Study on Radical Amidation onto Aromatic Rings with (Diacyloxyiodo)arenes

Abstract

Sulfonamides of primary amines bearing an aromatic ring at the γ-position were treated with (diacyloxyiodo)arenes and iodine under irradiation conditions with a tungsten lamp to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in moderate to good yields. Here, the reactivity depends on the Z-group (protecting group) of the starting amides. Under the same reaction conditions, some sulfonamides were treated with (diacetoxyiodo)benzene and iodine in the presence of aromatics to give the corresponding N-arylated amides. These reactions proceed through the intramolecular and intermolecular amidations onto aromatic rings via the sulfonamidyl radicals formed.