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Lithiation reactions are a class of organometallic reactions where an organolithium compound is formed. This typically involves replacing a hydrogen atom in a molecule with a lithium atom. These reactions are fundamental in organic synthesis, enabling the creation of new carbon-carbon bonds and the introduction of lithium into organic molecules. The process usually requires strong bases, such as n-butyllithium or lithium diisopropylamide (LDA), to deprotonate the substrate. The choice of base and solvent is crucial, as it influences the regioselectivity and stereoselectivity of the lithiation. Common substrates for lithiation include aromatic compounds, alkenes, alkynes, and compounds with acidic alpha-hydrogens adjacent to functional groups like carbonyls or nitriles. Once the organolithium species is formed, it acts as a powerful nucleophile and can react with a wide range of electrophiles, including aldehydes, ketones, esters, alkyl halides, and carbon dioxide, to form more complex molecules. These reactions are often carried out at low temperatures to prevent side reactions and maintain the stability of the highly reactive organolithium intermediates. Lithiation is a versatile tool for functionalizing organic molecules and is widely employed in the pharmaceutical, agricultural, and materials science industries.