- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
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The present invention provides: a compound represented by chemical formula 1; an organic electric element comprising a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode; and an electronic device comprising the organic electric element. By comprising the compound represented by chemical formula 1 in the organic material layer, it is possible to lower a driving voltage, and improve luminous efficiency and a lifespan of the organic electric element.COPYRIGHT KIPO 2021
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Paragraph 0240-0243
(2020/11/26)
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- Hydrogenation of Borylated Arenes
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A cis-selective hydrogenation of abundant aryl boronic acids and their derivatives catalyzed by rhodium cyclic (alkyl)(amino)carbene (Rh–CAAC) is reported. The reaction tolerates a variety of boron-protecting groups and provides direct access to a broad s
- Wollenburg, Marco,Moock, Daniel,Glorius, Frank
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supporting information
p. 6549 - 6553
(2019/01/04)
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- C-H Borylation Catalysts that Distinguish between Similarly Sized Substituents like Fluorine and Hydrogen
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By modifying ligand steric and electronic profiles it is possible to C-H borylate ortho or meta to substituents in aromatic and heteroaromatic compounds, where steric differences between accessible C-H sites are small. Dramatic effects on selectivities between reactions using B2pin2 or 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin) are described for the first time. Judicious ligand and borane combinations give highly regioselective C-H borylations on substrates where typical borylation protocols afford poor selectivities.
- Miller, Susanne L.,Chotana, Ghayoor A.,Fritz, Jonathan A.,Chattopadhyay, Buddhadeb,Maleczka, Robert E.,Smith, Milton R.
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supporting information
p. 6388 - 6392
(2019/08/26)
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- A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions
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Herein, we present an air-stable dianthracenyl monophosphine ligand (diAnthPhos) which can be prepared in two steps from commercially available anthracene derivatives. The ligand exhibits excellent efficiency for palladium-catalyzed coupling reactions. In particular, Miyaura borylation of heterocycle-containing electrophiles can be facilitated employing the diAnthPhos ligand with a broad substrate scope and low catalyst loading. The valuable synthetic utility of the new ligand is further demonstrated by a one-pot Miyaura borylation/Suzuki coupling protocol for heteroaryl-containing substrates.
- Wang, Xin,Liu, Wei-Gang,Tung, Chen-Ho,Wu, Li-Zhu,Cong, Huan
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supporting information
p. 8158 - 8163
(2019/09/07)
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- Control Interlayer Stacking and Chemical Stability of Two-Dimensional Covalent Organic Frameworks via Steric Tuning
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Layer stacking and chemical stability are crucial for two-dimensional covalent organic frameworks (2D COFs), but are yet challenging to gain control. In this work, we demonstrate synthetic control of both the layer stacking and chemical stability of 2D COFs by managing interlayer steric hindrance via a multivariate (MTV) approach. By co-condensation of triamines with and without alkyl substituents (ethyl and isopropyl) and a di- or trialdehyde, a family of two-, three-, and four-component 2D COFs with AA, AB, or ABC stacking is prepared. The alkyl groups are periodically appended on the channel walls and their contents, which can be synthetically tuned by the MTV strategy, control the stacking model and chemical stability of 2D COFs by maximizing the total crystal stacking energy and protecting hydrolytically susceptible backbones through kinetic blocking. Specifically, the COFs with higher concentration of alkyl substituents adopt AB or ABC stacking, while lower amount of functionalities leads to the AA stacking. The COFs bearing high concentration of isopropyl groups represent the first identified COFs that can retain crystallinity and porosity in boiling 20 M NaOH solution. After postsynthetic metalation with an iridium complex, the 2,2′-bipyridyl-derived COFs can heterogeneously catalyze C-H borylation of arenes, whereas the COF with isopropyl groups exhibits much higher activity than the COFs with ethyl groups and nonsubstituents due to the increased porosity and chemical stability. This work underscores the opportunity in using steric hindrance to tune and control layer stacking, chemical stability and properties of 2D COFs.
- Wu, Xiaowei,Han, Xing,Liu, Yuhao,Liu, Yan,Cui, Yong
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supporting information
p. 16124 - 16133
(2018/11/23)
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- Paper-Based Colorimetric Sensor System for High-Throughput Screening of C?H Borylation
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A paper-based colorimetric sensor system (PBCSS) was developed to detect the amount of bis(pinacolato)diboron (B2Pin2) and applied as a high-throughput screening protocol in Ir-catalyzed C?H borylation. First, 96 ligands were screened for the borylation of benzene, and then 12 of them were selected and tested for five substrates. These reaction mixtures were spotted in the PBCSS, showing a blue-violet color. The value of the gray scale of each reaction was obtained from these colored spots and converted to the extent of conversion of B2Pin2. The extents of conversion of B2Pin2 obtained from the PBCSS showed good correlation with those obtained from gas chromatography analysis. In addition, the modified conversion using blank data showed good correlation with the yield of products.
- Kim, Han-Sung,Eom, Min Sik,Han, Min Su,Lee, Sunwoo
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supporting information
p. 6282 - 6285
(2017/05/12)
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- C-H borylation by platinum catalysis
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Herein, we describe the platinum-catalyzed borylation of aromatic C-H bonds. N-Heterocyclic carbene-ligated platinum catalysts are found to be efficient catalysts for the borylation of aromatic C(sp2)-H bonds when bis(pinacolato)diboron is used as the boron source. The most remarkable feature of these Pt catalysts is their lack of sensitivity towards the degree of steric hindrance around the C-H bonds undergoing the borylation reaction. These Pt catalysts allow for the synthesis of sterically congested 2,6-disubstituted phenylboronic esters, which are otherwise difficult to synthesize using existing C-H borylation methods. Furthermore, platinum catalysis allows for the site-selective borylation of the C-H bonds ortho to fluorine substituents in fluoroarene systems. Preliminary mechanistic studies and work towards the synthetic application of this platinum catalyzed C-H borylation process are described.
- Furukawa, Takayuki,Tobisu, Mamoru,Chatani, Naoto
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p. 332 - 342
(2017/05/09)
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- Iridium-bipyridine periodic mesoporous organosilica catalyzed direct C-H borylation using a pinacolborane
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Heterogeneous catalysis for direct C-H borylation of arenes and heteroarenes in the combination of iridium (Ir) complex fixed on periodic mesoporous organosilica containing bipyridine ligands within the framework (Ir-BPy-PMO) and pinacolborane (HBpin) is reported. Ir-BPy-PMO showed higher catalytic activity toward the borylation of benzene with inexpensive HBpin compared to expensive bis(pinacolato)diboron (B2pin2). The precatalyst could be handled without the use of a glove box. The catalyst was easily recovered from reaction mixtures by simple filtration under air. The recovered catalyst still showed good catalytic activity for at least three more times for the borylation of benzene. A variety of arenes and heteroarenes were successfully borylated with high boron efficiency by Ir-BPy-PMO using HBpin, whereas almost no activity was observed for borylation of some heteroarenes with B2pin2. The system using Ir-BPy-PMO and HBpin was also utilized in syntheses of multi-boronated thiophene-based building blocks containing ladder-, acenefused-, and fused-thiophene skeletons. The combination of a stable and reusable solid catalyst and inexpensive HBpin is expected to be superior to conventional approaches for the development of industrial applications.
- Maegawa, Yoshifumi,Inagaki, Shinji
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supporting information
p. 13007 - 13016
(2016/01/09)
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- C-H Functionalization at Sterically Congested Positions by the Platinum-Catalyzed Borylation of Arenes
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Despite significant progress in the area of C-H bond functionalization of arenes, no general method has been reported for the functionalization of C-H bonds at the sterically encumbered positions of simple arenes, such as mesitylene. Herein, we report the development of the first platinum-based catalyst for C-H borylation of arenes and heteroarenes. Notably, this method exhibited high tolerance toward steric hindrance and provided rapid access to a series of 2,6-disubstituted phenylboronic esters, valuable building blocks for further elaborations.
- Furukawa, Takayuki,Tobisu, Mamoru,Chatani, Naoto
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supporting information
p. 12211 - 12214
(2015/10/12)
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- Fluorine-controlled C-H borylation of arenes catalyzed by a PSiN-pincer platinum complex
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An efficient, regioselective synthesis of fluorine-substituted arylboronic esters was achieved through fluorine-controlled C-H borylation of arenes with diboron catalyzed by a PSiN-platinum complex. The promising utility of the PSiN-platinum catalyst and its unique regioselectivity were demonstrated for the first time, which would complement the well-developed Ir-catalyzed C-H borylation.
- Takaya, Jun,Ito, Shisei,Nomoto, Hironori,Saito, Narumasa,Kirai, Naohiro,Iwasawa, Nobuharu
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supporting information
p. 17662 - 17665
(2015/12/18)
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- Continuous-Flow C-H borylation of arene derivatives
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A new continuous-flow system for C-H borylation has been developed. An insoluble catalyst prepared from chloro(1,5-cyclooctadien)iridium(I) dimer and 2,2′-bipyridine-4,4′-dicarboxylic acid in the presence of bis(pinacolato)diboron exhibited high reactivity under continuous-flow processing without the loss of expensive iridium metal.
- Tagata, Tsuyoshi,Nishida, Mayumi,Nishida, Atsushi
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experimental part
p. 1662 - 1666
(2010/09/15)
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- BENZOFURANYL- AND BENZOTHIENYL- PIPERAZINYL QUINOLINES AND METHODS OF THEIR USE
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Benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives and compositions containing such compounds are disclosed. Methods of using benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives and compositions containing such composition in the treatment and/or prevention of serotonin-related disorders, such as depression and anxiety, are also disclosed. In addition, processes for the preparation of benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives are disclosed.
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Page/Page column 17
(2009/04/24)
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- Ir-catalyzed functionalization of 2-substituted indoles at the 7-position: Nitrogen-directed aromatic borylation
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Ir-catalyzed borylation of 2-substituted indoles selectively yields 7-borylated products in good yields. N-Protection, required for previous functionalizations of 2-substituted indoles, is unnecessary. Copyright
- Paul, Sulagna,Chotana, Ghayoor A.,Holmes, Daniel,Reichle, Rebecca C.,Maleczka Jr., Robert E.,Smith III, Milton R.
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p. 15552 - 15553
(2007/10/03)
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- BENZOFURANYL-AND BENZOTHIENYL-PIPERAZINYL QUINOLINES AND METHODS OF THEIR USE
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Benzofuranyl-and benzothienyl-piperzinyl quinoline derivatives and compositions containing such compounds are disclosed. Methods of using benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives and compositions containing such composition in the treatment and/or prevention of serotonin-related disorders, such as depression and anxiety, are also disclosed. In addition, processes for the preparation of benzofuranyl- and benzothienyl-piperzinyl quinoline derivatives are disclosed.
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- PROCESS FOR PRODUCTION OF HETEROARYL-TYPE BORON COMPOUNDS WITH IRIDIUM CATALYST
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The present invention provides an economically and industrially superior simple process that enables the selective production of an aromatic heterocyclic monoboron compound and aromatic heterocyclic diboron compound at a satisfactory yield and in a desired ratio by reacting an aromatic heterocyclic compound and a boron compound in a single step under mild conditions while changing only the charged ratios of the raw materials. The present invention provides a production process of a heteroaryl mono- or diboron compound comprising an aromatic heterocyclic compound and a boron compound in the form of bis(pinacolate)diboron or pinacolate diborane in the presence of a iridium-containing catalyst and a ligand such as a bipyridyl ligand.
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- Iridium-catalyzed C-H coupling reaction of heteroaromatic compounds with bis(pinacolato)diboron: Regioselective synthesis of heteroarylboronates
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The C-H coupling of aromatic heterocycles with bis(pinacolato)diboron was carried out in octane at 80-100°C in the presence of a 1/2[IrCl(COD)]2-(4,4′-di-tert-butyl-2,2′-bipyridine) catalyst (3 mol%). The reactions of five-membered substrates such as thiophene, furan, pyrrole, and their benzo-fused derivatives exclusively produced 2-borylated products, whereas those of six-membered heterocycles including pyridine and quinoline selectively occurred at the 3-position. Regioselective synthesis of bis(boryl)heteroaromatics was also achieved by using an almost equimolar amount of substrates and the diboron.
- Takagi, Jun,Sato, Kazuaki,Hartwig, John F,Ishiyama, Tatsuo,Miyaura, Norio
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p. 5649 - 5651
(2007/10/03)
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- Synthesis of the diazonamide A macrocyclic core via a Dieckmann-type cyclization.
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[reaction: see text] Suzuki coupling of 18 and 30 affords 9 as an interconverting mixture of two atropisomers. Treatment with LDA at -23 degrees C affords the macrocyclic ketone 8 in 57% yield.
- Vedejs,Zajac
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p. 2451 - 2454
(2007/10/03)
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