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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.
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.
Hazard Statements: H261-H314-H318
In contact with water releases flammable gas. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P280-P305+P351+P338-P310a-P370+P378i-P403-P402+P404
Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. In case of fire: Use for extinction: Fire-extinguishing powder. Store in a well-ventilated place. Store in a dry place. Store in a closed container.