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A Glove-Box- and Schlenk-Line-Free Protocol for Solid-State C-N Cross-Coupling Reactions Using Mechanochemistry

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Title: A Glove-Box- and Schlenk-Line-Free Protocol for Solid-State C-N Cross-Coupling Reactions Using Mechanochemistry
Authors: Kubota, Koji Browse this author
Takahashi, Rikuro Browse this author
Uesugi, Minami Browse this author
Ito, Hajime Browse this author →KAKEN DB
Keywords: Mechanochemistry
Ball mill
Solid-state reactions
Issue Date: 9-Nov-2020
Publisher: American Chemical Society
Journal Title: Sustainable Chemistry & Engineering
Volume: 8
Issue: 44
Start Page: 16577
End Page: 16582
Publisher DOI: 10.1021/acssuschemeng.0c05834
Abstract: Carbon-nitrogen (C-N) bond-forming cross-coupling reactions catalyzed by palladium-based catalysts, the so-called Buchwald-Hartwig aminations, have been widely employed for the synthesis of pharmaceuticals and aryl-amine-based organic materials in academic and industrial settings. However, in solution, these reactions usually require glovebox and Schlenk line techniques, which greatly reduces their practical utility. Here, we report the development of operationally simple mechanochemical C-N cross-coupling reactions in the solid-state. Intensive investigations of various ball milling parameters revealed that the air-stable ligand tri(1-adamantyl)phosphine can be used to achieve solid-state coupling reactions between aryl halides and diarylamines with high efficiency. Notably, all experimental operations of the developed protocol can be carried out in air, thus providing a more convenient, industrially attractive, and sustainable alternative to conventional solution-based palladium-catalyzed C-N coupling reactions.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in [ACS sustainable chemistry & engineering], copyright c American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [].
Type: article (author version)
Appears in Collections:創成研究機構 (Creative Research Institution) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 久保田 浩司

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