Organolithium reagent

In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation.[1] Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers. They have also been applied in asymmetric synthesis in the pharmaceutical industry.[2] Due to the large difference in electronegativity between the carbon atom and the lithium atom, the C−Li bond is highly ionic. Owing to the polar nature of the C−Li bond, organolithium reagents are good nucleophiles and strong bases. For laboratory organic synthesis, many organolithium reagents are commercially available in solution form. These reagents are highly reactive, and are sometimes pyrophoric.

Glass bottles containing butyllithium
A sec-butyllithium aggregate in which each of the four sec-butyl groups is associated with one face of the tetrahedron formed from four lithium atoms
  1. ^ Zabicky, Jacob (2009). "Analytical aspects of organolithium compounds". PATAI'S Chemistry of Functional Groups. John Wiley & Sons, Ltd. doi:10.1002/9780470682531.pat0304. ISBN 9780470682531.
  2. ^ Wu, G.; Huang, M. (2006). "Organolithium Reagents in Pharmaceutical Asymmetric Processes". Chem. Rev. 106 (7): 2596–2616. doi:10.1021/cr040694k. PMID 16836294.