Palladium-catalyzed amination of aryl sulfides with anilines.

• 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.

Journal

• Angewandte Chemie - International Edition

  Angewandte Chemie - International Edition 53 (35), 9329-9333, 2014-07-07

  wiley

Keywords

• amination
• aryl sulfides
• N-heterocyclic carbene ligands
• palladium
• Pummerer reaction
• Amination
• Amines/chemical synthesis
• Amines/chemistry
• Aniline Compounds/chemistry
• Catalysis
• Heterocyclic Compounds/chemistry
• Methane/analogs & derivatives
• Methane/chemistry
• Molecular Structure
• Organometallic Compounds/chemistry
• Palladium/chemistry
• Sulfides/chemistry

Details

• CRID: 1050001335813436544
• NII Article ID: 120005615640
• NII Book ID: AA0052535X
• ISSN: 14337851
• HANDLE: 2433/198446
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • CiNii Articles