• Title/Summary/Keyword: Sonogashira reaction

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High Catalytic Activity and Recyclability of Graphene Oxide Based Palladium Nanocomposites in Sonogashira Reaction

  • Kim, Bo Hyun;Park, Joon B.
    • Proceedings of the Korean Vacuum Society Conference
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    • 2013.08a
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    • pp.139.1-139.1
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    • 2013
  • Graphene and graphene oxide (GO) have been modified with palladium nanoparticles (Pd NPs) to develop high performance catalysts for the Sonogashira cross coupling reaction. To understand catalytic performance of Pd NPs on graphene (Pd/G) and Pd NPs on GO (Pd/GO), we monitored their morphological and electronic structural changes before/after Sonogashira reaction using FT-IR, XRD, XPS, and XAFS. Here, we demonstrate that both Pd/G and Pd/GO show high catalytic efficiency toward the Sonogashira reaction, but only Pd/GO revealed excellent recyclability. The remarkable catalytic efficiency of both catalysts is attributed to the high degree of the Pd NP dispersions on supports and thus smaller Pd NPs can provide highly reactive low coordinated Pd atoms. However, we attributed the excellent recyclability of Pd/GO to the presence of oxygen functionalities on GO, which can provide nucleation sites for the detached Pd atoms during the Sonogashira reaction and prevent agglomeration of the Pd NPs since the oxygen functional groups are very reactive to mobile Pd adatoms.

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Facile Synthesis of Natural Moracin Compounds using Pd(OAc)2/P(tBu)3-HBF4 as a Sonogashira Coupling Reagent

  • Lee, Jae Jun;Yun, So-Ra;Jun, Jong-Gab
    • Bulletin of the Korean Chemical Society
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    • v.35 no.12
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    • pp.3453-3458
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    • 2014
  • An efficient and practical synthesis of natural moracins, which have diverse range of biological properties including anticancer, antioxidant, and antibacterial activities, has been achieved using $Pd(OAc)_2/P(^tBu)_3-HBF_4$ as a Sonogashira coupling reagent which solved the unreactive problems in case of higher electron density of haloaryl compounds in the reaction. Lowering electron density of halophenol with acetylation and changing Sonogashira coupling reagent from $PdCl_2(PPh_3)_2$ to $Pd(OAc)_2/P(^tBu)_3-HBF_4$ smoothly produce the benzofuran structures in the syntheses of moracins M, N and S. The electron deficient halobenzaldehyde, however, easily forms the benzofuran using original Sonogashira conditions, and utilized for the first synthesis of moracin Y.

Preparation, Characterization, and Catalytic Applications of Graphene-palladium Nanocomposites

  • Hong, Yeong-Guk;Yu, Se-Hui;Park, Jun-Beom
    • Proceedings of the Korean Vacuum Society Conference
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    • 2012.02a
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    • pp.262-262
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    • 2012
  • Modifications of graphenes have been studied for catalytic applications due to their advantages such as high surface area, conductivity and thermal stability. In this research, individual graphene oxide (GO) sheets were exfoliated from graphite using Hummers and Offeman method. Pd nano-particles were deposited on the GO surface using Pd2+ ion exchange where hydroxyl groups on the GO act as nucleation sites of Pd nanoparticles and their dispersions. The thermal treatments of the Pd-GO in H2 flow produced Pd-Graphene nanocomposites. Their catalytic performances in Sonogashira reaction were investigated. Morphological and chemical structures of the GO, Pd-GO, and Pd-Graphene were investigated using FT-IR, XRD, TEM, STEM, and XPS. The catalytic performances have been investigated using microwave reactor.

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Preparation of fluorescent nucleic acids generating unique emission by primer extension reaction using pyrene-labeled deoxyuridine triphosphate derivatives

  • Takada, Tadao;Tanimizu, Yosuke;Nakamura, Mitsunobu;Yamana, Kazushige
    • Rapid Communication in Photoscience
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    • v.3 no.4
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    • pp.76-78
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    • 2014
  • Fluorescent nucleic acids were prepared utilizing the polymerase extension (PEX) reaction to incorporate fluorescent molecules. 2'-Deoxyuridine triphosphate (dUTP) derivatives possessing pyrene molecules as fluorophores were synthesized using the aqueous-phase Sonogashira coupling between 5-Iodo-dUTP and acetylene-linked pyrene molecules. The incorporation of the pyrene (Py)-labeled deoxyuridine triphosphates (PyU) into DNA by polymerase was evaluated by polyacrylamide gel electrophoresis, demonstrating that the PyU can work as a good substrate for the PEX reaction. The fluorescent properties of the functionalized DNA prepared by the PEX reaction were characterized by steady-state fluorescence measurements. The Py-conjugated DNA showed typical emission spectra of the pyrene, and the DNA with two pyrene molecules connected to each other by a diethylene glycol linker exhibited a broadened emission attributed to the electronic interaction between the Py molecules.

Solution Processable Symmetric 4-Alkylethynylbenzene End-Capped Anthracene Derivatives

  • Jang, Sang-Hun;Kim, Hyun-Jin;Hwang, Min-Ji;Jeong, Eun-Bin;Yun, Hui-Jun;Lee, Dong-Hoon;Kim, Yun-Hi;Park, Chan-Eon;Yoon, Yong-Jin;Kwon, Soon-Ki;Lee, Sang-Gyeong
    • Bulletin of the Korean Chemical Society
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    • v.33 no.2
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    • pp.541-548
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    • 2012
  • New candidates composed of anthracene and 4-alkylethynylbenzene end-capped oligomers for OTFTs were synthesized under Sonogashira coupling reaction conditions. All oligomers were characterized by FT-IR, mass, UV-visible, and PL emission spectrum analyses, cyclic voltammetry (CV), differential scanning calorimetry (DSC), thermal gravimetric analysis (TGA), $^1H$-NMR, and $^{13}C$-NMR. Investigation of their physical properties showed that the oligomers had high oxidation potential and thermal stability. Thin films of DHPEAnt and DDPEAnt were characterized by spin coating them onto Si/$SiO_2$ to fabricate top-contact OTFTs. The devices prepared using DHPEAnt and DDPEAnt showed hole field-effect mobilities of $4.0{\times}10^{-3}cm^2$/Vs and $2.0{\times}10^{-3}cm^2$/Vs, respectively, for solution-processed OTFTs.

Synthesis and Characterization of a New p-type Amorphous Conjugated copolymer for Solution Process OTFT Material

  • Ju, Jin-Uk;Kang, Peng Tao;Chung, Dae-Sung;Kim, Yun-Hi;Park, Chan-Eon;Kwon, Soon-Ki
    • 한국정보디스플레이학회:학술대회논문집
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    • 2008.10a
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    • pp.844-846
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    • 2008
  • A new p-type conjugated copolymer, poly(9,10-diethynylanthracene-alt-9,9-didodecylfluorene (PDADF) was synthesized through a Sonogashira coupling reaction. A solution-processed thin film transistor device showed a carrier mobility value of $6.0\;{\times}\;10^{-4}\;cm^2/Vs$ with a threshold voltage of -17 V and a capacitance ($C_i$) of $10\;nF/cm^2$.

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Facile Preparation of 2-Arylbenzo[b]furan Molecules and Their Anti-inflammatory Effects

  • Hwang, Jung-Woon;Choi, Da-Hye;Jeon, Jae-Ho;Kim, Jin-Kyung;Jun, Jong-Gab
    • Bulletin of the Korean Chemical Society
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    • v.31 no.4
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    • pp.965-970
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    • 2010
  • An efficient and practical preparation of 2-arylbenzo[b]furan molecules including natural egonol, XH-14, ailanthoidol, and unnatural derivatives is demonstrated using Sonogashira coupling, iodine induced cyclization and Wittig reaction. Anti-inflammatory effects of the prepared benzo[b]furans were examined in lipopolysaccharide (LPS)-stimulated RAW 264-7 macrophages. The results showed that ailanthoidol, XH-14 and three other unnatural derivatives (9-10, 13) inhibited significantly the production of inflammatory mediator nitric oxide without showing cytotoxicity.