Synthesis of Cyclohexenone(aryl)iodonium Salts and Their Application in Construction of Fused aza‐Heterocyclic Skeletons

Abstract

AbstractA class of cyclohexenone(aryl)iodonium salts was readily prepared from 2‐iodocyclohexenones and arenes under mild conditions. This novel series of hypervalent iodonium building blocks exhibits dual characteristics of hyperiodonium salts and α,β‐unsaturated cyclic ketones, enabling access to intricate aza‐heterocycles. The reaction of these cyclohexenone(aryl)iodonium salts with arylamines or aryl sulfonamides affords 2‐acylaziridines, while with 2‐aminobenzimidazoles or 2‐aminoimidazoles leads to the formation of the 1H‐imidazo[1,2‐a]imidazole‐fused compounds. The transformation is postulated to proceed through an exclusive hyperiodonium‐mediated N‐Michael addition followed by N‐annulation cascade.