The N-heterocyclic imine (NHI) is a strong donor ligand. We show its ability to tame and permit structural authentication of hitherto unknown organic electrophiles, including the first example of a doubly protonated superelectrophile. Next, we introduce a new class of strongly donating N-heterocyclic boryloxy (NHBO) ligand based on the isoelectronic analogy with the NHI, which allows access to the first dioxysilylene and its heavier congeners. Lastly, we show the first acid-free anionic oxoborane with a terminal B=O double bond derived from the NHBO framework, and its reactivity as an oxide ion transfer agent.

From N-heterocyclic imine to N-heterocyclic boryloxy derived main group species

ACS Spring 2022

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