title: Biaryl synthesis by ring-opening Friedel-Crafts arylation of 1,4-epoxy-1,4-dihydronaphthalenes catalyzed by iron trichloride.
abstract: Biaryl and heterobiaryl compounds are important frameworks across a range of fields including pharmaceutical and functional material chemistries. We have accomplished the efficient synthesis of various naphthalene-linked arenes and heteroarenes as biaryls and heterobiaryls by the FeCl3 -catalyzed Friedel-Crafts reactions accompanied by the ring-opening of the 1,4-epoxy moiety of 1,4-epoxy-1,4-dihydronaphthalenes. Especially, it is noteworthy that 1-silylated substrates were regioselectively transformed to the 3-aryl-1-silylnaphthalenes and the double Friedel-Crafts reactions using thiophene derivatives could directly produce the corresponding bis-naphthlated thiophene derivatives.
authors.affiliation: Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigakunishi, Gifu 501-1196 (Japan). sawama@gifu-pu.ac.jp.
authors.forename: Yoshinari
authors.initials: Y
authors.lastname: Sawama
authors.forename: Shota
authors.initials: S
authors.lastname: Asai
authors.forename: Takahiro
authors.initials: T
authors.lastname: Kawajiri
authors.forename: Yasunari
authors.initials: Y
authors.lastname: Monguchi
authors.forename: Hironao
authors.initials: H
authors.lastname: Sajiki
mesh_terms: D002384:Catalysis; D007501:Iron / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009281:Naphthalenes; D007501:Iron
keywords: Friedel-Crafts reaction; arenes; biaryls; iron catalyst; ring-opening reaction