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Updated: Oct 23, 2025
A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
Boraiminolithium: An Iminoborane-Transfer Reagent
1School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China.
Abstract:
BN/CC isosterism can give rise to attractive molecules with unique physical or chemical properties. We report here the synthesis, characterization, and reactivities of the boraiminolithium species 2, a room-temperature-stable crystalline solid accessible through a facile dehydrohalogenation/deprotonation reaction. This species, bearing a polarized B≡N triple bond and an anionic N center, is the first example of a BN analogue to the well-known alkynyllithium molecules (lithium acetylides). It has demonstrated a remarkable ability for iminoborane-transfer reactions, which allows for the isolation of a series of unprecedented N-functionalized iminoboranes as well as novel main-group heterocycles. Stable boraiminolithium reagents may become powerful tools in the exploration of new BN-containing building blocks for synthetic chemistry and materials science.
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