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Updated: Aug 14, 2026
A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
Gas-phase reactions of lithium dimethylaminoborohydride and related species
Lawrence M Pratt1, Ngân Van Nguyên
1Department of Chemistry, Fisk University, 1000 17th Avenue North, Nashville, Tennessee 37209, USA. lpratt@fisk.edu
Abstract:
[reaction: see text] Ab initio and density functional theory (DFT) calculations were used to examine the mechanisms of reduction and amination of chloromethane by lithium dimethylaminoborohydride (LAB) in the gas phase. For comparison, the amination of chloromethane by lithium dimethylamide and the reduction by borane, diborane, and borohydride ions were also examined. The reduction of chloromethane by LAB occurred most readily from a conformation that allowed coordination of the lithium atom to the chloride leaving group, and the most favorable amination pathway occurred by a backside attack of the nitrogen nucleophile on chloromethane.
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