Citation: Chen Yaqi, Gui Xin, Duan Zunbin, Zhu Lijun, Xiang Yuzhi, Xia Daohong. Transition Metal Catalyzed Organic Reaction Involving Cyclodextrin[J]. Chinese Journal of Organic Chemistry, ;2019, 39(5): 1284-1292. doi: 10.6023/cjoc201809012 shu

Transition Metal Catalyzed Organic Reaction Involving Cyclodextrin

State Key Laboratory of Heavy Oil Processing, College of Chemical Engineering, China University of Petroleum(East China), Qingdao 266580

Corresponding author: Xia Daohong, xiadh@upc.edu.cn
Received Date: 6 September 2018
Revised Date: 3 December 2018
Available Online: 18 May 2019
Fund Project: the the National Natural Science Foundation of China 21376265Project supported by the the National Natural Science Foundation of China (No. 21376265)

Figures(10)

Cyclodextrin is a kind of cyclic oligosaccharide which is composed of the D-pyran glucose units connected with the α-1, 4-glycosidic bond. Cyclodextrin has the rigidly tapered cavity of hydrophobic inner and hydrophilic outer. Cyclodextrin has been attracted more and more attention from scientists since it was discovered, owning to its special space cavity of hydrophilic inner and hydrophilic outer. As an important industrial catalyst, transition metal catalyst can combine with the cyclodextrin system to simultaneously exert the catalytic properties of the metal and the molecular recognition and phase transfer of cyclodextrin, which greatly improves its catalytic performance. In this paper, the transition metal catalyzed organic reactions involving cyclodextrin are reviewed, and these reactions are described in terms of the metal valence from 0 to 4. Finally, the development and foreground of these co-catalyst systems involving metal and cyclodextrin are prospected. It is expected that the catalytic system will have a wider application in the future, and a more efficient and selective catalytic system will be continuously developed.
- cyclodextrin,
- transition metal,
- catalysis,
- reaction,
- synthesis,
- complexes
1. [1]
  Lai, E.; Jean, M.; Shen, X. H. M. Supramolecular Chemistry:Concepts and Prospects, Peking University Press, Beijing, 2002 (in Chinese).
2. [2]
  Xia, D. H.; Jiang, S. J.; Li, L.-L.; Xiang, Y. Z.; Zhu, L. J. Chin. J. Chem. Eng. 2016, 24, 146. doi: 10.1016/j.cjche.2015.06.008
3. [3]
  Tong, L. H. M. Cyclodextrin Chemistry-Basics and Applications, Science Press, Beijing, 2001 (in Chinese).
4. [4]
  Shen, H. M.; Ji, H. B. Chin. J. Org. Chem. 2011, 32, 791(in Chinese),
5. [5]
  Zhao, Y.; Huang, Y.; Zhu, H.; Zhu, Q.; Xia, Y. J. Am. Chem. Soc. 2016, 138, 16645. doi: 10.1021/jacs.6b07590
6. [6]
  Menuel, S.; Léger, B.; Addad, A.; Monflier, E.; Hapiot, F. Green Chem. 2016, 18, 5500. doi: 10.1039/C6GC00770H
7. [7]
  Stewart, M. E.; Anderton, C. R.; Thompson, L. B.; Maria, J.; Gray, S. K.; Rogers, J.A.; Nuzzo, R. G. Chem. Rev. 2008, 108, 494. doi: 10.1021/cr068126n
8. [8]
  Xiao, J.; Qi, L. Nanoscale 2011, 3, 1383. doi: 10.1039/c0nr00814a
9. [9]
  Shanmugam, M.; Kim, K. J. Electroanal. Chem. 2016, 776, 82. doi: 10.1016/j.jelechem.2016.06.009
10. [10]
  Cravotto, G.; Gaudino, E. C.; Tagliapietra, S.; Carnaroglio, D.; Procopio, A. Green Proc. Synth. 2012, 1, 269.
11. [11]
  Hein, J. E.; Tripp, J. C.; Krasnova, L. B.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2009, 48, 8018. doi: 10.1002/anie.v48:43
12. [12]
  Dheer, D.; Rawal, R. K.; Singh, V.; Sangwan, P. L.; Das, P.; Shankar, R. Tetrahedron 2017, 73, 4295. doi: 10.1016/j.tet.2017.05.081
13. [13]
  Patil, R. N.; Vijay Kumar, A. ACS Omega 2017, 2, 6405. doi: 10.1021/acsomega.7b00898
14. [14]
  Messmer, E. Z. Phys. Chem. 1927, 126, 369.
15. [15]
  Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 113, 2056. doi: 10.1002/(ISSN)1521-3757
16. [16]
  Krasinski, A.; Radic, Z.; Manetsch, R.; Raushel, J.; Taylor, P.; Sharpless, K. B.; Kolb, H. C. J. Am. Chem. Soc. 2004, 126, 12809. doi: 10.1021/ja046382g
17. [17]
  Hein, J. E.; Tripp, J. P.; Krasnova, L. B.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2009, 48, 1. doi: 10.1002/anie.200890275
18. [18]
  Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596. doi: 10.1002/(ISSN)1521-3773
19. [19]
  Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057. doi: 10.1021/jo011148j
20. [20]
  Aprahamian, I.; Dichtel, W. R.; Ikeda, T.; Heath, J. R.; Stoddart, J. F. Org. Lett. 2007, 9, 1287. doi: 10.1021/ol070052u
21. [21]
  Yigit, S.; Sanyal, R.; Sanyal, A. Chem. Asian J. 2011, 6, 2648. doi: 10.1002/asia.v6.10
22. [22]
  Yamada, Y. M. A.; Sarkar, S. M.; Uozumi, Y. J. Am. Chem. Soc. 2012, 134, 9285. doi: 10.1021/ja3036543
23. [23]
  Collinson, J.-M.; Wilton-Ely, J. D. E. T.; Diez-Gonzalez, S. Chem. Commun. 2013, 49, 11358. doi: 10.1039/c3cc44371j
24. [24]
  Xiong, X.; Chen, H.; Tang, Z.; Jiang, Y. RSC Adv. 2014, 4, 9830. doi: 10.1039/c3ra45994b
25. [25]
  White, J. R.; Price, G. J.; Schiffers, S.; Raithby, P. R.; Plucinski, P. K.; Frost, C. G. Tetrahedron Lett. 2010, 51, 3913. doi: 10.1016/j.tetlet.2010.05.104
26. [26]
  Brotherton, W. S.; Michaels, H. A.; Simmons, J. T.; Clark, R. J.; Dalal, N. S.; Zhu, L. Org. Lett. 2009, 11, 4954. doi: 10.1021/ol9021113
27. [27]
  Hein, J. E.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1302. doi: 10.1039/b904091a
28. [28]
  Zhu, L.; Lynch, V. M.; Ansly, E. V. Tetrahedron 2004, 60, 7267. doi: 10.1016/j.tet.2004.06.079
29. [29]
  Zhang, H.; Tanimoto, H.; Morimoto, T.; Nishiyama, Y.; Kakiuchi, K. Tetrahedron 2014, 70, 9828. doi: 10.1016/j.tet.2014.10.076
30. [30]
  Ramesh, C.; Banerjee, J.; Pal, R.; Das, B. Adv. Synth. Catal. 2003, 345, 557. doi: 10.1002/adsc.200303022
31. [31]
  Sheng, S. R.; Wang, Q. Y.; Ding, Y.; Liu, X. L.; Cai, M. Z. Catal Lett. 2009, 128, 418. doi: 10.1007/s10562-008-9767-z
32. [32]
  Reddi, M. N. K.; Satheesh, K. B.; Anil, K. M.; Arulselvan, P.; Ibrahim, K. S.; Lasekan, O. Molecules 2012, 17, 7543. doi: 10.3390/molecules17067543
33. [33]
  Ramesh, C.; Banerjee, J.; Pal, R.; Das, B. ChemInform 2010, 345, 557.
34. [34]
  Dabbawala, A. A.; Sudheesh, N.; Bajaj, H. C. Dalton. Trans. 2012, 41, 2910. doi: 10.1039/c2dt11924b
35. [35]
  Datta, K. K. R.; Srinivasan, B.; Balaram, H.; Eswaramoorthy, M. J Chem. Sci. 2008, 120, 579. doi: 10.1007/s12039-008-0088-y
36. [36]
  Nie, R.; Sang, R.; Ma, X.; Zheng, Y.; Cheng, X.; Li, W.; Wu, Y. J. Catal. 2016, 344, 286. doi: 10.1016/j.jcat.2016.09.022
37. [37]
  Yao, Z.; Hong, S.; Zhang, W.; Liu, M.; Deng, W. Tetrahedron Lett. 2016, 57, 910. doi: 10.1016/j.tetlet.2016.01.049
38. [38]
  Zhang, P.; Meijide, S. J.; Driant, T.; Derat, E.; Zhang, Y.; Ménand, M. Angew. Chem. 2017, 129, 10961. doi: 10.1002/ange.201705303
39. [39]
  (a) Kaboudin, B.; Abedi, Y.; Yokomatsu, T. Eur. J. Org. Chem. 2011, 6656.
  (b) Kaboudin, B.; Abedi, Y.; Yokomatsu, T. Org. Biomol. Chem. 2012, 10, 4543.
40. [40]
  Kaboudin, B.; Mostafalu, R.; Yokomatsu, T. ChemInform 2013, 44, 2262.
41. [41]
  Perez, A. L.; Moseguer, J. O.; Marques, P. R.; Corma, A. Angew. Chem., Int. Ed. 2013, 125, 11768. doi: 10.1002/ange.201303188
42. [42]
  Hoffmann, I.; Blumenröder, B.; Thumann, S. O. N.; Dommer, S.; Schatz, J. Green Chem. 2015, 17, 3844. doi: 10.1039/C5GC00794A
43. [43]
  Saito, N.; Taniguchi, T.; Hoshiya, N.; Shuto, S.; Arisawa, M.; Sato, Y. Green Chem. 2015, 17, 2358. doi: 10.1039/C4GC02469A
44. [44]
  (a) Zhong, R.; Pöthig, A.; Feng, Y.; Riener, K.; Herrmann, W. A.; Kühn, F. E. Green Chem. 2014, 16, 4955.
  (b) Billingsley, K.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 38, 3358.
  (c) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 30, 4369.
  (d) Martin R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461.
  (e) Vellakkaran, M.; Andappan, M. M. S.; Kommu, N. Green Chem. 2014, 16, 2788.
45. [45]
  Raihana, I. K.; Kasi, P. Green Chem. 2016, 18, 4791. doi: 10.1039/C6GC90091G
46. [46]
  Qi, M.; Tan, P. Z. Xue, F.; Malhi, H. S.; Zhang, Z. X.; Young, D. J. Rsc. Adv. 2014, 5, 3590.
47. [47]
  Zhou, X.; Guo, X.; Jian, F.; Wei, G. ACS Omega 2018, 3, 4418. doi: 10.1021/acsomega.8b00469
48. [48]
  Guo, Y.; Li, J.; Zhao, F.; Lan, G.; Li, L.; Liu, Y.; Yang, R. RSC Adv. 2016, 6, 7950. doi: 10.1039/C5RA23271F
49. [49]
  Imran, K. R.; Pitchumani, K. ACS Sustainable Chem. Eng, 2018.
50. [50]
  Poulos, T. L. Chem. Rev. 2014, 114, 3919. doi: 10.1021/cr400415k
51. [51]
  Sreenilayam, G.; Fasan, R. Chem. Commun. 2015, 51, 1532. doi: 10.1039/C4CC08753D
52. [52]
  Xu, X.; Li, C.; Tao, Z.; Pan, Y. Adv. Synth. Catal. 2015, 357, 3341. doi: 10.1002/adsc.201500418
53. [53]
  Wang, M. L.; Fang, G. D; Liu, P. Appl. Catal., B 2016, 188, 113. doi: 10.1016/j.apcatb.2016.01.071
54. [54]
  Guo, Y.; Guo, S.; Ren, J.; Zhai, Y.; Dong, S.; Wang, E. ACS Nano. 2010, 4, 4001. doi: 10.1021/nn100939n
55. [55]
  Sharavath, V.; Sarkar, S.; Gandla, D.; Ghosh, S. Electrochim. Acta 2016, 210, 385. doi: 10.1016/j.electacta.2016.05.177
56. [56]
  Mohamed, M. A.; Shukla, A.; Sandhya, K. Y. Environ. Prog. Sustainable 2016, 35, 1283. doi: 10.1002/ep.v35.5
57. [57]
  Subramanian, R.; Ponnusamy, V. J. Mater. Sci.: Mater. Electron. 2016, 28, 1.
58. [58]
  Sun, N.; Wang, T.; Liu, C. Wood. Sci. Tenol. 2016, 50, 1. doi: 10.1007/s00226-015-0797-6
1. [1]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
2. [2]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
3. [3]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
4. [4]
  Xuyu WANG , Xinran XIE , Dengke CAO . Photoreaction characteristics and luminescence modulation in phosphine-anthracene-based Au(Ⅰ) and Ir(Ⅲ) complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1513-1522. doi: 10.11862/CJIC.20250113
5. [5]
  Yan Qi , Yueqin Yu , Weisi Guo , Yongjun Liu . 过渡金属参与的有机反应案例教学与实践探索. University Chemistry, 2025, 40(6): 111-117. doi: 10.12461/PKU.DXHX202411021
6. [6]
  Zuozhong Liang , Lingling Wei , Yiwen Cao , Yunhan Wei , Haimei Shi , Haoquan Zheng , Shengli Gao . Exploring the Development of Undergraduate Scientific Research Ability in Basic Course Instruction: A Case Study of Alkali and Alkaline Earth Metal Complexes in Inorganic Chemistry. University Chemistry, 2024, 39(7): 247-263. doi: 10.3866/PKU.DXHX202310103
7. [7]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
8. [8]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
9. [9]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
10. [10]
  Xiaotong LU , Pan ZHANG , Zijie ZHAO , Lei HUANG , Hongwei ZUO , Lili LIANG . Antitumor and antibacterial activities of pyridyl Schiff base indium and dysprosium complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1523-1532. doi: 10.11862/CJIC.20250073
11. [11]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . Catalytic Effect of H₃PW₁₂O₄₀ on Hydrogen Storage of MgH₂. Acta Physico-Chimica Sinica, 2025, 41(1): 100001-0. doi: 10.3866/PKU.WHXB202308032
12. [12]
  Xiaogang Liu , Mengyu Chen , Yanyan Li , Xiantao Ma . Experimental Reform in Applied Chemistry for Cultivating Innovative Competence: A Case Study of Catalytic Hydrogen Production from Liquid Formaldehyde Reforming at Room Temperature. University Chemistry, 2025, 40(7): 300-307. doi: 10.12461/PKU.DXHX202408007
13. [13]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
14. [14]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
15. [15]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
16. [16]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
17. [17]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
18. [18]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
19. [19]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
20. [20]
  Jiaxun Wu , Mingde Li , Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098

Get Citation

PDF

XML

Metrics

PDF Downloads(19)
Abstract views(2118)
HTML views(539)

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