0
1
.92 mmol), NaI (163 mg, 1.1 mmol) and Na CO (117 mg,
.1 mmol) under an argon atmosphere at 50 °C. The mixture
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2
3
was heated to reflux for 72 h, and then cooled to room tempera-
ture; solvent was removed under vacuum and the residue was
purified by silica gel column chromatography using 5% MeOH
in CH Cl to afford 4b as a sticky solid (116 mg, 30%): H
NMR (300 MHz, CDCl ): δ 8.52 (2H, m), 8.27 (1H, s), 7.88
4
(a) M. Doherty, C. Becher, M. Regan, A. Jones and J. Ledingham, Ann.
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2
2
3
(
1H, dd, J = 9.0, J = 3.0 Hz), 7.65 (1H, d, J = 9.0 Hz), 7.57 (1H,
dd, J = 9.0, J = 3.0 Hz), 7.52 (2H, m), 7.43 (2H, d, J = 6.0 Hz),
.11 (2H, m), 6.99 (1H, dd, J = 9.0, J = 3.0 Hz), 6.73 (1H, d,
J = 3.0 Hz), 3.92 (4H, s), 3.58 (2H, t, J = 6.0 Hz), 2.99 (3H, s),
6
7
D. H. Vance and A. W. Czarnik, J. Am. Chem. Soc., 1994, 116, 9397.
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7
1
3
41, 3811; (c) S. Mizukami, T. Nagano, Y. Urano, A. Odani and
2
1
1
5
.80 (3H, t, J = 6.0 Hz). C NMR (75 MHz, CDCl ) δ 197.89,
3
K. Kikuchi, J. Am. Chem. Soc., 2002, 124, 3920; (d) D. H. Lee, J. H. Im,
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26.12, 124.89, 124.65, 123.10, 122.29, 116.01, 104.88, 61.08,
1.06, 50.69, 38.90, 26.52. HRMS-EI (+): m/z calcd for
7752; (e) H. N. Lee, Z. Xu, S. K. Kim, K. M. K. Swamy, Y. Kim,
S.-J. Kim and J. Yoon, J. Am. Chem. Soc., 2007, 129, 3828;
(
(
f) H. K. Cho, D. H. Lee and J.-I. Hong, Chem. Commun., 2005, 1690;
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C H N O: 424.55, found 424.23.
2
7
28
4
Chem., 2011, 76, 417; (h) X. Huang, Z. Guo, W. Zhu, Y. Xie and
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1
5
3–Zn(II)
A mixture of 3 (20 mg, 45.6 mmol) and zinc perchlorate hexa-
hydrate (16.98 mg, 45.6 mmol) in CH CN was stirred at room
temperature for 10 h. The reaction mixture was condensed by
evaporation of the solvent under vacuum below 30 °C, and the
residue, after titration with CH Cl and hexane, was filtered to
3
(m) A. Nonaka, S. Horie, T. D. James and Y. Kubo, Org. Biomol. Chem.,
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8
M. J. Kim, K. M. K. Swamy, K. M. Lee, A. R. Jagdale, Y. Kim,
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2
2
give the zinc complex 3–Zn(II) as an off-white solid (hygro-
9 Y. J. Jang, E. J. Jun, Y. J. Lee, Y. S. Kim, J. S. Kim and J. Yoon, J. Org.
Chem., 2005, 70, 9603.
1
scopic) (27 mg, 98%): H NMR (300 MHz, CDCl ): δ 8.75 (2H,
3
10 H. N. Lee, K. M. K. Swamy, S. K. Kim, J.-Y. Kwon, Y. Kim, S.-J. Kim,
d, J = 6.0 Hz), 8.67 (1H, s), 8.21 (1H, d, J = 9.0 Hz), 8.10 (3H,
m), 7.97 (1H, d, J = 9.0 Hz), 7.86 (1H, d, J = 3.0 Hz), 7.70 (2H,
t, J = 6.0 Hz), 7.52 (2H, d, J = 9.0 Hz), 7.43 (1H, dd, J =
Y. J. Yoon and J. Yoon, Org. Lett., 2007, 9, 243.
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1
2 D. H. Lee, S. Y. Kim and J.-I. Hong, Angew. Chem., Int. Ed., 2004, 43,
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4
9
.0 Hz), 4.09 (4H, m), 3.59 (2H, s), 3.41 (3H, s), 2.72 (3H, s).
1
HRMS FAB-(+): m/z calcd for C H ClN O Zn: 603.37, found
2
7
26
4
6
14 K. M. Kim, D. J. Oh and K. H. Ahn, Chem.–Asian J., 2011, 6, 122.
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Chem. Commun., 2012, 48, 3206.
6
03.08.
1
1
1
1
2
6 H. M. Kim and B. R. Cho, Chem.–Asian J., 2011, 6, 58.
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0 X-ray data for 3–Zn(II), M = 817.96: monoclinic, C2/c (No. 15), a =
Acknowledgements
This work was supported by grants from the EPB Center
R11-2008-052-01001).
(
3
7
ρ
0
0
2.024(3) Å, b = 10.6190(9) Å, c = 21.2363(15) Å, β = 90.467(3)°, V =
3
−1
221.5(10) Å , Z = 8, T = 100(2) K, μ(λ = 0.71073 Å) = 0.895 mm
,
=
=
calc = 1.505 g cm− , 31 978 reflections measured, 7111 unique (Rint
3
1 2 1
.1154), R = 0.0599, wR = 0.1148 for 3760 reflections (I > 2σ(I)), R
Notes and references
.1454, wR
2
= 0.1449 (all data), GOF = 0.997. CCDC 876211 contains
1
2
W. N. Lipscomb and N. Strater, Chem. Rev., 1996, 96, 2375.
the supplementary crystallographic data for this paper.
21 Numbers in parentheses are estimated standard deviations in the last
digit(s).
22 M. P. Clares, C. Lodeiro, D. Fernandez, A. J. Parola, F. Pina, E. Garcia-
Espana, C. Soriano and R. Tejero, Chem. Commun., 2006, 3824.
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Org. Biomol. Chem.
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