title: Double heteroatom functionalization of arenes using benzyne three-component coupling.
abstract: Arynes participate in three-component coupling reactions with N, S, P, and Se functionalities to yield 1,2-heteroatom-difunctionalized arenes. Using 2-iodophenyl arylsulfonates as benzyne precursors, we could effectively add magnesiated S-, Se-, and N-nucleophilic components to the strained triple bond. In the same pot, addition of electrophilic N, S, or P reagents and a copper(I) catalyst trapped the intermediate aryl Grignard to produce a variety of 1,2-difunctionalized arenes.
authors.affiliation: School of Chemistry, University of Manchester, Oxford Rd, Manchester, M13 9PL (UK).
authors.forename: José-Antonio
authors.initials: JA
authors.lastname: García-López
authors.forename: Meliha
authors.initials: M
authors.lastname: Çetin
authors.forename: Michael F
authors.initials: MF
authors.lastname: Greaney
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D008958:Models, Molecular; D009584:Nitrogen / Q000737:chemistry; D012643:Selenium / Q000737:chemistry; D013455:Sulfur / Q000737:chemistry
chemical_list: D001555:Benzene Derivatives; C524146:benzyne; D013455:Sulfur; D003300:Copper; D012643:Selenium; D009584:Nitrogen
keywords: Grignard reaction; arynes; benzyne; heterocycles; multicomponent reactions