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

    研究成果: Article査読

    111 被引用数 (Scopus)

    抄録

    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.

    本文言語English
    ページ(範囲)2988-2995
    ページ数8
    ジャーナルJournal of Organic Chemistry
    52
    14
    出版ステータスPublished - 1987

    ASJC Scopus subject areas

    • Organic Chemistry

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