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.