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In 2001, Harrowfield and co-workers first attempted mechanochemical reactions of 1-chloro- or 1-bromo-naphthalenes with magnesium metal in a glovebox 25. In this context, the use of ball milling techniques 16, 17, 18, 19, 20, 21, 22, 23, 24 for the solvent-free preparation of Grignard reagents via reactions between aryl halides and magnesium metal has been studied by several research groups (Fig. Unfortunately, these requirements still represent major drawbacks from both an environmental and an economic perspective, and often cause reproducibility problems for unreactive organic halides. Moreover, the surface of the magnesium metal may be covered with an unreactive oxide layer 10, which requires a pre-activation process involving heating, ultrasound 11, or microwave 12 treatment, and/or the addition of activating reagents 13, 14, 15. 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.
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The direct insertion of magnesium metal into organic halides is one of the most established routes, as it is an atom-economical process with low toxicity (Fig. Thus, the development of efficient methods for their preparation has attracted considerable interest 6, 7, 8. Since then, Grignard reagents have occupied an important place in organic chemistry, as they have been used to produce numerous synthetic intermediates and valuable functional molecules in the materials, pharmaceutical, food, polymer, and related chemical industries 2, 3, 4, 5. The discovery of what later became commonly known as the ‘Grignard reagents’ and their use as carbon nucleophiles were first reported in 1900 by Victor Grignard 1. 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. Here, we report the general mechanochemical synthesis of magnesium-based carbon nucleophiles (Grignard reagents in paste form) in air using a ball milling technique. 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. Grignard reagents are typically prepared via reactions between organic halides and magnesium metal in a solvent. 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.