Reactivity Studies and Electronic Properties of an N‑Arylated Acyclic Amino Carbene

Deprotonation of an N-arylated iminium salt affords a new, but unstable, acyclic amino carbene (AAC), which can be efficiently trapped at low temperatures with selected s-, p-, and d-block elements. Whereas the potassium adduct was found to be sensitive, those of sulfur, selenium, gold, rhodium, and palladium are all air- and moisture-stable. A combined experimental and theoretical study on the electronic properties of this new AAC revealed that it is both a good σ-donor and π-acceptor ligand.