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ChemComm
DOI: 10.1039/C6CC07199F
COMMUNICATION
Journal Name
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Scheme 4 Cyclisation of an aryl cation intermediate.
1
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,
In summary, we have achieved highly effective cyclisations
of 1-fluoronaphthalenes bearing biaryl groups via aromatic C–F
bond activation mediated by aluminium reagents. It is
noteworthy that the choice of aluminium reagents altered the
regioselectivities in the cyclisation of common 2-(biaryl-2-yl)-1-
fluoronaphthalene precursors, enabling the selective synthesis
of two different benzotriphenylenes, i.e., benzo[f]tetraphenes
and benzo[g]chrysenes. Since higher order PAHs are
particularly promising constituents in organic electronic
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8
,
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For acid-promoted vinylic C–F bond activation, see: (a) J.
Ichikawa, S. Miyazaki, M. Fujiwara and T. Minami, J. Org.
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devices, the formation of extended π-systems by the current
methodology appears to be a powerful route to functional
,
6048–6051; (f) K. Fuchibe, H. Jyono, M. Fujiwara, T. Kudo, M.
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2185; (g) K. Fuchibe, Y. Mayumi, N. Zhao, S. Watanabe, M.
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This work was financially supported by JSPS KAKENHI Grant
Number JP16H04105, JSPS KAKENHI Grant Number
JP16H01002 (J.I.) and the Shorai Foundation for Science and
Technology (T.F.). K.A. is grateful to the Deutsche
,
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and J. Ichikawa, Org. Lett., 2015, 17, 1126–1129; (i) T. Fujita,
Y. Watabe, S. Yamashita, H. Tanabe, T. Nojima and J.
Ichikawa, Chem. Lett., 2016, 45, 964–966.
Forschungsgemeinschaft
for
financial
support.
We
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1
1
A similar regioselectivity was found in an oxidation reaction:
,
acknowledge the generous gifts of Tf
from Central Glass Co., Ltd.
2
O and (CF )
3 2
CHOH (HFIP)
M. Danz, R. Tonner and G. Hilt, Chem. Commun., 2012, 48
77–379.
3
0 For reviews on triphenylene syntheses, see: (a) D. Pérez and
E. Guitián, Chem. Soc. Rev., 2004, 33, 274–283; (b) D. Pérez,
D. Peña and E. Guitián, Eur. J. Org. Chem., 2013, 5981–6013.
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Sergeyev, W. Pisula and Y. H. Geerts, Chem. Soc. Rev., 2007,
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1
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N
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| J. Name., 2012, 00, 1-3
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