title: NH-Heterocyclic Aryliodonium Salts and their Selective Conversion into N1-Aryl-5-iodoimidazoles.
abstract: The synthesis of N-arylimidazoles substituted at the sterically encumbered 5-position is a challenge for modern synthetic approaches. A new family of imidazolyl aryliodonium salts is reported, which serve as a stepping stone on the way to selective formation of N1-aryl-5-iodoimidazoles. Iodine acts as a "universal" placeholder poised for replacement by aryl substituents. These new λ(3) -iodanes are produced by treating the NH-imidazole with ArI(OAc)2 , and are converted to N1-aryl-5-iodoimidazoles by a selective copper-catalyzed aryl migration. The method tolerates a variety of aryl fragments and is also applicable to substituted imidazoles.
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
authors.forename: Yichen
authors.initials: Y
authors.lastname: Wu
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.
authors.forename: Susana
authors.initials: S
authors.lastname: Izquierdo
authors.affiliation: Departament de Química, Universitat Autònoma de Barcelona, 08193, Cerdanyola del Vallès, Spain.
authors.forename: Pietro
authors.initials: P
authors.lastname: Vidossich
authors.affiliation: Departament de Química, Universitat Autònoma de Barcelona, 08193, Cerdanyola del Vallès, Spain. agusti@klingon.uab.es.
authors.forename: Agustí
authors.initials: A
authors.lastname: Lledós
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain. ashafir@iciq.es.
authors.forename: Alexandr
authors.identifier: 0000-0002-8127-2299
authors.initials: A
authors.lastname: Shafir
keywords: C−H functionalization; C−N coupling; copper catalysis; hypervalent iodine; imidazoles