• Title/Summary/Keyword: Terminal alkynes

Search Result 9, Processing Time 0.041 seconds

Solvent-free Synthesis of Propargylic Alcohols using ZnO as a New and Reusable Catalyst by Direct Addition of Alkynes to Aldehydes

  • Hosseini-Sarvari, Mona;Mardaneh, Zahra
    • Bulletin of the Korean Chemical Society
    • /
    • v.32 no.12
    • /
    • pp.4297-4303
    • /
    • 2011
  • Under solvent-free conditions, the synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes promoted by ZnO as a novel, commercially, and cheap catalyst is described. Furthermore, the catalyst can be reused for several times without any significant loss of its catalytic activity.

Chemistry of Ruthenium Hydridonitrosyl Complexes Containing Chelating Triphosphines IV-Reactions between RuH(NO)(Cyttp) and Alkynes (Cyttp: Bis(dicyclohexylphosphino-propyl)phenylphosphine)

  • Ik-Mo Lee;Ook-Jae Cho;Devon W. Meek;Chan-Yong Kim
    • Bulletin of the Korean Chemical Society
    • /
    • v.14 no.5
    • /
    • pp.625-631
    • /
    • 1993
  • The types of the products of the reactions between RuH(NO)(Cyttp) and alkynes are sensitive to the nature of alkynes. Terminal, nonactivated alkynes (HC${\equiv}$CR, R=Ph, hexyl and $CH_2OH)$ produce acetylide complexes and terminal (HC${\equiv}$CR, R=C(O)Me, COOEt) or internal activated ones (RC${\equiv}$ CR, R=COOMe) lead to form alkenyl complexes. On the other hand, internal nonactivated alkynes (RC${\equiv}$CR, R=Ph) do not show reactivity toward RuH(NO)(Cyttp). These products can be rationalized by the cis-concerted mechanism but the radical pathway appears to work in the reaction of propargyl chloride. From the spectroscopic data, the trigonal bipyramidal structure with a linear NO group is proposed for these products.

Synthesis of 2-Substituted Benzofurans from o-Iodophenols and Terminal Alkynes with a Recyclable Palladium Catalyst Supported on Nano-sized Carbon Balls under Copper- and Ligand-Free Conditions

  • Yum, Eul Kgun;Yang, Ok-Kyung;Kim, Ji-Eun;Park, Hee Jung
    • Bulletin of the Korean Chemical Society
    • /
    • v.34 no.9
    • /
    • pp.2645-2649
    • /
    • 2013
  • We have developed a one-step synthesis of benzofurans from o-iodophenol and various terminal alkynes, by using Pd catalyst supported on nano-sized carbon balls (NCB) under copper- and ligand free conditions. This recyclable catalyst could be reused more than 5 times in the same heteroannulation reaction. The results have demonstrated that diverse 2-substituted benzofurans with tolerant functional groups can be prepared simply and conveniently under these conditions.

Synthesis, Reactions and Catalytic Activities of Water Soluble Rhodium and Iridium-Sulfonated Triphenylphosphine Complexes. 1. Polymerization of Terminal Alkynes

  • 주광석;김상열;진종식
    • Bulletin of the Korean Chemical Society
    • /
    • v.18 no.12
    • /
    • pp.1296-1301
    • /
    • 1997
  • Polymerization of terminal alkynes (phenlacetylene and 4-ethynyltoluene) catalyzed by water soluble rhodium (Ⅰ) complex, RhCl(CO)(TPPTS)2 (TPPTS=m-P(C6H4SO3Na)3) (1) selectively produces cis-transoid polymers at room temperature in homogeneous solution of H2O and MeOH as well as in biphasic solutions of H2O and CHCl3. The rate of polymerization is higher in H2O/MeOH than in H2O/CHCl3. The iridium analog, IrCl(CO)(TPPTS)2 (2) shows catalytic activity for the polymerization of phenylacetylene only at elevated temperature to give trans-polymers. The polymerization rate increases significantly when the trimethylamine N-oxide (Me3NO) was added to the reaction mixtures. The electronic absorption spectra of the cis-transoid polymers show three absorption bands whereas the trasn-polymers show only one absorption band. It seems that the electronic absorption bands depend on the configuration of the polymers.

Entry to Highly Hindered Chiral β-Amino Triazoles Bearing a gem-Diaryl Group by Azide-alkyne Click Chemistry

  • Sadu, Venkata Subbaiah;Roy, Harendra Nath;Arigala, Pitchaiah;Hwang, In-Taek;Lee, Kee-In
    • Bulletin of the Korean Chemical Society
    • /
    • v.35 no.6
    • /
    • pp.1605-1612
    • /
    • 2014
  • Copper(I)-catalyzed Huisgen cycloaddition of terminal alkynes with unmasked azidoamines derived from amino acids is described. The reported strategy provides a new entry to highly hindered ${\beta}$-amino 1,2,3-triazole derivatives bearing a gem-diaryl group, which are potentially valuable entities as molecular catalysts for asymmetric transformations.

Preparation, Reactions and Catalytic Activities of Water Soluble Iridium-Sulfonated Triphenylphosphine Complex

  • 진종식;장원태;양서균;주광석
    • Bulletin of the Korean Chemical Society
    • /
    • v.18 no.3
    • /
    • pp.324-327
    • /
    • 1997
  • Water soluble iridium complex, IrCl(CO)(TPPTS)2·χH2O (1) (TPPTS=m-trisulfonated triphenylphosphine) has been prepared from the reaction of a water soluble complex, IrCl(COD)(TPPTS)2·6H2O (COD=l,5-cyclooctadiene) with CO and unambiguously characterized by electronic absorption, 31P NMR, 13C NMR and IR spectral data. Complex 1 catalyzes the hydration of terminal alkynes to give ketones in aqueous solutions at room temperature. The rate of PhC≡CH hydration dramatically increases with addition of MeOH to the reaction mixture in H2O, which is understood in terms of i) the excellent miscibility between H2O and MeOH and ii) the assumed catalytic hydration pathway involving the initial formation of (alkyne)IrCl(CO)(TPPTS)2.

Indium and Gallium-Mediated Addition Reactions

  • Lee, Phil-Ho
    • Bulletin of the Korean Chemical Society
    • /
    • v.28 no.1
    • /
    • pp.17-28
    • /
    • 2007
  • Indium and gallium have emerged as useful metals in organic synthesis as a result of its intriguing chemical properties of reactivity, selectivity, and low toxicity. Although indium belongs to a main metal in group 13, its first ionization potential energy is very low and stable in H2O and O2. Therefore, indium-mediated organic reactions are of our current interest. On the basis of these properties of indium, many efficient indium-mediated organic reactions have been recently developed, such as the addition reactions of allylindium to carbonyl and iminium groups, the indium-mediated synthesis of 2-(2-hydroxyethyl)homoallenylsilanes, the indiummediated allylation of keto esters with allyl halides, sonochemical Reformatsky reaction using indium, the indium-mediated selective introduction of allenyl and propargyl groups at C-4 position of 2-azetidinones, the indium-mediated Michael addition and Hosomi-Sakurai reactions, the indium-mediated β-allylation, β- propargylation and β-allenylation onto α,β-unsaturated ketones, the highly efficient 1,4-addition of 1,3-diesters to conjugated enones by indium and TMSCl, and the intramolecular carboindation reactions. Also, we found gallium-mediated organic reactions such as addition reactions of propargylgallium to carbonyl group and regioselective allylgallation of terminal alkynes.