We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Palladium-Catalyzed Amination of Aryl Sulfides with Anilines.
- Authors
Sugahara, Tomohiro; Murakami, Kei; Yorimitsu, Hideki; Osuka, Atsuhiro
- Abstract
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.
- Subjects
PALLADIUM metallurgy; AMINATION kinetics; CARBAZOLE; ANILINE; PUMMERER rearrangement
- Publication
Angewandte Chemie International Edition, 2014, Vol 53, Issue 35, p9329
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201404355