|
|
Hokkaido University Collection of Scholarly and Academic Papers >
Graduate School of Engineering / Faculty of Engineering >
Peer-reviewed Journal Articles, etc >
Mechanochemical synthesis of magnesium-based carbon nucleophiles in air and their use in organic synthesis
| 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 |
| URI: | http://hdl.handle.net/2115/83787 |
| 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)
|
|
