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Issue 88, 2016
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Aluminium-mediated aromatic C–F bond activation: regioswitchable construction of benzene-fused triphenylene frameworks

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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.

Graphical abstract: Aluminium-mediated aromatic C–F bond activation: regioswitchable construction of benzene-fused triphenylene frameworks

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Supplementary files

Article information


Submitted
03 Sep 2016
Accepted
27 Sep 2016
First published
28 Sep 2016

Chem. Commun., 2016,52, 12948-12951
Article type
Communication

Aluminium-mediated aromatic C–F bond activation: regioswitchable construction of benzene-fused triphenylene frameworks

N. Suzuki, T. Fujita, K. Yu. Amsharov and J. Ichikawa, Chem. Commun., 2016, 52, 12948
DOI: 10.1039/C6CC07199F

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