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Rhodium(II)‐Catalyzed Synthesis of N ‐Aryl‐ N′ ‐tosyldiazenes from Primary Aromatic Amines Using (Tosylimino)aryliodinane: A Potent Stable Surrogate for Diazonium Salts
Author(s) -
Ito Motoki,
Tanaka Arisa,
Higuchi Kazuhiro,
Sugiyama Shigeo
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601627
Subject(s) - chemistry , nitrene , aryl , catalysis , primary (astronomy) , rhodium , combinatorial chemistry , diazonium compounds , medicinal chemistry , organic chemistry , alkyl , physics , astronomy
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 Rh II –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.