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Mechanochemically Generated Calcium-Based Heavy Grignard Reagents and Their Application to Carbon-Carbon Bond-Forming Reactions

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Title: Mechanochemically Generated Calcium-Based Heavy Grignard Reagents and Their Application to Carbon-Carbon Bond-Forming Reactions
Authors: Gao, Pan Browse this author
Jiang, Julong Browse this author
Maeda, Satoshi Browse this author →KAKEN DB
Kubota, Koji Browse this author
Ito, Hajime Browse this author →KAKEN DB
Keywords: Ball Mill
Cross-Electrophile Coupling
Solid-State Reaction
Issue Date: 10-Oct-2022
Publisher: Wiley-Blackwell
Journal Title: Angewandte chemie-international edition
Volume: 61
Issue: 41
Start Page: e202207118
Publisher DOI: 10.1002/anie.202207118
Abstract: In sharp contrast to the use of conventional magnesium-based Grignard reagents (R-MgX), the application of calcium-based heavy Grignard reagents (R-CaX) in organic synthesis remains poorly explored. This is mainly due to the lack of experimentally simple ways to access such organocalcium nucleophiles from readily available starting materials under mild conditions. Here, we show that a mechanochemical technique using ball milling allows the generation of calcium-based heavy Grignard reagents from aryl halides and commercially available calcium metal without complicated pre-activation processes. Notably, all experimental operations can be carried out in air. Our operationally simple protocol enables the rapid development of novel cross-electrophile-coupling reactions mediated by arylcalcium nucleophiles, which are rather difficult using conventional Grignard reagents. This method will allow synthetic chemists to readily access the novel and unique reactivity of organocalcium nucleophiles.
Rights: This is the peer reviewed version of the following article: [FULL CITE], which has been published in final form at 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.
Type: article (author version)
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)

Submitter: 久保田 浩司

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