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Catalyzed Catalysis Using Carbophilic Lewis Acidic Gold and Lewis Basic Palladium: Synthesis of Substituted Butenolides and Isocoumarins
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    Catalyzed Catalysis Using Carbophilic Lewis Acidic Gold and Lewis Basic Palladium: Synthesis of Substituted Butenolides and Isocoumarins
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    Department of Chemistry, University of California, Irvine, California 92697-2025
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2009, 131, 50, 18022–18023
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    https://doi.org/10.1021/ja9068497
    Published November 24, 2009
    Copyright © 2009 American Chemical Society

    Abstract

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    A new strategy for gold and palladium dual-catalytic reactivity and turnover, called catalyzed catalysis, enhanced the synthetic usefulness of vinylgold intermediates by providing dual-catalytic carbon−carbon cross-coupling as an alternative to protodemetalation. This protocol enabled the synthesis of substituted butenolides and isocoumarins from allyl esters. Kinetic and spectroscopic experiments support a mechanism in which the Lewis acidic gold complex catalyzes both an initial rearrangement step and a subsequent Lewis basic palladium oxidative-addition step.

    Copyright © 2009 American Chemical Society

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    Experimental procedures, kinetic data, and compound characterization data. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Am. Chem. Soc. 2009, 131, 50, 18022–18023
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    Published November 24, 2009
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