elucidated by the examination of X-ray crystal structures of PdII intermediates and key products, as well as control experiments and kinetic isotope effect studies. Copyright
- Chu, Jean-Ho,Lin, Pi-Shan,Lee, Ya-Ming,Shen, Wei-Ting,Wu, Ming-Jung
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supporting information; experimental part
p. 13613 - 13620
(2011/12/22)
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- General and mild preparation of 2-aminopyridines
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A general and facile one-pot amination procedure for the synthesis of 2-aminopyridines from the corresponding pyridine-N-oxides is presented as a mild alternative to SNAr chemistry. A variety of amines and heterocyclic-N-oxides participate effectively in this transformation which uses the phosphonium salt, PyBroP, as a means of substrate activation.
- Londregan, Allyn T.,Jennings, Sandra,Wei, Liuqing
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supporting information; experimental part
p. 5254 - 5257
(2011/02/24)
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- A direct intramolecular C-H amination reaction cocatalyzed by copper(II) and iron(III) as part of an efficient route for the synthesis of pyrido[1,2-a ]benzimidazoles from N-aryl-2-aminopyridines
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A novel and efficient synthesis of pyrido[1,2-a]benzimidazoles through direct intramolecular aromatic C-H amination of N-aryl-2-aminopyridines has been developed. The reaction, cocatalyzed by Cu(OAc)2 and Fe(NO 3)3?9H
- Wang, Honggen,Wang, Yong,Peng, Changlan,Zhang, Jiancun,Zhu, Qiang
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supporting information; experimental part
p. 13217 - 13219
(2010/11/04)
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- Rh(III)-catalyzed oxidative coupling of N -aryl-2-aminopyridine with alkynes and alkenes
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[RhCp*Cl2]2 (1-2 mol %) can catalyze the oxidative coupling of N-aryl-2-aminopyridines with alkynes and arylates to give N-(2-pyridyl)indoles and N-(2-pyridyl)quinolones, respectively, using Cu(OAc)2 as an oxidant. Coupling with styrenes gave mono- and/or disubstituted olefination products.
- Chen, Jinlei,Song, Guoyong,Pan, Cheng-Ling,Li, Xingwei
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supporting information; experimental part
p. 5426 - 5429
(2011/03/20)
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- Examination of the aromatic amination catalyzed by palladium on charcoal
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The Buchwald-Hartwig amination of aryl halides with secondary amines and functionalized aromatic amines catalyzed by solid-supported palladium is reported. The choices of ligand, base and solvent are crucial for the successful coupling. The ami-nation of aromatic iodides, bromides and chlorides can be easily achieved with palladium on charcoal in the presence of a biphenylphosphane-type ligand at 80-110 °C. In addition, the palladium on charcoal catalyst is easily separable after the reaction, and reusable several times with only small activity loss.
- Komaromi, Anna,Novak, Zoltan
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supporting information; experimental part
p. 1523 - 1532
(2010/08/19)
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- 3-piperidyl-4-oxoquinazoline derivatives and pharmaceutical compositions comprising the same
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3-piperidyl-4-oxoquinazoline derivatives are provided, which is represented by the formula (I): wherein R represents an amino group or a cyclic amino group such as dibenzoazepine, each of which is substituted with a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or the like, n is an integer of 1 to 3, R3and R4independently represents a hydrogen atom, a lower alkyl group, or the like, or a pharmaceutically acceptable salt thereof. Compounds (I) of the present invention have excellent MTP-inhibitory activity. Thus, these compounds not only inhibit formation of LDL that is a cause of arteriosclerotic diseases but also regulate TG, cholesterol, and lipoproteins such as LDL in the blood and regulate cellular lipids through regulation of MTP activity. They can also be used as a new type of preventive or therapeutic agents for hyperlipemia or arteriosclerotic diseases. Furthermore, they can be used as therapeutic or preventive agents for pancreatitis, obesity, hypercholesterolemia, and hypertriglyceridemia.
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- CHEMISTRY OF HETEROCYCLIC N-OXIDES AND RELATED COMPOUNDS. ACYLAMINATION OF PYRIDINE N-OXIDE BY ANILINE, p-ANISIDINE, AND THEIR N-p-TOSYL DERIVATIVES
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Acylamination of pyridine N-oxide by aniline, p-anisidine, and their tosyl derivatives was carried out in an alkaline medium in the presence of p-tosyl chloride.The reaction proceeds selectively with the formation of the corresponding 2-(N-p-tosyl)anilino- and 2-p-(N-p-tosyl)anisidino-pyridines.The reaction products were converted by acid hydrolysis into the corresponding 2-anilinopyridines.
- Kurbatov, Yu. V.,Solekhova, M. A.
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p. 749 - 751
(2007/10/02)
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