J. Y. Kim, J. C. Park, A. Kim, A. Y. Kim, H. J. Lee, H. Song, K. H. Park
SHORT COMMUNICATION
Experimental Section
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Preparation of Cu
dissolved in PD (Aldrich, 96%; 45 mL) was heated to 240 °C under
an inert atmosphere. Then, Cu(acac) (STREM, 98%; 4.0 mmol)
dissolved in PD (15 mL) was injected into the hot PVP solution at
40 °C, and the mixture was stirred for 15 min at the same tempera-
2
O Nanocubes: PVP (Aldrich, Mw 55,000; 5.3 g)
2
2
ture. The colloidal dispersion was cooled to room temperature, and
the product was separated by adding acetone (150 mL) and centri-
fuging at 8000 rpm for 20 min. The precipitates were washed with
ethanol several times and re-dispersed in ethanol (50 mL).
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2
002, 67, 5553–5566; i) A. V. Vorogushin, X. Huang, S. L.
Cu
2
O
nanocubes (2 mg, 0.1 mol-%), iodobenzene (1.6 mL,
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0.014 mol), phenol (1.3 g, 0.014 mol), Cs
2
3
and THF (10 mL). The reaction mixture was stirred at 150 °C in
air. After three hours, the reaction mixture was poured into satu-
1
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rated aqueous NaHCO
tracted with dichloromethane (3ϫ20 mL) and dried with MgSO
The Cu O nanocubes were recovered by centrifugation, and the
3
solution (20 mL). The product was ex-
4
.
2
clean solution was analyzed by 300 MHz NMR spectroscopy.
1H NMR Spectroscopic Data
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[
10a]
2A,[10a] 3A,[10b] 4A,[10c] 5A,[10d] 6A,[10e] and
Compounds 1A,
[
10a]
7A
are known compounds.
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1
Diphenyl ether (1A): H NMR (CDCl
(
3
, 300 MHz): δ = 7.10–7.17
m, 4 H), 7.19–7.22 (m, 2 H); 7.36–7.44 (m, 4 H) ppm.
1
1
-Methyl-4-phenoxybenzene (2A): H NMR (CDCl
2.43 (s, 3 H), 7.09 (d, J = 8.4 Hz, 2 H), 7.14–7.19 (m, 3 H), 7.22
d, J = 8.1 Hz, 2 H), 7.40 (t, J = 7.8 Hz, 2 H) ppm.
3
, 300 MHz): δ
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=
(
1
1
-Methoxy-4-phenoxybenzene (3A): H NMR (CDCl
δ = 3.78 (s, 3 H), 6.85–6.91 (m, 2 H), 6.94–6.99 (m, 4 H), 7.01–7.06
m, 1 H), 7.26–7.32 (m, 2 H) ppm.
3
, 300 MHz):
(
1
1
6
7
-Nitro-4-phenoxybenzene (4A): H NMR (CDCl
.81–6.83 (m, 2 H), 7.00–7.06 (m, 2 H), 7.22–7.25 (m, 1 H), 7.61–
.65 (m, 2 H), 8.06–8.09 (m, 2 H) ppm.
3
, 300 MHz): δ =
1
1
-Methyl-3-phenoxybenzene (5A): H NMR (CDCl
2.20 (s, 3 H), 6.70–6.73 (m, 2 H), 6.79 (d, J = 9.6 Hz, 1 H), 6.90
d, J = 7.8 Hz, 2 H), 6.94–6.99 (m, 1 H), 7.03–7.11 (m, 1 H), 7.17–
3
, 300 MHz): δ
=
(
5
84; f) C. Wolf, S. Liu, X. Mei, A. T. August, M. D. Casimir,
7.20 (m, 2 H) ppm.
J. Org. Chem. 2006, 71, 3270–3273; g) Y. Pan, H. Lu, Y. Fang,
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8092–8093.
2
7
(
-Naphthyl phenyl ether (6A): 1H NMR (CDCl
.01–7.16 (m, 3 H), 7.25–7.27 (m, 1 H), 7.25–7.47 (m, 5 H), 7.69
d, J = 7.5 Hz, 1 H), 7.80–7.83 (m, 2 H) ppm.
3
, 300 MHz): δ =
[
[
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1
1
-Methyl-2-phenoxybenzene (7A): H NMR (CDCl
7.22–7.30 (m, 3 H), 7.08–7.16 (m, 1 H), 6.92–6.99 (m, 2 H), 6.85–
.90 (m, 3 H), 2.29 (s. 3 H) ppm.
3
, 300 MHz): δ
=
6
Supporting Information (see footnote on the first page of this arti-
cle): Magnified TEM images of Cu
photo of the reaction vessel.
2
480; d) C. N. R. Rao, A. K. Cheetham, J. Mater. Chem. 2001,
2 2
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Acknowledgments
4
This research was supported by the Basic Science Research Pro-
gram through the National Research Foundation of Korea (NRF)
funded by the Ministry of Education, Science and Technology
Weinheim, Germany, 2008.
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(
(
2009-0070926) and by the Korean Research Foundation Grant
KRF-2006-312-C00565).
4222
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Eur. J. Inorg. Chem. 2009, 4219–4223