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

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.

SUBMITTER: Kubota K

PROVIDER: S-EPMC6328594 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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

Kubota Koji K Seo Tamae T Koide Katsumasa K Hasegawa Yasuchika Y Ito Hajime H

Nature communications 20190110 1

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 ...[more]

PMID: 30631071

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