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Regioselective Synthesis and Slow-Release Suzuki–Miyaura Cross-Coupling of MIDA Boronate-Functionalized Isoxazoles and Triazoles

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    Regioselective Synthesis and Slow-Release Suzuki–Miyaura Cross-Coupling of MIDA Boronate-Functionalized Isoxazoles and Triazoles
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    Novartis Institutes for BioMedical Research, Inc., 250 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States
    E-mail: [email protected]
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2011, 76, 24, 10241–10248
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    https://doi.org/10.1021/jo201973t
    Published November 2, 2011
    Copyright © 2011 American Chemical Society
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    Abstract

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    The efficient preparation of heterocycles with a range of substitutions ortho to heteroatoms remains as a challenge in organic synthesis, particularly relevant to the construction of druglike molecules due to the ubiquitous presence of such moieties in that chemical space. Modular installation of heterocyclic building blocks using Suzuki–Miyaura cross-coupling is a conceptually useful strategy to address this challenge, though this has historically been met with technical difficulty due to issues of inaccessibility and instability of the requisite heterocyclic boronates. Herein we report a mild and highly regioselective cycloaddition approach which affords convenient access to stable MIDA boronate-functionalized isoxazoles and triazoles and their subsequent efficient Suzuki–Miyaura cross-coupling. This methodology is then further applied to a set of druglike compounds in an efficient one-pot telescoped sequence in line with green chemistry principles.

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    Cite this: J. Org. Chem. 2011, 76, 24, 10241–10248
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    https://doi.org/10.1021/jo201973t
    Published November 2, 2011
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