• Title/Summary/Keyword: Carbon-carbon coupling reaction

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Palladium-Catalyzed Coupling between Quinolone Moieties and Heteroaryl Stannes - Synthesis of C-7 heteroaryl Quinolone Derivatives - (팔라듐 촉매를 이용한 퀴놀론핵과 Heteroaryl Stannes의 결합 - C-7 heteroaryl 쿼놀론 유도체의 합성 -)

  • 남상훈;함원훈;김기수;임태균;양재권
    • YAKHAK HOEJI
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    • v.37 no.6
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    • pp.615-620
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    • 1993
  • The cross-coupling reaction of organo tin reagents with a variety of organic halides, catalyzed by palladium, provides a novel method for generating a carbon-carbon bond. We used this method for the antibacterial agents, and synthesis of new quinolone derivatives which have carbon-carbon bond at C-7 position of general quinolone moieties. Aryl tin, quinolone moieties, and palladium catalyst were refluxed in DMF to afford new quinolone derivatives. This palladium catalyzed coupling reactions have capacity for further synthetic elaboration.

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Palladium-Catalyzed Coupling between Quinolone Moieties and Heteroacyl Stannes - Synthesis of C-7 Heteroacyl Quinolone Derivatives

  • 함원훈;양재권;임태균
    • Proceedings of the Korean Society of Applied Pharmacology
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    • 1994.04a
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    • pp.221-221
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    • 1994
  • The cross-coupling reaction of organo tin reagents with a variety of organic halides, catalyzed by palladium, provides a novel method for generating a carbon-carbon bond. We use this method for antibacterial agents, and synthesis of new quinolone derivatives which have carbon-carbon bond at C-7 position of general quinolone moieties. Aryl tin, quinolone moieties, and palladium catalyst were refluxed in DMF to afford new quinolone derivatives. This palladium catalyzed coupling reactions have capacity for further synthetic elaboration.

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Ligand Effect in Recycled CNT-Pd Heterogeneous Catalyst for Decarboxylative Coupling Reactions

  • Kim, Ji Dang;Pyo, Ayoung;Park, Kyungho;Kim, Gwui Cheol;Lee, Sunwoo;Choi, Hyun Chul
    • Bulletin of the Korean Chemical Society
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    • v.34 no.7
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    • pp.2099-2104
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    • 2013
  • We present here an efficient and simple method for preparation of highly active Pd heterogeneous catalyst (CNT-Pd), specifically by reaction of dichlorobis(triphenylphosphine)palladium ($Pd(PPh_3)_2Cl_2$) with thiolated carbon nanotubes (CNTs). The as-prepared CNT-Pd catalysts demonstrated an excellent catalytic activity for the carbon-carbon (C-C) cross-coupling reactions (i.e. Suzuki, Stille, and decarboxylative coupling reactions) under mild conditions. The CNT-Pd catalyst could easily be removed from the reaction mixture; additionally, in the decarboxylative coupling of iodobenzene and phenylpropiolic acid, it showed a six-times recyclability, with no loss of activity. Moreover, once its activity had decreased by repeated recycling, it could easily be reactivated by the addition of phosphine ligands. The remarkable recyclability of the decarboxylative coupling reaction is attributable to the high degree of dispersion of Pd catalysts in CNTs. Aggregation of the Pd catalysts is inhibited by their strong adhesion to the thiolated CNTs during the chemical reactions, thereby permitting their recycling.

Synthesis and Characterization of Graphene and Graphene Oxide Based Palladium Nanocomposites and Their Catalytic Applications in Carbon-Carbon Cross-Coupling Reactions

  • Lee, Minjae;Kim, Bo-Hyun;Lee, Yuna;Kim, Beom-Tae;Park, Joon B.
    • Bulletin of the Korean Chemical Society
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    • v.35 no.7
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    • pp.1979-1984
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    • 2014
  • We have developed an efficient method to generate highly active Pd and PdO nanoparticles (NPs) dispersed on graphene and graphene oxide (GO) by an impregnation method combined with thermal treatments in $H_2$ and $O_2$ gas flows, respectively. The Pd NPs supported on graphene (Pd/G) and the PdO NPs supported on GO (PdO/GO) demonstrated excellent carbon-carbon cross-coupling reactions under a solvent-free, environmentally-friendly condition. The morphological and chemical structures of PdO/GO and Pd/G were fully characterized using X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), and transmission electron microscopy (TEM). We found that the remarkable reactivity of the Pd/G and PdO/GO catalysts toward the cross-coupling reaction is attributed to the high degree of dispersion of the Pd and PdO NPs while the oxidative states of Pd and the oxygen functionalities of graphene oxide are not critical for their catalytic performance.

Synthesis of Diaryl $\alpha$-Diketones via Palladium Catalyzed Double Carbonylative Homo Coupling of Aryl Iodides with Carbon Monoxide

  • Kim Jin Il;Kim Nam Jung;Ryu Cheol Mo
    • Bulletin of the Korean Chemical Society
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    • v.9 no.1
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    • pp.30-32
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    • 1988
  • Symmetrical diaryl ${\alpha}-diketones$ were synthesized in moderately good yields through the palladium catalyzed reaction of aryl iodides with carbon monoxide. The reaction was tolerant of a wide variety of fuctionalities($OCH_3,\;CH_3,\;NO_2,\;OH,\;COOH$) on the aryl iodide. On the other hand, the similar reaction of aryl bromides or chlorides with carbon monoxide did not proceed.

Palladium-Catalyzed Carbonylative Coupling of Aryl Iodide and Diethylmalonate (팔라듐 촉매를 이용한 요오드화 방향족 화합물과 Diethylmalonate 와의 CO 첨가 커플링반응)

  • Jin Il Kim;Kwang Hyek Lee;Tae Soon Yoon
    • Journal of the Korean Chemical Society
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    • v.33 no.5
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    • pp.530-537
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    • 1989
  • Diethylbenzoylmalonates with various substituents were synthesized in moderately good yields through palladium-catalyzed carbonylative coupling of aryl iodide and diethylmalonate with carbon monoxide. Palladium-catalyzed carbonylative coupling reaction usually proceeded well in polar aprotic solvents in the presence of three equivalents of inorganic bases and palladium(II) catalyst. When the reaction was carried out under 10 atm pressure of carbon monoxide, the yield of diethylbenzoylmalonate derivatives was much better than that of reaction under atomspheric pressure of carbon monoxide.

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A Convenient Synthesis of an Anti-Helicobacter Pylori Agent, Dehydrodiconiferyl Alcohol

  • Hu, Kun;Jeong, Jin-Hyun
    • Archives of Pharmacal Research
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    • v.29 no.7
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    • pp.563-565
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    • 2006
  • Potential anti-Helicobacter pylori agent dehydrodiconiferyl alcohol was synthesized in 44% overall yield, starting from vanillin which could be commercially available. Carbon extension of vanillin followed by the Horner-Wadsworth-Emmons reaction, a biomolecular radical coupling reaction and DIBAL-H reduction gave dehydrodiconiferyl alcohol.

Immobilization of Lipase on Single Walled Carbon Nanotubes in Ionic Liquid

  • Lee, Han-Ki;Lee, Jae-Kwan;Kim, Mahn-Joo;Lee, Cheol-Jin
    • Bulletin of the Korean Chemical Society
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    • v.31 no.3
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    • pp.650-652
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    • 2010
  • A lipase from Pseudomonas cepacia was immobilized onto single walled carbon nanotubes (SWNTs) in two different ways in each of two solvent systems (buffer and ionic liquid). The most efficient immobilization was achieved in ionic liquid (1-butyl-3-methylimidazolium tetrafluoroborate, BMIM-$BF_4$). In this procedure, carbon nanotubes were first functionalized noncovalently with 1-pyrenebutyric acid N-hydroxysuccinimide ester and then subject to the coupling reaction with the lipase in ionic liquid. The resulting immobilized enzyme displayed the highest activity in the transesterification of 1-phenylethyl alcohol in the presence of vinyl acetate in toluene.

Coupling Reaction of CO2 with Epoxides by Binary Catalytic System of Lewis Acids and Onium Salts

  • Bok, Taekki;Noh, Eun Kyung;Lee, Bun Yeoul
    • Bulletin of the Korean Chemical Society
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    • v.27 no.8
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    • pp.1171-1174
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    • 2006
  • Various off-the-shelf Lewis acids in conjunction with various onium salts are screened for coupling reaction of $CO_2$ with epoxides. Among the tested ones, $VCl_3/n-Bu_4NOAc$, $VCl_3/(n-Bu_4NCl$ or PPNCl), $FeCl_3/ n-Bu_4NOAc$, and $FeCl_3/ n-Bu_4NOAc$are proved to be highly active. Propylene oxide, epichlorohydrin, styrene oxide, and cyclohexene oxide can be converted over 90% yields to the corresponding cyclic carbonates without the use of organic solvents under mild conditions by 0.1-1.0 mol% catalyst charge.