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Organocuprate reagent or the Gilman reagent (R)₂CuLi is formed when the organolithium compound (RLi) is reacted with copper iodide (Cul) in the presence of a solvent like THF shown as below:

Gilman reagent carries two alkyl groups (R), and a copper metal along with a lithium atom attached to it.

Organocuprate reactions keep varying with the type of alkyl halide (RX) and organocuprate (RCuLi) used. Organocuprate reagent shows coupling reacting as they work well with sp² hybrid substrates such as vinyl halide and aryl halides.

The product formed when Organocuprate reagent reacts with aryl halide is given below.

Here, the new carbon-carbon bond is shown in bold.

When vinyl halides react with Organocuprate reagent, it preserves its stereochemistry.

Formation of (Z)-hex-1-enylbenxzene

Here also the new carbon-carbon bonds are shown in bold the stereochemistry of the reactant is retained in the product (Stereospecific reaction).