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Palladium‐Catalyzed Amination of Aryl Sulfides with Anilines
Author(s) -
Sugahara Tomohiro,
Murakami Kei,
Yorimitsu Hideki,
Osuka Atsuhiro
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201404355
Subject(s) - amination , aryl , chemistry , palladium , organic chemistry , catalysis , sulfoxide , combinatorial chemistry , pummerer rearrangement , acetic anhydride , alkyl
A combination of a palladium–NHC catalyst and potassium hexamethyldisilazide enables the amination of aryl sulfides with anilines to afford a wide variety of diarylamines. The reaction conditions are versatile enough for the reaction of even bulky ortho ‐substituted aryl sulfides. This amination can be applied to the modular synthesis of N‐aryl carbazoles from the corresponding ortho ‐bromothioanisoles. As aryl sulfoxides undergo extended Pummerer reactions to afford ortho ‐substituted aryl sulfides, the Pummerer products are thus useful substrates for the amination to culminate in efficient syntheses of a 2‐anilinobenzothiophene and an indole as proof‐of‐principle of the utility of the extended Pummerer reaction/amination cascade.