Nucleophilic Acylation-Annulation Cascade of 2-Chlorobenzonitriles Using Aldehydes Triggered by N-Heterocyclic Carbenes.

A general and practical route to the synthesis of functionalized isoindolin-2-ones from commercially available aldehydes and 2-chlorobenzonitriles under mild conditions initiated by N-heterocyclic carbenes is presented. The catalytically generated Breslow intermediates from aldehydes and carbenes underwent smooth S N Ar with 2-chlorobenzonitriles followed by annulation triggered by adventitious water present in DMF to furnish the functionalized isoindolin-2-ones in good to excellent yields.