Iodine-catalyzed synthesis of N,N′-diaryl-o-phenylenediamines from cyclohexanones and anilines using DMSO and O2 as oxidants

Abstract

A novel I₂-catalyzed cross-dehydrogenative aromatization of cyclohexanones and anilines to synthesize N,N′-diaryl-o-phenylenediamines has been unprecedentedly developed with dimethyl sulfoxide and oxygen employed as mild terminal oxidants. To prove the rationality of the two separate dehydration steps of the proposed mechanism, a resulting I₂-catalyzed cross-dehydrogenative aromatization of cyclohexenones and anilines to synthesize diarylamines has also been reported.