JOURNAL OF
POLYMER SCIENCE
ORIGINAL ARTICLE
TABLE 4 Sonogashira–Hagihara Coupling Reaction Catalyzed by
TbPo-Pd(II)
oxygen, total separation from the reaction products, and reus-
ability may be helpful to use TbPo-Pd(II) on an industrial
scale. This work also highlights that the TbPo can not only dis-
play strong metal binding capacity as support materials but
also positively affect the catalytic activity. Finally, we expect
a
Base Cat. Temp.
I
+
R
MeOH:H
2
O(3:2) 5mL
R
2 2
that the N O type polymers will find extensive application,
via the advantage of coordinating various transition metals, in
other fields of research and in catalytic applications.
b
Entry
Substrate
Time (h)
12
Conversion (%)
93.9
c
1
ACKNOWLEDGMENTS
I
The authors acknowledge financial support from the National Nat-
ural Science Foundation of China (21473064), Shenzhen Science
and Technology Innovation Program (JCYJ20150630155150201),
Innovation Foundation of Huazhong University of Science and
Technology (2015TS151). The authors thank for the analysis sup-
plied by the Analytical and Testing Center, Huazhong University of
Science and Technology, Wuhan, China.
2
3
14
14
95.2
99.9
I
I
F3CO
a
Reaction conditions: aryl halide (1.0 mmol), phenylacetylene (1.5 mmol),
ꢀ
5
mL of MeOH/H
2
O (3:2 vol/vol), 0.35 mmol % Pd(II), 80 C, in air.
REFERENCES AND NOTES
b
c
Determined by GC.
ꢀ
ꢀ
1
00 C.
1 A. Molnár, Chem. Rev. 2011, 111, 2251.
2
1
N. Miyaura, A. Suzuki, J. Chem. Soc. Chem. Commun.
979, 866.
(
(
92%), and the time was shorter than the case of Fe O /P
3 4
GMA-AA-MMA)-Schiff base-Pd. The TbPo-Pd(II) is a promis-
5
3
3
M. Lamblin, L. Nassar-Hardy, J. C. Hierso, E. Fouquet,
F. X. Felpin, Adv. Synth. Catal. 2010, 352, 33.
ing candidate showing excellent catalytic activity in short time
and low temperature.
4
M. Gholinejad, F. Hameda, P. Biji, Dalton Trans. 2015, 44,
1
4293.
5
R. Kore, M. Tumma, R. Srivastava, Catal. Today 2012,
Application of TbPo-Pd(II) in Sonogashira–Hagihara
Reaction
198, 189.
6 Z. Feng, Q. Min, H. Zhao, J. Gu, X. Zhang, Angew. Chem. Int.
Ed. 2014, 53, 1.
Here we report a short study of the Sonogashira–Hagihara
reaction with TbPo-Pd(II) catalyst. The Sonogashira–Hagihara
coupling reaction was conducted following the optimal condi-
tion of the Suzuki–Miyaura coupling reaction. The results of
these reactions are shown in Table 4. In all cases, the yields of
coupling products were higher than 90%. As can be deduced
from Table 4, the presence of electron-donors or electron-
withdrawing groups in the aryl bromide does not affect yields
7 M. A. Zolfigol, V. Khakyzadeh, A. R. Moosavi-Zare, A. Rostami,
A. Zare, N. Iranpoor, M. H. Beyzavie, R. Luque, Green Chem.
2
8
9
013, 15, 2132.
A. J. Amali, R. K. Rana, Green Chem. 2009, 11, 1781.
N. T. S. Phan, P. Styring, Green Chem. 2008, 10, 1055.
10 P. Da, W. Linert, Coord. Chem. Rev. 2016, 311, 1.
11 N. T. S. Phan, M. V. D. Sluys, C. W. Jones, Adv. Synth. Catal.
2
006, 348, 609.
(
entries 1–3). The data in Tables 2 and 4 indicated that TbPo-
1
2 S. Sabaqian, F. Nemati, H. T. Nahzomi, M. M. Heravi, Carbo-
Pd(II) showed excellent performance for the Suzuki–Miyaura
and Sonogashira–Hagihara coupling reactions. It is certain that
the TbPo-Pd(II) has great potential application for the C–C
coupling reactions.
hydr. Polym. 2017, 177, 165.
1
1
1
1
3 A. Suzuki, Angew. Chem. Int. Ed. 2011, 50, 6723.
4 G. C. Fortman, S. P. Nolan, Chem. Soc. Rev. 2011, 40, 5151.
5 Y. Tsuji, T. Fujihara, Inorg. Chem. 2007, 46, 1895.
6
A. W. Augustyniak, W. Zawartka, J. A. R. Navarro,
CONCLUSIONS
A. M. Trzeciak, Dalton Trans. 2016, 45, 13525.
1
1
7 L. Chen, S. Rangan, J. Li, H. Jiang, Y. Li, Green Chem. 2014,
6, 3978.
In this study, we reported a novel strategy that polymer-
supported palladium (II) containing N O active center was an
2 2
1
8 E. Guillén, R. Rico, J. M. López-Romero, J. Bedia,
efficient and robust heterogeneous catalyst for C–C coupling
reactions, and the polymer could be synthesized via Schiff
base condensation reaction with facile and cost-effective syn-
thesis approach. The Suzuki–Miyaura and Sonogashira–
Hagihara coupling reactions catalyzed by TbPo-Pd(II) could be
proceeded smoothly in the aqueous solution with excellent
activity and selectivity. Meanwhile, the structure and composi-
tion of TbPo-Pd(II) and Tbpo were fully characterized by
FTIR, TGA, XPS, AAS, SEM, and TEM analyses. Furthermore,
the stability at relatively high temperatures, insensitivity to
J. M. Rosas, J. Rodríguez-Mirasol, T. Cordero, Appl. Catal. A
Gen. 2009, 368, 113.
1
9 A. A. Kurokhtina, E. V. Larina, A. F. Schmidt, A. Malaika,
B. Krzy z_ y nꢀ ska, P. Rechnia, M. Kozłowski, J. Mol. Catal. A Chem.
2
2
013, 379, 327.
0 S. Lu, Y. Hu, S. Wan, R. McCaffrey, Y. Jin, H. Gu, W. Zhang,
J. Am. Chem. Soc. 2017, 139, 17082.
2
1 R. S. B. Gonçalves, A. B. V. d. Oliveira, H. C. Sindra,
B. S. Archanjo, M. E. Mendoza, L. S. A. Carneiro, C. D. Buarque,
P. M. Esteves, ChemCatChem 2016, 8, 743.
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