NIS/TEMPO‐Promoted Oxidative Cyanation and Nitro‐Mannich Reaction of Tertiary Amines

Abstract A metal‐free N‐iodosuccinimde (NIS)/2,2,6,6‐tetramethylpiperidinyloxy (TEMPO)‐promoted protocol was developed for the oxidative cyanation and nitro‐Mannich reaction of tertiary amines via a cross‐dehydrogenative coupling reaction under mild conditions. Several control experiments were performed; the coupling reaction outcomes indicated that the C−N coupled intermediate ( N ‐Mannich base) formed from the tertiary amine and NIS had a stabilizing effect on the iminium cation.