Editing Gilman reagent (section)

==Use in organic chemistry==
[[File:Cuprate_conjugate_addition_with_lewis_acid.png|none|thumb|305x305px|A conjugated 1,4 addition using a Gilman reagent with an arbitrary R group]]

These reagents are useful because, unlike related [[Grignard reagent]]s and [[organolithium reagent]]s, they react with [[Organic halide|organic]] [[halide]]s to replace the [[halides|halide]] group with an R group (the [[Corey–House synthesis|Corey–House reaction]]).  Such displacement reactions allow for the synthesis of complex products from simple building blocks.<ref>{{cite journal | title = Organocopper(I) Compounds and Organocuprates in Synthesis| journal = Synthesis  | author = J. F. Normant| pages = 63–80| doi = 10.1055/s-1972-21833| volume = 1972 | issue = 2| year = 1972}}</ref><ref name=":4">{{Cite journal |last=Woodward |first=Simon |date=2000-01-01 |title=Decoding the 'black box' reactivity that is organocuprate conjugate addition chemistry |url=https://pubs.rsc.org/en/content/articlelanding/2000/cs/b002690p |journal=Chemical Society Reviews |language=en |volume=29 |issue=6 |pages=393–401 |doi=10.1039/B002690P |issn=1460-4744|url-access=subscription }}</ref> [[Lewis acids and bases|Lewis acids]] can be used to modify the reagent.<ref name=":4" /> 


{{Image frame|content=<math chem>
[\ce{R}{-}{\color{Blue}\ce{Cu}}\ce{-R}]^-\ce{Li+}\ 
\xrightarrow{\color{Red}\ce{R'-X}}\ 
\overbrace{\left[\ce R{-}\overset{{\displaystyle \color{Red} \ce R'} \atop |}\underset{| \atop {\displaystyle \color{Red} \ce X}}{\color{Blue}\ce{Cu}}\ce{-R} \right]^-\ce{Li+}}^\text{planar intermediate} 
\ce{-> R}{-}{\color{Blue}\ce{Cu}} + \ce{R}{-}{\color{Red}\ce{R'}} + \ce{Li}{-}{\color{Red}\ce{X}}
</math>|align=center|width=540|caption=Generalized [[chemical reaction]] showing '''Gilman’s reagent''' reacting with [[organic halide]] to form products and showing Cu(III) [[reaction intermediate]]}}