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Kang, H. Grignard Reaction. Encyclopedia. Available online: https://encyclopedia.pub/entry/60340 (accessed on 03 October 2026).
Kang H. Grignard Reaction. Encyclopedia. Available at: https://encyclopedia.pub/entry/60340. Accessed October 03, 2026.
Kang, Helena. "Grignard Reaction" Encyclopedia, https://encyclopedia.pub/entry/60340 (accessed October 03, 2026).
Kang, H. (2026, September 23). Grignard Reaction. In Encyclopedia. https://encyclopedia.pub/entry/60340
Kang, Helena. "Grignard Reaction." Encyclopedia. Web. 23 September, 2026.
Grignard Reaction
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Organomagnesium halides (Grignard reagents, RMgX) add to polarized multiple bonds, most classically to aldehydes and ketones, to form a new carbon–carbon bond and, after hydrolysis, an alcohol. The reagent is prepared from an organic halide and magnesium metal; in solution it exists as a Schlenk equilibrium among RMgX, R2Mg, and MgX2, and the addition step is nucleophilic transfer of the organic group to the electrophilic carbon [1]. The same organomagnesium species alkylate or arylate other electrophiles, including epoxides, esters (with double addition), carbon dioxide, and activated carbon–halogen or carbon–fluorine sites on extended π systems such as fluorographene [2]. Sequential Staudinger/aza-Wittig/Grignard sequences use the addition to an in situ imine as the C–C-forming step toward iminosugars [3]. The concept is bounded as the reactivity of the C–Mg bond toward electrophiles. Transition-metal-catalyzed coupling of Grignard reagents (Kumada coupling) is a related but distinct process in which the elementary C–C bond-forming step occurs at the metal, not by direct polar addition of RMgX to a carbonyl [1].

Grignard reaction organomagnesium reagents nucleophilic addition carbon–carbon bond formation

References

  1. Raphael Mathias Peltzer; Jürgen Gauss; Odile Eisenstein; Michele Cascella; The Grignard Reaction – Unraveling a Chemical Puzzle. J. Am. Chem. Soc. 2020, 142, 2984-2994. [CrossRef]
  2. Demetrios D. Chronopoulos; Aristides Bakandritsos; Petr Lazar; Martin Pykal; Klára Čépe; Radek Zbořil; Michal Otyepka; High-Yield Alkylation and Arylation of Graphene via Grignard Reaction with Fluorographene. Chem. Mater. 2017, 29, 926-930. [CrossRef]
  3. Manuel Zoidl; Andres Gonzalez Santana; Ana Torvisco; Christina Tysoe; Aloysius Siriwardena; Stephen G. Withers; Tanja M. Wrodnigg; The Staudinger/aza-Wittig/Grignard reaction as key step for the concise synthesis of 1-C-Alkyl-iminoalditol glycomimetics. Carbohydr. Res. 2016, 429, 62-70. [CrossRef]
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Subjects: Chemistry, Organic
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Update Date: 23 Sep 2026
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