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On the Nature of the Oxidative Heterocoupling of Lithium Enolates

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    On the Nature of the Oxidative Heterocoupling of Lithium Enolates
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    Department of Chemistry, Lehigh University, Bethlehem, Pennsylvania 18015, United States
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2011, 133, 30, 11492–11495
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    https://doi.org/10.1021/ja205017e
    Published June 30, 2011
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    Abstract

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    The coupling of enolates through single-electron oxidation is one of the most direct routes for generating 1,4-dicarbonyls. Recent work on the intermolecular heterocoupling of equimolar amounts of two different enolates through single-electron oxidation has shown that synthetically useful yields beyond those predicted by statistics can be obtained. To determine the underlying basis for the selective formation of heterocoupled products, kinetic, 7Li NMR, and synthetic studies were performed. The collection of data obtained from these experiments shows that the selective formation of heterocoupled products is a consequence of heteroaggregation of lithium enolates.

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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2011, 133, 30, 11492–11495
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja205017e
    Published June 30, 2011
    Copyright © 2011 American Chemical Society
    Request reuse permissions

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