What are Organolithium Compounds?

Organolithium compounds (RLi) are organometallic compounds that contain carbon – lithium bonds. Unlike Grignard reagents which inserts between the carbon and halide bond, Lithium replaces the halide to form organolithium, forming a stronger partial negative charge on the carbon.

Organolithium reagents act as good “nucleophilic carbons” and strong bases that exploit non-polar bonds of hydrocarbons to produce conjugate bases able to deprotonate many compounds. This includes extremely weak acids such as alcohols and amines.

Organolithium compounds are:

• Strong bases and nucleophiles
• Reagents for
• Initiators for anionic polymerization
• Able to provide transmetallate reagents in catalysts, and carbon-based ligands

Benefits and Limitations of Organolithium Compounds

These compounds have many beneficial properties, including:

• Good solubility in organic solvents
• Enhanced stability, effectiveness, and aggressiveness compared to lithium amides (LDA) and Grignard reagents (RMgX), with the ability to be safety prepared, stored, and transported
• Many organolithium compounds are commercially available
• Organolithium compounds are corrosive, flammable, and pyrophoric. They ignite spontaneously when exposed to air or humidity. Proper precautions are needed when using them.