Gilman reagent

What is Gilman reagent?

The Gilman reagent, also known as the lithium dialkylcuprate, R1R2CuLi is prepared by combining an alkyl lithium reagent with copper(I) iodide. Despite its tendency towards instability, this reagent can engage in organometallic coupling reactions with alkyl bromides and iodides.

In contrast to other reagents like Grignard reagents and organolithium reagents, the Gilman reagent’s unique reactivity is due to its diorganocopper structure with the formula R1R2CuLi, where R1 and R2 represents an alkyl or aryl group. This property allows for displacement reactions with organic halides, such as the Corey-House reaction, where the halide group is substituted with an R group, leading to the synthesis of complex products from simple starting materials.

References

The Preparation of Methylcopper and some Observations on the Decomposition of Organocopper Compounds
Henry Gilman, Reuben G. Jones, and L. A. Woods
The Journal of Organic Chemistry 1952 17 (12), 1630-1634
DOI: 10.1021/jo50012a009

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