title: Palladium-catalyzed amination of aryl sulfides with anilines.
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.
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa, Sakyo-ku, Kyoto 606-8502 (Japan).
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Sugahara
authors.forename: Kei
authors.initials: K
authors.lastname: Murakami
authors.forename: Hideki
authors.initials: H
authors.lastname: Yorimitsu
authors.forename: Atsuhiro
authors.initials: A
authors.lastname: Osuka
mesh_terms: D000586:Amination; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry*
chemical_list: D000588:Amines; D000814:Aniline Compounds; D006571:Heterocyclic Compounds; D009942:Organometallic Compounds; D013440:Sulfides; C030011:carbene; D010165:Palladium; D008697:Methane; C023650:aniline
keywords: N-heterocyclic carbene ligands; Pummerer reaction; amination; aryl sulfides; palladium