• Title/Summary/Keyword: Metal-mediated allylation

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Zinc Mediated Barbier Type Allylation of Cyclic Imides and Subsequent Coupling Reactions with Carbon Nucleophiles

  • Kang, Seok-Won;Heo, Eun-Young;Jun, Jong-Gab;Kim, Sung-Hoon
    • Bulletin of the Korean Chemical Society
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    • v.25 no.12
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    • pp.1924-1928
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    • 2004
  • Allylations of N-benzyl and N-methyl cyclic imides were accomplished successfully under mild Barbier type conditions using zinc metal, allyl bromide and catalytic amount of $PbBr_2$. Subsequent coupling reactions with some carbon nucleophiles afforded 1,2- and 1,4-addition products in moderate to high yields.

Indium and Gallium-Mediated Addition Reactions

  • Lee, Phil-Ho
    • Bulletin of the Korean Chemical Society
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    • v.28 no.1
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    • pp.17-28
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    • 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.