<i>N,N</i>′-Diamidoketenimines via Coupling of Isocyanides to an N-Heterocyclic Carbene

Abstract

Treatment of an N-heterocyclic carbene that features two amide groups N-bound to the carbene nucleus with various organic isocyanides afforded a new class of ketenimines in yields of up to 96% (isolated). DFT analyses revealed that the carbene exhibits a unique, low-lying LUMO, which may explain the atypical reactivity observed.