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

Naoto Suzuki | Zendy; Takeshi Fujita | Zendy; Konstantin Amsharov | Zendy; Junji Ichikawa | Zendy

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

Author(s) -

Naoto Suzuki,

Takeshi Fujita,

Konstantin Amsharov,

Junji Ichikawa

Publication year - 2016

Publication title -

chemical communications

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.837

H-Index - 333

eISSN - 1364-548X

pISSN - 1359-7345

DOI - 10.1039/c6cc07199f

Subject(s) - triphenylene , chemistry , biphenyl , regioselectivity , substituent , bond cleavage , benzene , reagent , fluorine , aluminium , stereochemistry , electrophilic aromatic substitution , medicinal chemistry , organic chemistry , catalysis , molecule

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 AlCl 3 , 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-Al 2 O 3 o give benzo[g]chrysenes.

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