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    Palladium-Catalyzed Suzuki–Miyaura Coupling of Aryl Esters
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    † Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada
    ‡ Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States
    § Department of Chemistry, Zhejiang University, Hangzhou 310027, China
    *[email protected]
    *[email protected]
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2017, 139, 3, 1311–1318
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    https://doi.org/10.1021/jacs.6b12329
    Published December 21, 2016
    Copyright © 2016 American Chemical Society
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    Abstract

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    The Suzuki–Miyaura coupling is among the most important C–C bond-forming reactions available due to its reliability, chemoselectivity, and diversity. Aryl halides and pseudohalides such as iodides, bromides, and triflates are traditionally used as the electrophilic coupling partner. The expansion of the reaction scope to nontraditional electrophiles is an ongoing challenge to enable an even greater number of useful products to be made from simple starting materials. Herein, we present how an NHC-based Pd catalyst can enable Suzuki–Miyaura coupling where the C(acyl)–O bond of aryl esters takes on the role of electrophile, allowing the synthesis of various ketone-containing products. This contrasts known reactions of similar esters that provide biaryls via nickel catalysis. The underlying cause of this mechanistic divergence is investigated by DFT calculations, and the robustness of esters compared to more electrophilic acylative coupling partners is analyzed.

    Copyright © 2016 American Chemical Society

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    Cite this: J. Am. Chem. Soc. 2017, 139, 3, 1311–1318
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