Palladium-catalyzed decarboxylation-allylation of allylic esters of α-substituted β-keto carboxylic, malonic, cyanoacetic, and nitroacetic acids

Jiro Tsuji, Toshiro Yamada, Ichiro Minami, Masami Yuhara, Mohammad Nisar, Isao Shimizu

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    Abstract

    Decarboxylation-allylation of allylic β-keto carboxylates using Pd(OAc)2-PPh3 or Pd2(dba)3·CHCl3-dppe as a catalyst proceeds smoothly to give α-allylated ketones. The reaction is highly regioselective. In some cases, diallylated ketones are obtained with allylic esters bearing an active proton(s). Also rhodium, molybdenum, and nickel complexes are active catalysts in this reaction. Similarly allylic esters of α-substituted malonates, cyanoacetates, and nitroacetate undergo the palladium-catalyzed decarboxylation-allylation to afford allylated acetate, acetonitrile, and nitromethane, respectively. The mechanisms of these palladium-catalyzed decarboxylation-allylations are discussed.

    Original languageEnglish
    Pages (from-to)2988-2995
    Number of pages8
    JournalJournal of Organic Chemistry
    Volume52
    Issue number14
    Publication statusPublished - 1987

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    ASJC Scopus subject areas

    • Organic Chemistry

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