Lithium acetylide ethylenediamine complex is used in the synthesis of a chiral cyclopropanol. It is also used as an alkynylating reagent for the enantioselective alkynylation of ketones catalyzed by lithium binaphtholate without using other metal sources.
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Applications
Lithium acetylide ethylenediamine complex is used in the synthesis of a chiral cyclopropanol. It is also used as an alkynylating reagent for the enantioselective alkynylation of ketones catalyzed by lithium binaphtholate without using other metal sources.
Solubility
Soluble in ethylene diamine, n-propyl amine, n-butyl amine, pyridine, dimethyl formamaide, diglyme, dioxan and dimethylsulfoxide.
Notes
Moisture and light sensitive. Store in cool place. Incompatible with alcohols, acids, oxidizing agents, water. It reacts with water to form lithium hydroxide and acetylene, which is a flammable gas. Over time, pressure may increase causing containers to burst. Handle and open container with care.
RUO – Research Use Only
Convenient, relatively stable form of lithium acetylide, soluble in organic solvents such as DMF, DMSO, diglyme and dioxan: J. Org. Chem., 28, 2775 (1963); 29, 1872 (1964). For addition to ketones to give ethynyl carbinols, see: J. Org. Chem., 30, 1604 (1965). For reaction with alkyl halides in DMSO to give terminal alkynes, see: Can. J. Chem., 41, 2600 (1963).
Hashimoto, K.; Kumagai, N.; Shibasaki, M. A Carbon Nanotube Confinement Strategy to Implement Homogeneous Asymmetric Catalysis in the Solid Phase. Chem. Eur. J. 2015, 21 (11), 4262-4266.
Bassan, E. M.; Baxter, C. A.; Beutner, G. L.; Emerson, K. M.; Fleitz, F. J.; Johnson, S.; Keen, .; Kim, M. M.; Kuethe, J. T.; Leonard, W. R.; Mullens, P. R.; Muzzio, D. J.; Roberge, C.; Yasuda, N. Multikilogram-Scale Synthesis of a Chiral Cyclopropanol and an Investigation of the Safe Use of Lithium Acetylide-Ethylene Diamine Complex. Org. Process Res. Dev. 2011, 16 (1), 87-95.