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Preparation of Dienyl Boronates by Tandem Ene–Yne Metathesis/Dienyl Isomerization: Ready Access to Diene Building Blocks for the Synthesis of Polyenes

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    Preparation of Dienyl Boronates by Tandem Ene–Yne Metathesis/Dienyl Isomerization: Ready Access to Diene Building Blocks for the Synthesis of Polyenes
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2022, 87, 21, 14078–14092
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    https://doi.org/10.1021/acs.joc.2c01678
    Published October 12, 2022
    Copyright © 2022 American Chemical Society
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    Abstract

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    The ene–yne metathesis of alkenyl boronates with terminal alkynes is reported. These challenging metatheses were accomplished using a Grubbs catalyst bearing the cyclic alkyl amino carbene (CAAC) ligand, whereas N-heterocyclic carbene (NHC) derived catalysts gave lower yields. Subsequent dienyl isomerization via a cobalt-catalyzed hydrogen atom transfer (HAT) furnished the more substituted dienyl boronate with high EE/EZ ratios. Finally, the resulting dienyl boronate products were successfully used in Suzuki–Miyaura cross-coupling reactions and in a Diels–Alder cycloaddition.

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    Supporting Information

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    • FAIR data, including the primary NMR FID files, for compounds 1b, 1c, 3aa, 3ab, 3bb–3bl, 3cd, 3cf, 3cg, 3ck, 4ba, 4bb, 4bd, 4bf–4bl, 5–13 (ZIP)

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2022, 87, 21, 14078–14092
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.2c01678
    Published October 12, 2022
    Copyright © 2022 American Chemical Society
    Request reuse permissions

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