Editing Grignard reaction (section)

==Variants==
Other variations of the Grignard reagent have been discovered to improve the chemoselectivity of the Grignard reaction, which include but are not limited to: Turbo-Grignards, organocerium reagents, and organocuprate (Gilman) reagents.

===Turbo-Grignards===
Turbo-Grignards are Grignard reagents modified with [[lithium chloride]]. Compared to conventional Grignard reagents, Turbo-Grignards are more [[chemoselectivity|chemoselective]]; [[ester]]s, [[amide]]s, and [[nitrile]]s do not react with the Turbo-Grignard reagent.<ref>{{cite journal |doi=10.1002/anie.202302489 |title=Comprehensive Study of the Enhanced Reactivity of Turbo-Grignard Reagents* |date=2023 |last1=Hermann |first1=Andreas |last2=Seymen |first2=Rana |last3=Brieger |first3=Lukas |last4=Kleinheider |first4=Johannes |last5=Grabe |first5=Bastian |last6=Hiller |first6=Wolf |last7=Strohmann |first7=Carsten |journal=Angewandte Chemie International Edition |volume=62 |issue=25 |pages=e202302489 |s2cid=257765567 |doi-access=free |pmid=36971042 }}</ref>
[[File:Turbo-Grignard_formation.png|none|thumb|320x320px|An example reaction of forming a Turbo-Grignard with an ester group.]]

===Heterometal-modified Grignard reagents===
[[File:Cuprate_conjugate_addition_with_lewis_acid.png|none|thumb|405x405px|A conjugated 1,4 addition using a Gilman reagent with an arbitrary R group]]
The behavior of Grignard reagents can be usefully modified in the present of other metals.  Copper(I) salts give
[[Gilman reagent|organocuprates]] that preferentially effect [[nucleophilic conjugate addition|1,4 addition]].<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>  Cerium trichloride allows selective 1,2-additions to the same substrates.  Nickel and palladium halides catalyze [[cross coupling reaction]]s.