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Gilman reagent

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A Gilman reagent is a lithium and copper (diorganocopper) reagent compound, R₂CuLi, where R is an organic radical. These are useful because they react with chlorides, bromides, and iodides to replace the halide group with an R group. This is extremely useful in creating larger molecules from smaller ones.

These reagents were discovered by Henry Gilman. Lithium dimethylcopper (CH₃)₂CuLi can be prepared by adding copper(I) iodide to methyl lithium in tetrahydrofuran at -78°C. In the reaction depicted below,^[1] the Gilman reagent is a methylating reagent reacting with an alkyne in an conjugate addition, and the negative charge is trapped in a nucleophilic acyl substitution with the ester group forming a cyclic enone.

References

^ Modern Organocopper Chemistry, N. Krause Ed. Wiley-VCH, 2002.

v • d • e Concepts in organometallic chemistry
Principles	Electron counting, 18-Electron rule, Polyhedral skeletal electron pair theory, Isolobal principle, π backbonding, Hapticity
Reactions	Oxidative addition, Reductive elimination, Beta-hydride elimination, Transmetalation, Carbometalation
Types of compounds	Gilman reagent, Grignard reagents, Cyclopentadienyl complexes, Metallocenes, Sandwich compound, Transition metal carbene complexes
Applications	Monsanto process, Ziegler-Natta catalyst, Olefin metathesis
Related branches of chemistry	Organic chemistry - Inorganic chemistry - Bioinorganic chemistry