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Updated: Mar 13, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Aluminium-mediated aromatic C-F bond activation: regioswitchable construction of benzene-fused triphenylene
Naoto Suzuki1, Takeshi Fujita1, Konstantin Yu Amsharov2
1Division of Chemistry, Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan. junji@chem.tsukuba.ac.jp.
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-Al2O3 to give benzo[g]chrysenes.
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