title: Direct arylation of oligonaphthalenes using PIFA/BF3·Et2O: from double arylation to larger oligoarene products.
abstract: Direct dehydrogenative coupling between the linear ter- and quaternaphthalenes and substituted benzenes was achieved under the Kita conditions using the hypervalent PIFA/BF3 reagent. Products resulting from either the double arylation of the naphthalenic substrate or the formal dimerizative arylation have been prepared. For example, in the latter mode, ternaphthalene was converted into a series of linear octiarenes (counting the capping Ar). The process represents an alternative to the cross-coupling methodologies employed in related syntheses and proceeds via a selective functionalization of six relatively inert aromatic CH bonds.
authors.affiliation: Department of Chemistry, Universitat Autònoma de Barcelona, 08193-Cerdanyola del Vallès, Barcelona, Spain.
authors.forename: Wusheng
authors.initials: W
authors.lastname: Guo
authors.forename: Enrico
authors.initials: E
authors.lastname: Faggi
authors.forename: Rosa M
authors.initials: RM
authors.lastname: Sebastián
authors.forename: Adelina
authors.initials: A
authors.lastname: Vallribera
authors.forename: Roser
authors.initials: R
authors.lastname: Pleixats
authors.forename: Alexandr
authors.initials: A
authors.lastname: Shafir
mesh_terms: D001554:Benzene / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D007462:Iodobenzenes / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry*
chemical_list: D001880:Boranes; D007462:Iodobenzenes; D009281:Naphthalenes; C517666:phenyliodine(III) bis(trifluoroacetate); C101707:boron trifluoride etherate; D014269:Trifluoroacetic Acid; D001554:Benzene