Boraiminolithium: An Iminoborane-Transfer Reagent

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 BN 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.