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Mechanochemical synthesis of magnesium-based carbon nucleophiles in air and their use in organic synthesis

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Title: Mechanochemical synthesis of magnesium-based carbon nucleophiles in air and their use in organic synthesis
Authors: Takahashi, Rina Browse this author
Hu, Anqi Browse this author
Gao, Pan Browse this author
Gao, Yunpeng Browse this author
Pang, Yadong Browse this author
Seo, Tamae Browse this author
Jiang, Julong Browse this author
Maeda, Satoshi Browse this author
Takaya, Hikaru Browse this author
Kubota, Koji Browse this author
Ito, Hajime Browse this author →KAKEN DB
Issue Date: 18-Nov-2021
Publisher: Nature Portfolio
Journal Title: Nature communications
Volume: 12
Issue: 1
Start Page: 6691
Publisher DOI: 10.1038/s41467-021-26962-w
Abstract: Since the discovery of Grignard reagents in 1900, the nucleophilic addition of magnesium-based carbon nucleophiles to various electrophiles has become one of the most powerful, versatile, and well-established methods for the formation of carbon-carbon bonds in organic synthesis. Grignard reagents are typically prepared via reactions between organic halides and magnesium metal in a solvent. However, this method usually requires the use of dry organic solvents, long reaction times, strict control of the reaction temperature, and inert-gas-line techniques. Despite the utility of Grignard reagents, these requirements still represent major drawbacks from both an environmental and an economic perspective, and often cause reproducibility problems. Here, we report the general mechanochemical synthesis of magnesium-based carbon nucleophiles (Grignard reagents in paste form) in air using a ball milling technique. These nucleophiles can be used directly for one-pot nucleophilic addition reactions with various electrophiles and nickel-catalyzed cross-coupling reactions under solvent-free conditions. Grignard reagents have widespread utility in organic chemistry, but their preparation is limited by several drawbacks, such as the use of dry organic solvents and long reaction times. Here, the authors report a general mechanochemical synthesis of Grignard reagents in paste form in air, using a ball milling technique.
Type: article
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

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