A convenient one-pot synthesis of amines from aldoximes mediated by Koser’s reagent

Abstract

A simple and convenient procedure has been developed for the synthesis of aromatic amine by a one-pot reaction of aromatic aldoxime with hypervalent iodine(III) reagent [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser's reagent), in an alkaline medium. The aldoxime reacts with Koser's reagent to form an intermediate hydroxamic acid, which then undergoes Lossen type rearrangement to produce the desired amine. Several amines have been prepared which otherwise are difficult to prepare, by the reduction of corresponding nitro compounds. The scopes and limitations of this transformation have been discussed.