open access

https://hdl.handle.net/2115/93010

Dual Nickel(II)/Mechanoredox Catalysis: Mechanical-Force-Driven Aryl-Amination Reactions Using Ball Milling and Piezoelectric Materials

英語

Mechanoredox

2023-10-16

Wiley-Blackwell

Angewandte chemie-international edition

62(42)

e202311531

The combination of a nickel(II) catalyst and a mechanoredox catalyst under ball-milling conditions promotes mechanical-force-driven C-N cross-coupling reactions. In this nickel(II)/mechanoredox cocatalyst system, the modulation of the oxidation state of the nickel center, induced by piezoelectricity, is used to facilitate a highly efficient aryl-amination reaction, which is characterized by a broad substrate scope, an inexpensive combination of catalysts (NiBr2 and BaTiO3), short reaction times, and an almost negligible quantity of solvents. Moreover, this reaction can be readily up-scaled to the multi-gram scale, and all synthetic operations can be carried out under atmospheric conditions without the need for complicated reaction setups. Furthermore, this force-induced system is suitable for excitation-energy-accepting molecules and poorly soluble polyaromatic substrates that are incompatible with solution-based nickel(II)/photoredox cocatalysts. We have developed a new class of synergistic catalytic system that uses a nickel(II) catalyst and a mechanoredox catalyst to promote mechanochemical-force-driven C-N cross-coupling reactions. This reaction shows a broad substrate scope, an inexpensive catalyst, short reaction time, and an almost negligible quantity of solvents. The present approach accordingly complements existing nickel(II)/photoredox cocatalysis.

学術雑誌論文

Accepted Manuscript

This is the peer reviewed version of the following article: Seo, T., Kubota, K., Ito, H., Angew. Chem. Int. Ed. 2023, 62, e202311531, which has been published in final form at https://doi.org/10.1002/anie.202311531. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.

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