title: Aluminium-mediated aromatic C-F bond activation: regioswitchable construction of benzene-fused triphenylene frameworks.
abstract: Selective synthesis of benzo[f]tetraphenes or benzo[g]chrysenes was achieved via aromatic C-F bond cleavage and unprecedented regioselective C-C bond formation depending upon the choice of aluminium reagents. On treatment with AlCl3, 2-(biphenyl-2-yl)-1-fluoronaphthalenes afforded exclusively benzo[f]tetraphenes via C-C bond formation on the carbon atom γ to the original position of the fluorine substituent. In contrast, α-selective C-C bond formation was promoted by treatment with γ-Al2O3to give benzo[g]chrysenes.
authors.affiliation: Division of Chemistry, Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan. junji@chem.tsukuba.ac.jp.
authors.forename: Naoto
authors.initials: N
authors.lastname: Suzuki
authors.affiliation: Division of Chemistry, Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan. junji@chem.tsukuba.ac.jp.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Fujita
authors.affiliation: Institute of Organic Chemistry II, University of Erlangen-Nürnberg, Henkestr. 42, 91054 Erlangen, Germany.
authors.forename: Konstantin Yu
authors.initials: KY
authors.lastname: Amsharov
authors.affiliation: Division of Chemistry, Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan. junji@chem.tsukuba.ac.jp.
authors.forename: Junji
authors.identifier: http://orcid.org/0000-0001-6498-326X
authors.initials: J
authors.lastname: Ichikawa