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Palladium-Catalyzed Arylation of α-Methylene-γ-butyrolactone:  3-Benzylfuran-2(5H)-ones vs (Z)-Benzylidene-γ-butyrolactones and Their Reduction to 3-Benzyl-γ-butyrolactones
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    Palladium-Catalyzed Arylation of α-Methylene-γ-butyrolactone:  3-Benzylfuran-2(5H)-ones vs (Z)-Benzylidene-γ-butyrolactones and Their Reduction to 3-Benzyl-γ-butyrolactones
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    Dipartimento di Chimica, Ingegneria Chimica e Materiali, Via Vetoio, 67010 Coppito Due (AQ) Italy, Department of Biochemistry, University Medical School, H-7643 Pécs, P.O. Box 99, Hungary, and Janus Pannonius University, Department of Inorganic Chemistry and Research Group for Chemical Sensors of the Hungarian Academy of Sciences, H-7624 Pécs, ifjùsàg u.6. Hungary
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    Organic Letters

    Cite this: Org. Lett. 2000, 2, 1, 69–72
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    https://doi.org/10.1021/ol9912130
    Published December 17, 1999
    Copyright © 2000 American Chemical Society

    Abstract

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    The palladium-catalyzed arylation of the α-methylene-γ-butyrolactone proceeds in good yields and may be directed toward the synthesis of 3-benzylfuran-2(5H)-ones when the starting aryl iodides contain strongly electron-withdrawing groups. The combined palladium-catalyzed arylation/hydrogenation of the α-methylene-γ-butyrolactone represents a new simple entry into functionalized α-benzyl-γ-butyrolactones.

    Copyright © 2000 American Chemical Society

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     Ingegneria Chimica e Materiali.

     University Medical School.

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     Janus Pannonius University.

    Cited By

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    33. . Preparation of Alkyls, Methylenes and Aryls. 2003, 115-225. https://doi.org/10.1002/9780471476665.ch5
    34. Antonio Arcadi, Marco Chiarini, Fabio Marinelli, Zoltan Berente, Laszlo Kollar. ChemInform Abstract: Palladium‐Catalyzed Arylation of α‐Methylene‐γ‐butyrolactone: 3‐Benzylfuran‐2(5H)‐ones vs (Z)‐Benzylidene‐γ‐butyrolactones and Their Reduction to 3‐Benzyl‐γ‐butyrolactones.. ChemInform 2000, 31 (15) https://doi.org/10.1002/chin.200015105

    Organic Letters

    Cite this: Org. Lett. 2000, 2, 1, 69–72
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol9912130
    Published December 17, 1999
    Copyright © 2000 American Chemical Society

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