Editing Organolithium reagent (section)

{{short description|Chemical compounds containing C–Li bonds}}

In [[organometallic chemistry]], '''organolithium reagents''' are [[chemical compound]]s that contain [[carbon]]–[[lithium]] (C–Li) [[Chemical bond|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]].<ref name=analytical>
{{cite book| last = Zabicky | first = Jacob | chapter = Analytical aspects of organolithium compounds| title = PATAI'S Chemistry of Functional Groups.| publisher = John Wiley & Sons, Ltd | year = 2009| isbn = 9780470682531 | doi =  10.1002/9780470682531.pat0304}}</ref> 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.<ref name=orglipharm>
{{cite journal| title = Organolithium Reagents in Pharmaceutical Asymmetric Processes| author = Wu, G.
|author2=Huang, M.| journal = Chem. Rev.| year = 2006| volume = 106| issue = 7
| pages = 2596–2616| doi = 10.1021/cr040694k| pmid=16836294}}</ref> Due to the large difference in [[electronegativity]] between the carbon atom and the lithium atom, the C−Li bond is highly [[ionization|ionic]]. Owing to the polar nature of the C−Li bond, organolithium reagents are good [[nucleophile]]s and strong bases. For laboratory organic synthesis, many organolithium reagents are commercially available in solution form. These reagents are highly reactive, and are sometimes [[pyrophoricity|pyrophoric]]. [[File:Glasbottles containing Butyllithium, Buli.jpg|thumb|right|Glass bottles containing butyllithium]]
[[File:Sec-butyllithium-2D-skeletal.png|thumb|right|230px|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]]