Safer Synthesis of (Diacetoxyiodo)arenes Using Sodium Hypochlorite Pentahydrate

Abstract

A practical method for the preparation of (diacetoxyiodo)arene ArI(OAc)₂ is described. The use of commercially available sodium hypochlorite pentahydrate (NaClO·5H₂O) enabled safe, rapid, and inexpensive oxidation of iodoarenes with electron-withdrawing and -donating substituents. The method allows tandem divergent access to synthetically useful organo-λ³-iodanes such as hydroxyl(tosyloxy)iodobenzene, iodosylbenzene, iodonium ylide, etc.