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ChemComm
Table 2. Oxidation/[3+2] cycloaddition/aromatization tandem reaction
catalyzed by photosensitizers KIT-1-B a
25 a]isoquinoline. To the best of our knowledge, this is the first
COOEt
O
DOI: 10.1039/C3CC44486D
O
O
O
functionalized organic compounds. Our results are useful for
the development of recyclable organic photocatalysts for
30 photoredox catalytic organic reactions.
KIT-1-B
Visible Light
N
N
N
O
5
N
O
NBS, Air
R
3x
R
1
We thank NSFC (21073028, 21273028 and 20773019) the
Royal Society (UK) and NSFC (China-UK Cost-Share
Science Networks, 21011130154), Ministry of Education
(SRFDP-20120041130005) for financial support.
2x
COOEt
O
KIT-1-B
Visible Light
N
O
O
O
10
N
N
N
O
O
NBS, Air
R
35 Notes and references
1
R
2x
3x
State Key Laboratory of Fine Chemicals, School of Chemical Engineering,
E-208 West Campus, Dalian University of Technology, Dalian 116024, P.
R. China. E-mail: zhaojzh@dlut.edu.cn and gxiong@dlut.edu.cn
Entry
1
Substrates
O
Product
COOEt
t / [h] b Yield c
1
1
80
N
O
40 † Electronic Supplementary Information (ESI) available: molecular
N
N
structural
characterization
and
mechanism
studies.
See
2a
O
O
3a
DOI: 10.1039/b000000x/
2
3
COOEt
O
O
1 (a) D.-P. Hari and B. König, Angew. Chem. Int. Ed., 2013, 52, 4734; (b)
J. Narayanam and C. Stephenson, Chem. Soc. Rev., 2011, 40, 102; (c) D.
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T.-E. Weirich and J. Mayer, Chem. Eur. J., 2012, 18, 3478; (b) W. Li,
60 W. Zhang, X. Dong, L. Yan, R. Qi, W. Wang, Z. Xie, X. Jing. J. Mater.
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65 7 (a) Y.-Q. Zou, L. –Q. Lu, L. Fu, N.-J. Chang, J. Rong, J.-R. Chen and
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Zhao, Chem. Commun., 2013, 49, 3751.
75
N
N
Br
N
O
O
2b
3b
Br
O
COOEt
O
1
1
77
72
N
N
OCH3
O
2c
N
O
3c
OCH3
4
O
COOEt
O
N
N
NO2
N
O
O
2d
3d
NO2
5
6
7
COOEt
O
2
2
2
68
60
51
N
O
N
N
2e
O
O
3e
F
COOEt
N
O
N
O
F
8
(a) A. Kamkaew, S.-H. Lim, H.-B. Lee, L.-V. Kiew, L.-Y
Chung and K. Burgess, Chem. Soc. Rev, 2013, 42, 77; (b) S. -G.
N
O
2f
70 Awuah and Y. You, RSC Adv., 2012, 2, 11169; (c) J. Zhao, W. Wu, J.
Sun and S. Guo, Chem. Soc. Rev., 2013, 42, 5323.
9 L. Huang, J. Zhao, S. Guo, C. Zhang, and J. Ma, J. Org. Chem., 2013,
3f
O
OCH3
COOEt
N
O
O
OCH3
78, 5627.
N
10 (a) X. Hong, Z. Wang, J. Yang, Q. Zheng, S. Zong, Y. Sheng, D. Zhu,
N
75 C. Tang and Y. Cui, Analyst, 2012, 137, 4140; (b) N. -E. -A. El-Gamel,
O
2g
3g
O
L. Wortmann, K. Arroubb, S. Mathur, Chem. Commun., 2011, 47,
15 a Reaction conditions: 1a or 1b (0.15 mmol), 2 (0.10 mmol), KIT-1-B (10
mg) and N-bromosuccinimide (NBS, 1.2 equiv) were mixed in CH3CN
(3.0 mL), the mixture was photoirradiated with 35 W Xenon lamp (λ >
385 nm), 20 °C. b Reaction time with photosensitizers. c Yield of isolated
products catalyzed with KIT-1-B.
10076.
11 X. Gu, X. Li, Y. Chai, Q. Yang, P. Li and Y. Yao, Green Chem., 2013,
15, 357.
80
20
In summary, organic photocatalyst showing strong
absorption of visible light was immobilized to mesoporous
material
KIT-1.
The
solid-supported
photocatalyst
demonstrated high photocatalytic activity toward the tandem
oxidation/[3+2] cycloaddition to prepare pyrrolo[2,1-
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