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Organometallic bromides are synthesized by treating an alkyl or aryl bromide with a metal, such as lithium, magnesium, or zinc. The reactivity of these compounds varies based on the reduction potential of the metal. The reactions involving organometallic bromides are very sensitive - requiring inert atmosphere and dry solvents. The organo magnesium halides are generally referred to as Grignard reagents. The metal-carbon bond in alkyl magnesium bromides has a significant amount of ionic character.
Alkyl magnesium bromide is considered to be a hybrid of ionic and covalent Lewis structures. Alkyl magnesium bromides are sources of nucleophiles which attack the positive end of the C=O double bond. With appropriate carbonyl compounds they produce primary, secondary, and tertiary alcohols; and carboxylic acid. They add to epoxides to form carbon-carbon bonds by attacking the less substituted end of the epoxide. Organomanganese bromides, behaving like soft Grignard reagents, readily react with carbonyl compounds like aldehydes, ketones, carbon dioxide, and isocyanates, but not with esters, nitriles, or amides. The organozinc halides are used in cross-coupling reactions (known as the Negishi cross-coupling reaction), which involve the coupling of organic halides with organozinc halides, forming carbon-carbon bonds in the process. A palladium (0) species is used as the metal catalyst. For a review of organonickel reagents, see: Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.; Garg, N. K.; Percec, V. Nickel-Catalyzed Cross-Couplings Involving Carbon-Oxygen Bonds, Chem. Rev., 2011, 111 (3), 1346-1416.