Citation: Chengjuan Wu, Xinyu Li, Mingzhen Shao, Jinglan Kan, Guangbo Wang, Yan Geng, Yu-Bin Dong. Porphyrin covalent organic framework for photocatalytic synthesis of tetrahydroquinolines[J]. Chinese Chemical Letters, ;2022, 33(10): 4559-4562. doi: 10.1016/j.cclet.2022.01.065 shu

Porphyrin covalent organic framework for photocatalytic synthesis of tetrahydroquinolines

College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Normal University, Ji'nan 250014, China

gengyan@sdnu.edu.cn

yubindong@sdnu.edu.cn

Received Date: 29 October 2021
Revised Date: 21 January 2022
Accepted Date: 24 January 2022
Available Online: 31 January 2022

Figures(4)

A metal-free porphyrin covalent organic framework was employed as the heterogeneous photocatalyst for the synthesis of tetrahydroquinolines under aerobic conditions. With visible light irradiation of a catalytic amount of H₂P-Bph-COF at room temperature, various substituted N, N-dimethylanilines and N-aryl maleimides were transformed to tetrahydroquinoline derivatives in moderate to good yields. This was the first example of the synthesis of tetrahydroquinolines via the photocatalytic aerobic annulation reaction employing the metal-free COF as the heterogeneous photocatalyst.
- Tetrahydroquinolines,
- Photocatalytic oxidative annulation,
- Covalent organic framework,
- Heterogeneous photocatalyst,
- Porphyrin
1. [1]
  A. Cappelli, C. Nannicini, S. Valenti, et al., ChemMedChem 5 (2010) 739–748. doi: 10.1002/cmdc.200900523
2. [2]
  K. Grychowska, G. Satała, T. Kos, et al., ACS Chem. Neurosci. 7 (2016) 972–983. doi: 10.1021/acschemneuro.6b00090
3. [3]
  J.P. Michael, Nat. Prod. Rep. 20 (2003) 476–493. doi: 10.1039/b208140g
4. [4]
  D.V. Kravchenko, Y.A. Kuzovkova, V.M. Kysil, et al., J. Med. Chem. 48 (2005) 3680–3683. doi: 10.1021/jm048987t
5. [5]
  B. Nammalwar, R.A. Bunce, Molecules 19 (2014) 204–232. doi: 10.3390/molecules19010204
6. [6]
  I. Muthukrishnan, V. Sridharan, J.C. Menéndez, Chem. Rev. 119 (2019) 5057–5191. doi: 10.1021/acs.chemrev.8b00567
7. [7]
  M. Nishino, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 76 (2011) 6447–6451. doi: 10.1021/jo2011329
8. [8]
  N. Sakai, S. Matsumoto, Y. Ogiwara, Tetrahedron Lett. 57 (2016) 5449–5452. doi: 10.1016/j.tetlet.2016.10.071
9. [9]
  Z. Song, A.P. Antonchick, Tetrahedron 72 (2016) 7715–7721. doi: 10.1016/j.tet.2016.04.052
10. [10]
  A.K. Yadav, L.D.S. Yadav, Tetrahedron Lett. 57 (2016) 1489–1491. doi: 10.1016/j.tetlet.2016.02.078
11. [11]
  K. Sharma, B. Das, P. Gogoi, New J. Chem. 42 (2018) 18894–18905. doi: 10.1039/c8nj04443k
12. [12]
  J.Y. Hwang, A.Y. Ji, S.H. Lee, E.J. Kang, Org. Lett. 22 (2020) 16–21. doi: 10.1021/acs.orglett.9b03542
13. [13]
  Q.W. Gui, F. Teng, Z.C. Li, et al., Chin. Chem. Lett. 32 (2021) 1907–1910. doi: 10.1016/j.cclet.2021.01.021
14. [14]
  W.B. He, L.Q. Gao, X.J. Chen, et al., Chin. Chem. Lett. 31 (2020) 1895–1898. doi: 10.1016/j.cclet.2020.02.011
15. [15]
  K. Sun, F. Xiao, B. Yu, W.M. He, Chin. J. Catal. 42 (2021) 1921–1943. doi: 10.1016/S1872-2067(21)63850-0
16. [16]
  C. Hou, H. Liu, F.B. Mohammad, J. Solid State Chem. 300 (2021) 122288. doi: 10.1016/j.jssc.2021.122288
17. [17]
  C. Hou, H. Liu, Y. Li, RSC Adv. 11 (2021) 14957–14969. doi: 10.1039/d1ra01772a
18. [18]
  C.K. Prier, D.A. Rankic, D.W. Macmillan, Chem. Rev. 113 (2013) 5322–5363. doi: 10.1021/cr300503r
19. [19]
  Y. Li, B. Yuan, Z. Sun, W. Zhang, Green Synth. Catal. 2 (2021) 267–274. doi: 10.1016/j.gresc.2021.06.001
20. [20]
  G. Sun, M. Zuo, W. Qian, et al., Green Synth. Catal. 2 (2021) 32–37. doi: 10.1016/j.gresc.2021.01.003
21. [21]
  Y. Ning, T. Ohwada, F.E. Chen, Green Synth. Catal. 2 (2021) 247–266. doi: 10.1016/j.gresc.2021.04.008
22. [22]
  X. Ju, D. Li, W. Li, W. Yu, F. Bian, Adv. Synth. Catal. 354 (2012) 3561–3567. doi: 10.1002/adsc.201200608
23. [23]
  Z. Liang, S. Xu, W. Tian, R. Zhang, Beilstein J. Org. Chem. 11 (2015) 425–430. doi: 10.3762/bjoc.11.48
24. [24]
  T.P. Nicholls, G.E. Constable, J.C. Robertson, M.G. Gardiner, A.C. Bissember, ACS Catal. 6 (2016) 451–457. doi: 10.1021/acscatal.5b02014
25. [25]
  J.T. Guo, D.C. Yang, Z. Guan, Y.H. He, J. Org. Chem. 82 (2017) 1888–1894. doi: 10.1021/acs.joc.6b03034
26. [26]
  A.K. Yadav, L.D.S. Yadav, Tetrahedron Lett. 58 (2017) 552–555. doi: 10.1016/j.tetlet.2016.12.077
27. [27]
  X.L. Yang, J.D. Guo, T. Lei, et al., Org. Lett. 20 (2018) 2916–2920. doi: 10.1021/acs.orglett.8b00977
28. [28]
  J. Li, W. Bao, Y. Zhang, Y. Rao, Org. Biomol. Chem. 17 (2019) 8958–8962. doi: 10.1039/c9ob01946d
29. [29]
  T. Mandal, S. Das, S. De Sarkar, Adv. Synth. Catal. 361 (2019) 3200–3209. doi: 10.1002/adsc.201801737
30. [30]
  A.M. Ranieri, L.K. Burt, S. Stagni, et al., Organometallics 38 (2019) 1108–1117. doi: 10.1021/acs.organomet.8b00913
31. [31]
  J. Mateos, F. Rigodanza, A. Vega-Peñaloza, et al., Angew. Chem. Int. Ed. 59 (2020) 1302–1312. doi: 10.1002/anie.201912455
32. [32]
  G. Perumal, M. Kandasamy, B. Ganesan, et al., Tetrahedron 80 (2021) 131891. doi: 10.1016/j.tet.2020.131891
33. [33]
  Z.J. Wang, S. Ghasimi, K. Landfester, K.A.I. Zhang, Adv. Synth. Catal. 358 (2016) 2576–2582. doi: 10.1002/adsc.201600125
34. [34]
  A.P. Côté, A.I. Benin, N.W. Ockwig, et al., Science 310 (2005) 1166–1170. doi: 10.1126/science.1120411
35. [35]
  R. Liu, K.T. Tan, Y. Gong, et al., Chem. Soc. Rev. 50 (2021) 120–242. doi: 10.1039/d0cs00620c
36. [36]
  K. Geng, T. He, R. Liu, et al., Chem. Rev. 120 (2020) 8814–8933. doi: 10.1021/acs.chemrev.9b00550
37. [37]
  P.J. Waller, F. Gándara, O.M. Yaghi, Acc. Chem. Res. 48 (2015) 3053–3063. doi: 10.1021/acs.accounts.5b00369
38. [38]
  P.J. Waller, F. Gándara, O.M. Yaghi, Acc. Chem. Res. 48 (2015) 3053–3063. doi: 10.1021/acs.accounts.5b00369
39. [39]
  X. Feng, X. Ding, D. Jiang, Chem. Soc. Rev. 41 (2012) 6010–6022. doi: 10.1039/c2cs35157a
40. [40]
  W. Liu, Q. Su, P. Ju, et al., ChemSusChem 10 (2017) 664–669. doi: 10.1002/cssc.201601702
41. [41]
  Y. Zhi, Z. Li, X. Feng, et al., J. Mater. Chem. A 5 (2017) 22933–22938. doi: 10.1039/C7TA07691F
42. [42]
  W. Huang, J. Byun, I. Rörich, et al., Angew. Chem. Int. Ed. 57 (2018) 8316–8320. doi: 10.1002/anie.201801112
43. [43]
  P.F. Wei, M.Z. Qi, Z.P. Wang, et al., J. Am. Chem. Soc. 140 (2018) 4623–4631. doi: 10.1021/jacs.8b00571
44. [44]
  M. Bhadra, S. Kandambeth, M.K. Sahoo, et al., J. Am. Chem. Soc. 141 (2019) 6152–6156. doi: 10.1021/jacs.9b01891
45. [45]
  R. Chen, J.L. Shi, Y. Ma, et al., Angew. Chem. Int. Ed. 58 (2019) 6430–6434. doi: 10.1002/anie.201902543
46. [46]
  W. Hao, D. Chen, Y. Li, et al., Chem. Mater. 31 (2019) 8100–8105. doi: 10.1021/acs.chemmater.9b02718
47. [47]
  S. Liu, W. Pan, S. Wu, et al., Green Chem. 21 (2019) 2905–2910. doi: 10.1039/c9gc00022d
48. [48]
  M. Tian, S. Liu, X. Bu, J. Yu, X. Yang, Chem. Eur. J. 26 (2020) 369–373. doi: 10.1002/chem.201903523
49. [49]
  Z. Almansaf, J. Hu, F. Zanca, et al., ACS Appl. Mater. Interfaces 13 (2021) 6349–6358. doi: 10.1021/acsami.0c21370
50. [50]
  Z. Liang, H. Guo, H. Lei, R. Cao, Chin. Chem. Lett. (2021), doi:10.1016/j.cclet.2021.11.055. doi: 10.1016/j.cclet.2021.11.055
51. [51]
  G. Jiang, X. Liu, H. Jian, et al., Chin. Chem. Lett. 33 (2022) 3049–3052. doi: 10.1016/j.cclet.2021.09.047
52. [52]
  H.K. Li, H.L. Ye, X.X. Zhao, et al., Chin. Chem. Lett. 32 (2021) 2851–2855. doi: 10.1016/j.cclet.2021.02.042
53. [53]
  Y. Hou, X. Zhang, J. Sun, et al., Microporous Mesoporous Mater. 214 (2015) 108–114. doi: 10.1016/j.micromeso.2015.05.002
54. [54]
  S. Lin, C.S. Diercks, Y.B. Zhang, et al., Science 349 (2015) 1208–1213. doi: 10.1126/science.aac8343
55. [55]
  N.J. Turro, V. Ramamurthy, J.C. Scaiano, Modern Molecular Photochemistry of Organic Molecules, University Science Books, Sausalito, CA, 2010, p. 252. doi: 10.1111/j.1751-1097.2012.01178.x
56. [56]
  W. Huang, Z.J. Wang, B.C. Ma, et al., J. Mater. Chem. A 4 (2016) 7555–7559. doi: 10.1039/C6TA01828A
57. [57]
  W. Huang, B.C. Ma, H. Lu, et al., ACS Catal. 7 (2017) 5438–5442. doi: 10.1021/acscatal.7b01719
58. [58]
  M. Silvi, C. Verrier, Y.P. Rey, L. Buzzetti, P. Melchiorre, Nat. Chem. 9 (2017) 868–873. doi: 10.1038/nchem.2748
59. [59]
  H.G. Roth, N.A. Romero, D.A. Nicewicz, Synlett 27 (2016) 714–723.
60. [60]
  N.G. Connelly, W.E. Geiger, Chem. Rev. 96 (1996) 877–910. doi: 10.1021/CR940053X
1. [1]
  Jiangqi Ning , Junhan Huang , Yuhang Liu , Yanlei Chen , Qing Niu , Qingqing Lin , Yajun He , Zheyuan Liu , Yan Yu , Liuyi Li . Alkyl-linked TiO2@COF heterostructure facilitating photocatalytic CO2 reduction by targeted electron transport. Chinese Journal of Structural Chemistry, 2024, 43(12): 100453-100453. doi: 10.1016/j.cjsc.2024.100453
2. [2]
  Chen Lu , Zefeng Yu , Jing Cao . Advancement in porphyrin/phthalocyanine compounds-based perovskite solar cells. Chinese Journal of Structural Chemistry, 2024, 43(3): 100240-100240. doi: 10.1016/j.cjsc.2024.100240
3. [3]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
4. [4]
  Yinyin Xu , Yuanyuan Li , Jingbo Feng , Chen Wang , Yan Zhang , Yukun Wang , Xiuwen Cheng . Covalent organic frameworks doped with manganese-metal organic framework for peroxymonosulfate activation. Chinese Chemical Letters, 2024, 35(4): 108838-. doi: 10.1016/j.cclet.2023.108838
5. [5]
  Chao Liu , Chao Jia , Shi-Xian Gan , Qiao-Yan Qi , Guo-Fang Jiang , Xin Zhao . A luminescent one-dimensional covalent organic framework for organic arsenic sensing in water. Chinese Chemical Letters, 2024, 35(11): 109750-. doi: 10.1016/j.cclet.2024.109750
6. [6]
  Yihao Zhang , Yang Jiao , Xianchao Jia , Qiaojia Guo , Chunying Duan . Highly effective self-assembled porphyrin MOCs nanomaterials for enhanced photodynamic therapy in tumor. Chinese Chemical Letters, 2024, 35(5): 108748-. doi: 10.1016/j.cclet.2023.108748
7. [7]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
8. [8]
  Yunyu Zhao , Chuntao Yang , Yingjian Yu . A review on covalent organic frameworks for rechargeable zinc-ion batteries. Chinese Chemical Letters, 2024, 35(7): 108865-. doi: 10.1016/j.cclet.2023.108865
9. [9]
  Xinyi Cao , Yucheng Jin , Hailong Wang , Xu Ding , Xiaolin Liu , Baoqiu Yu , Xiaoning Zhan , Jianzhuang Jiang . A tetraaldehyde-derived porous organic cage and covalent organic frameworks: Syntheses, structures, and iodine vapor capture. Chinese Chemical Letters, 2024, 35(9): 109201-. doi: 10.1016/j.cclet.2023.109201
10. [10]
  Yuqing Wang , Zhemin Li , Qingjun Lu , Qizhao Li , Jiaxin Luo , Chengjie Li , Yongshu Xie . Solar cells based on doubly concerted companion dyes with the efficiencies modulated by inserting an ethynyl group at different positions. Chinese Chemical Letters, 2024, 35(5): 109093-. doi: 10.1016/j.cclet.2023.109093
11. [11]
  Weixu Li , Yuexin Wang , Lin Li , Xinyi Huang , Mengdi Liu , Bo Gui , Xianjun Lang , Cheng Wang . Promoting energy transfer pathway in porphyrin-based sp2 carbon-conjugated covalent organic frameworks for selective photocatalytic oxidation of sulfide. Chinese Journal of Structural Chemistry, 2024, 43(7): 100299-100299. doi: 10.1016/j.cjsc.2024.100299
12. [12]
  Fei Xie , Chengcheng Yuan , Haiyan Tan , Alireza Z. Moshfegh , Bicheng Zhu , Jiaguo Yu . d带中心调控过渡金属单原子负载COF吸附O₂的理论计算研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2407013-. doi: 10.3866/PKU.WHXB202407013
13. [13]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
14. [14]
  Jindian Duan , Xiaojuan Ding , Pui Ying Choy , Binyan Xu , Luchao Li , Hong Qin , Zheng Fang , Fuk Yee Kwong , Kai Guo . Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway. Chinese Chemical Letters, 2024, 35(10): 109565-. doi: 10.1016/j.cclet.2024.109565
15. [15]
  Xingyan Liu , Chaogang Jia , Guangmei Jiang , Chenghua Zhang , Mingzuo Chen , Xiaofei Zhao , Xiaocheng Zhang , Min Fu , Siqi Li , Jie Wu , Yiming Jia , Youzhou He . Single-atom Pd anchored in the porphyrin-center of ultrathin 2D-MOFs as the active center to enhance photocatalytic hydrogen-evolution and NO-removal. Chinese Chemical Letters, 2024, 35(9): 109455-. doi: 10.1016/j.cclet.2023.109455
16. [16]
  Jiaqi Ma , Lan Li , Yiming Zhang , Jinjie Qian , Xusheng Wang . Covalent organic frameworks: Synthesis, structures, characterizations and progress of photocatalytic reduction of CO2. Chinese Journal of Structural Chemistry, 2024, 43(12): 100466-100466. doi: 10.1016/j.cjsc.2024.100466
17. [17]
  Kun Tang , Yu-Wu Zhong . Water reduction by an organic single-chromophore photocatalyst. Chinese Journal of Structural Chemistry, 2024, 43(8): 100376-100376. doi: 10.1016/j.cjsc.2024.100376
18. [18]
  Guorong Li , Yijing Wu , Chao Zhong , Yixin Yang , Zian Lin . Predesigned covalent organic framework with sulfur coordination: Anchoring Au nanoparticles for sensitive colorimetric detection of Hg(Ⅱ). Chinese Chemical Letters, 2024, 35(5): 108904-. doi: 10.1016/j.cclet.2023.108904
19. [19]
  Yue Qian , Zhoujia Liu , Haixin Song , Ruize Yin , Hanni Yang , Siyang Li , Weiwei Xiong , Saisai Yuan , Junhao Zhang , Huan Pang . Imide-based covalent organic framework with excellent cyclability as an anode material for lithium-ion battery. Chinese Chemical Letters, 2024, 35(6): 108785-. doi: 10.1016/j.cclet.2023.108785
20. [20]
  Yuting Wu , Haifeng Lv , Xiaojun Wu . Design of two-dimensional porous covalent organic framework semiconductors for visible-light-driven overall water splitting: A theoretical perspective. Chinese Journal of Structural Chemistry, 2024, 43(11): 100375-100375. doi: 10.1016/j.cjsc.2024.100375

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(552)
HTML views(100)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142