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A Gilman Reagent is an organometallic reagent containing two R-groups (alkyl or aryl), copper, and lithium. The general formula of Gilman reagents can be expressed as R2CuLi. Unlike Grignard reagents, these compounds tend to replace the halide group with an R group when reacted with organic halides.

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A Gilman reagent is an organocopper compound with the formula Li[CuR2], where R is an alkyl or aryl. It is a colorless solid that is used in the Gilman reaction. 

Here are some things to know about Gilman reagents: 

Discovery

American chemist Henry Gilman discovered Gilman reagents in 1952. 

Preparation

Gilman reagents are prepared by reacting two equivalents of alkyl or aryl lithium with one equivalent of copper salt in the presence of diethyl ether or TMS as a solvent. 

Structure

Gilman reagents are typically illustrated by a C-Cu-C core with a lithium counterion. 

Applications

Gilman reagents are used in the Corey-House reaction and for synthesizing relatively complex products from simple blocks. 

Reactivity

The carbon–copper bond in Gilman reagents is less polarized than the carbon–magnesium bond.

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