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Organozinc iodides, organocopper iodides, organomagnesium iodides, and organomanganese iodides are some of the more popularly known organometallic iodides. Organometallic iodides participate in many important organic transformations, which include Grignard reactions, Simmons-smith reaction, Barbier reaction, and Fukuyama coupling.
Simmons-Smith reagent, namely iodomethylzinc iodide (IZnCH2I), like a carbene equivalent, is used for stereospecific cyclopropanation of alkenes. Grignard reagents (RMgI) are widely used in synthetic organic chemistry for the formation of a variety of C-C bonds. Being strongly nucleophilic, they readily react with carbonyl compounds leading to the formation of a wide range of organic compounds such as aldehydes, ketones, and alcohols. Organomanganese iodides (RMnI) behave like soft Grignard reagents, and react with aldehydes, ketones, carbon dioxide, and isocyanates. However, they resist reacting with esters, nitriles, or amides. In the Fukuyama coupling, organozinc iodides react with thioester derivatives in the presence of a palladium catalyst to yield ketonic compounds. Organometallic iodides such as organozinc iodides have been used in the synthesis of biotin through Fukuyama coupling. Organozinc iodides take part in Negishi coupling, which is often used in the synthesis of natural products. 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.