A Convenient Route to β,γ-Unsaturated Esters without Formation of the α,β-Isomers. Palladium-Catalyzed Alkoxycarbonylation of Allylic Halides under Alcohol-Potassium Carbonate Tow-Phase Conditions

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Author(s)

    • KIJI Jitsuo
    • Department of Materials Science, Faculty of Engineering, Tottori University
    • OKANO Tamon
    • Department of Materials Science, Faculty of Engineering, Tottori University
    • HIGASHIMAE Yukiko
    • Department of Materials Science, Faculty of Engineering, Tottori University
    • FUKUI Yasuyuki
    • Department of Materials Science, Faculty of Engineering, Tottori University

Abstract

Palladium-catalyzed, atmospheric pressure carbonylation of allylic halides under alcohol-potassium carbonate (liquid–solid) two-phase conditions affords <i>β</i>,<i>γ</i>-unsaturated esters without formation of the <i>α</i>,<i>β</i>-isomers. Phosphine-free palladium compounds such as Pd(OAc)<sub>2</sub> (<b>1</b>) and Na<sub>2</sub>[PdCl<sub>4</sub>] (<b>2</b>) are a convenient catalyst for this reaction. Presence of triphenylphosphine retards the carbonylation. A mixture of Pd(OAc)<sub>2</sub>-PPh<sub>3</sub> or [PdCl<sub>2</sub>(PPh<sub>3</sub>)<sub>2</sub>] (<b>3</b>) catalyzes the carbonylation under pressure.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 69(4), 1029-1031, 1996-04-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008902054
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • Data Source
    CJP  J-STAGE 
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