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Olefin-accelerated solid-state C–N cross-coupling reactions using mechanochemistry

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  • Koji Kubota

    (Hokkaido University)

  • Tamae Seo

    (Hokkaido University)

  • Katsumasa Koide

    (Hokkaido University)

  • Yasuchika Hasegawa

    (Hokkaido University
    Hokkaido University)

  • Hajime Ito

    (Hokkaido University
    Hokkaido University)

Abstract

Palladium-catalyzed cross-coupling reactions are one of the most powerful and versatile methods to synthesize a wide range of complex functionalized molecules. However, the development of solid-state cross-coupling reactions remains extremely limited. Here, we report a rational strategy that provides a general entry to palladium-catalyzed Buchwald-Hartwig cross-coupling reactions in the solid state. The key finding of this study is that olefin additives can act as efficient molecular dispersants for the palladium-based catalyst in solid-state media to facilitate the challenging solid-state cross-coupling. Beyond the immediate utility of this protocol, our strategy could inspire the development of industrially attractive solvent-free palladium-catalyzed cross-coupling processes for other valuable synthetic targets.

Suggested Citation

  • Koji Kubota & Tamae Seo & Katsumasa Koide & Yasuchika Hasegawa & Hajime Ito, 2019. "Olefin-accelerated solid-state C–N cross-coupling reactions using mechanochemistry," Nature Communications, Nature, vol. 10(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-018-08017-9
    DOI: 10.1038/s41467-018-08017-9
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