Organolithium reagent

An organolithium reagent contains a carbon–lithium bond. Its strongly polarized bond makes it a powerful base and nucleophile in organic synthesis.

Carbon–lithium bond: A covalent bond between carbon and lithium, strongly polarized toward carbon. Its polarization gives organolithium compounds their carbanion-like reactivity.
Nucleophilic addition to carbonyls: Addition of an electron-rich nucleophile to the electrophilic carbon of a carbonyl group. Organolithium reagents add to aldehydes and ketones, forming carbon–carbon bonds.
Organometallic chemistry: The study of compounds containing bonds between carbon and metals. Organolithium reagents are among the most reactive and widely used organometallic compounds.
Wilhelm Schlenk: A German chemist known for foundational research on organometallic compounds and air-sensitive techniques. His work on organometallic equilibria helped establish the chemistry surrounding organolithium reagents.
Organolithium aggregation: The association of organolithium molecules into dimers, tetramers, or larger structures. Aggregation changes reagent structure and can alter reaction rates and selectivity.
Lithiation: The replacement of a hydrogen or other substituent by lithium in a molecule. Organolithium reagents enable lithiation that creates reactive intermediates for synthesis.
Lithium: A soft, highly reactive alkali metal with atomic number 3. Lithium’s electropositive character contributes to the polarized carbon–lithium bond.
Georg Wittig: A German chemist whose work transformed synthetic organic chemistry, including the chemistry of organolithium compounds. Wittig’s organolithium-based methods demonstrated the reagents’ power in constructing organic molecules.
Lithium–halogen exchange: A reaction that replaces a carbon-bound halogen with lithium using an organolithium reagent. It is a common route for generating organolithium reagents from organic halides.
Metalation: The formation of a carbon–metal bond by replacing a carbon-bound hydrogen or other group. Organolithium bases are widely used to metalate otherwise unreactive carbon positions.

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