Iodination of both deactivated and activated arenes with sodium periodate or sodium iodate as the oxidants

Five easy, relatively inexpensive, and environmentally-safe aromatic oxidative iodination procedures are presented; three of them are particularly suitable for deactivated arenes. Nine deactivated arenes, four halobenzenes, benzene, toluene, and N,N-dimethylaniline were reacted upon with the following anhydrous systems: diiodine/NaIO4 or (in four cases) NaIO3/acetic anhydride/glacial acetic acid, acidified with varying amounts of coned (98%) sulfuric acid; the following workups are explained. The aromatic oxidative iodination reactions proceeded mostly at room temperature and within 1-8 h to give fifteen mono- and two diiodinated purified products (sometimes obtained in 2-3 different ways) in 51-95% yields.