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Synfacts 2022; 18(02): 0151
DOI: 10.1055/s-0041-1737790
Metals in Synthesis

Like a Rolling Stone! Mechanochemical Synthesis of Grignard Reagents in Air

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Benedikt Wolff
Takahashi R, Hu A, Gao P, Gao Y, Pang Y, Seo T, Jiang J, Maeda S, Takaya H, Kubota K, *, Ito H. * Hokkaido University, Sapporo, Japan
Mechanochemical Synthesis of Magnesium-Based Carbon Nucleophiles in Air and Their Use in Organic Synthesis.

Nat. Commun. 2021;
12
DOI: 10.1038/s41467-021-26962-w.
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Key words

ball mill - carbon nucleophiles - Grignard reagents - mechanochemical synthesis

Significance

A mechanochemical approach for the generation of Grignard reagents using a ball mill is presented. The solvent-free, in-air generation of these carbon nucleophiles and their nucleophilic addition to electrophiles opens a straight­forward way to conduct a classic reaction. This method can also be applied to Kumada–Tamao–Corriu couplings and copper-catalyzed conjugate additions.


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Comment

Addition of various mechanochemically prepared Grignard regents to aldehydes or ketones gives the corresponding alcohols in good to excellent yield. Even solid arylbromides with low solubility can be transformed into the corresponding Grignard reagents where the classic approach fails. Only 3.0–6.0 equivalents of a coordinating ether solvent are required for the reaction to occur.


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Publication History

Article published online:
18 January 2022

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