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.
By Qinling Li


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