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

Koji Kubota (), Tamae Seo, Katsumasa Koide, Yasuchika Hasegawa and Hajime Ito ()
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Koji Kubota: Hokkaido University
Tamae Seo: Hokkaido University
Katsumasa Koide: Hokkaido University
Yasuchika Hasegawa: Hokkaido University
Hajime Ito: Hokkaido University

Nature Communications, 2019, vol. 10, issue 1, 1-11

Abstract: 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.

Date: 2019
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DOI: 10.1038/s41467-018-08017-9

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