Rhodium(II)-Catalyzed Synthesis of N-Aryl-N′-tosyldiazenes from Primary Aromatic Amines Using (Tosylimino)aryliodinane: A Potent Stable Surrogate for Diazonium Salts
A single-step synthesis of N-aryl-N′-tosyldiazenes from primary aromatic amines was developed. A wide range of aromatic amines provided the corresponding products in high yields by N–N bond formation with RhII–nitrene intermediates, which were generated in situ from dirhodium(II) complex catalysts and (tosylimino)-2,4,6-trimethylphenyliodinane, followed by oxidation. The synthesized N-aryl-N′-tosyldiazenes were successfully demonstrated to serve as potent and stable surrogates for diazonium salts in the two-step deaminative transformation of primary aromatic amines.