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Ni(COD)2/PCy3 Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates in THF at Room Temperature

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    Ni(COD)2/PCy3 Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates in THF at Room Temperature
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    Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States
    E-mail: [email protected]
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2011, 76, 24, 9946–9955
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    https://doi.org/10.1021/jo202037x
    Published November 7, 2011
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    Abstract

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    Reaction conditions for the Ni(COD)2/PCy3 catalyzed cross-coupling of aryl neopentylglycolboronates with aryl mesylates were developed. By using optimized reaction conditions, Ni(COD)2/PCy3 was shown to be a versatile catalyst for the cross-coupling of a diversity of aryl neopentylglycolboronates with aryl and heteroaryl mesylates and sulfamates containing both electron-donating and electron-withdrawing substituents in their para, ortho, and meta positions in THF at room temperature. This Ni-catalyzed cross-coupling of aryl neopentylglycolboronates is also effective for the synthesis of heterobiaryls and biaryls containing electrophilic functionalities sensitive to organolithium and organomagnesium derivatives. In combination with the recently developed Ni-catalyzed neopentylglycolborylation, all Ni-catalyzed routes to functional biaryls and heterobiaryls are now easily accessible.

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    1H NMR, 13C NMR, and HRMS for all new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Org. Chem. 2011, 76, 24, 9946–9955
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    https://doi.org/10.1021/jo202037x
    Published November 7, 2011
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