Table 1 The Friedel–Crafts benzylation reactions of toluene with
various reactant substrates catalyzed by 1a
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2
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2
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a
b
Conversion (%)
Entry
Substrates
Time/h
12
1
499
3
4
2
89.8
12
12
(a) R. Robson, J. Chem. Soc., Dalton Trans., 2000, 3735–3744;
(
M. Schroder, Acc. Chem. Res., 2005, 38, 335–350.
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¨
5
(a) O. D. Friedrichs, M. O’Keeffe and O. M. Yaghi, Acta
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3
0
(
b) I. A. Baburin, V. A. Blatov, L. Carlucci, G. Ciani and
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a
All reactions were performed under the same reaction conditions
b
(
(ESIw). Determined by GC-MS, based on starting materials.
In conclusion, through layered-solvothermal reaction, a 3-D
6
Frontiers in Crystal Engineering, ed. E. R. T. Tiekink and
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porous rutile-type zinc(II)-phosphonocarboxylate framework
1
a
was successfully isolated based on the preselected
3
-connected ligand. 1a shows excellent size-selective properties
7
8
9
for Friedel–Crafts benzylation reaction due to the regular
porosities. The catalysis activity should be ascribed to the
unique structural property of 1a.
This research work was supported financially by Shanghai
Leading Academic Discipline Project (Project No. B108).
2
005, 2402–2404; (c) R. Natarajan, G. Savitha, P. Dominiak,
K. Wozniak and J. N. Moorthy, Angew. Chem., Int. Ed., 2005,
4, 2115–2119.
Notes and references
4
y Synthesis of {[Zn
3
(pbdc)
0.025 g, 0.1 mmol) and triethylamine (0.04 g, 0.4 mmol) in i-PrOH
5 ml) was carefully layered onto a solution of Zn(CH COO)
ꢀ2H
0.32 g, 0.15 mmol) in deionized water (5 mL) in a Teflon-lined
2
]ꢀ2H
3
O}
n
(1a). A solution of H
4
pbdc
10 (a) N. W. Ockwig, O. Delgado-Friedrichs, M. O’Keeffe and
O. M. Yaghi, Acc. Chem. Res., 2005, 38, 176–182;
(
(
(
3
2
2
O
(b) V. A. Blatov, L. Carlucci, G. Ciani and D. M. Proserpio,
CrystEngComm, 2004, 6, 378–395.
stainless steel autoclave (15 mL). The mixture was heated at 140 1C
for 3 days, followed by cooling to room temperature. Colorless rod-
shaped crystals of 1a were collected by filtration (yield: 17% based on
1
1
1 (a) S. R. Batten, CrystEngComm, 2001, 3, 67–73; (b) http://www.
chem.monash.edu.au/staff/sbatten/interpen/index.html.
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D. B. Moler, M. O’Keeffe and O. M. Yaghi, J. Am. Chem. Soc.,
H
4
pbdc). Elemental analysis calcd for 1a C16
H
12
P
2
O
16Zn
3
(718.3): C,
ꢂ1
26.75; H, 1.68%. Found: C, 26.71; H, 1.73%. IR (cm ): 3436 m,
3068 w, 2984 w, 1614 s, 1567 m, 1436 m, 1368 m, 1310 w, 1211 m,
1110 m, 1012 m, 990 m, 777 m, 729 m, 574 m, 457 m.
1
6 14 2 3 3
z Crystal data for 1a. C16H O P Zn , 2(H O), M = 718.31,
2
001, 123, 8239–8247; (b) J. H. He, Y. T. Zhang, Q. H. Pan,
J. H. Yu, H. Ding and R. R. Xu, Microporous Mesoporous Mater.,
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4 (a) L. Alaerts, E. Se
P. A. Jacobs and D. E. De Vos, Chem.–Eur. J., 2006, 12,
353–7363; (b) C.-L. Chen, A. M. Goforth, M. D. Smith,
T = 293(2) K, tetragonal, I-42d, a = 18.310(6), b = 18.310(6),
= 1.226 g cm
3
c = 23.222(11) A, V = 7785(5) A , Z = 8, D
m = 1.964 mm , F(000) = 2848, GOF = 1.18, Flack = 0.28(3), R
ꢂ3
˚
˚
c
,
2
ꢂ1
1
1
´
guin, H. Poelman, F. Thibault-Starzyk,
and wR
2
are 0.0402 and 0.1471, respectively, for 18 703 total data and
079 observed data [I 4 2s(I)], Rint = 0.0527. CCDC 746203.
Crystal data for 1b. C16 Zn , 2(H O), M = 718.31, T =
93(2) K, tetragonal, I-42d, a = 18.218(4), b = 18.218(4), c =
3
7
H
6
O
14
P
2
3
3
C.-Y. Su and H.-C. z. Loye, Angew. Chem., Int. Ed., 2005, 44,
6673–6677; (c) R. D. Adams, B. Captain, C. Beddie and
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5 M. Sadakiyo, T. Yamada and H. Kitagawa, J. Am. Chem. Soc.,
2
2
3
ꢂ3
˚
˚
3.552(7) A, V = 7817(3) A , Z = 8, D
c
= 1.221 g cm
,
ꢂ1
m = 1.956 mm , F(000) = 2848, GOF = 1.08, Flack = 0.50(5),
R
1
2
and wR are 0.0649 and 0.1935, respectively, for 15733 total data
1
and 2140 observed data [I 4 2s(I)], Rint = 0.1222. CCDC 746472.
2
009, 131, 9906–9907.
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J.-S. Chang, J.-M. Greneche, I. Margiolakid and G. Fe
Commun., 2007, 2820–2822.
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1
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102 | Chem. Commun., 2010, 46, 1100–1102
This journal is ꢁc The Royal Society of Chemistry 2010