title: Aromatic Metamorphosis of Dibenzofurans into Triphenylenes Starting with Nickel-Catalyzed Ring-Opening C-O Arylation.
abstract: A new class of aromatic metamorphosis has been developed in which dibenzofurans were converted into triphenylenes. This transformation is composed of three successive operations: (1) nickel-catalyzed ring-opening C-O bond arylation with arylmagnesium bromides, (2) trifluoromethanesulfonylation (triflation) of the resulting hydroxy moiety with Tf2O, and (3) palladium-catalyzed or photoinduced ring closure. In the last ring-closing step, the photoinduced process has proven to be more productive than the palladium-catalyzed one. By employing π-extended dinaphthofuran as the substrate, dorsally benzo-fused [5]helicene was obtained in a satisfactory yield.
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University , Sakyo-ku, Kyoto 606-8502, Japan.
authors.forename: Yuto
authors.initials: Y
authors.lastname: Kurata
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University , Sakyo-ku, Kyoto 606-8502, Japan.
authors.forename: Shinya
authors.identifier: 0000-0001-5598-9707
authors.initials: S
authors.lastname: Otsuka
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University , Sakyo-ku, Kyoto 606-8502, Japan.
authors.forename: Norihito
authors.initials: N
authors.lastname: Fukui
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University , Sakyo-ku, Kyoto 606-8502, Japan.
authors.forename: Keisuke
authors.identifier: 0000-0001-8478-1227
authors.initials: K
authors.lastname: Nogi
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University , Sakyo-ku, Kyoto 606-8502, Japan.
authors.forename: Hideki
authors.identifier: 0000-0002-0153-1888
authors.initials: H
authors.lastname: Yorimitsu
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University , Sakyo-ku, Kyoto 606-8502, Japan.
authors.forename: Atsuhiro
authors.initials: A
authors.lastname: Osuka