Citation: Yu-Feng Liu, Chang-Wen Hu, Guo-Ping Yang. Recent advances in polyoxometalates acid-catalyzed organic reactions[J]. Chinese Chemical Letters, ;2023, 34(5): 108097. doi: 10.1016/j.cclet.2022.108097 shu

Recent advances in polyoxometalates acid-catalyzed organic reactions

Yu-Feng Liu ^a ,
Chang-Wen Hu ^{b, *,} ,
Guo-Ping Yang ^{a, *,}

a.
Jiangxi Province Key Laboratory of Synthetic Chemistry, Jiangxi Key Laboratory for Mass Spectrometry and Instrumentation, East China University of Technology, Nanchang 330013, China
b.
Key Laboratory of Cluster Science of Ministry of Education, Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, China

cwhu@bit.edu.cn

erick@ecut.edu.cn

Received Date: 19 October 2022
Revised Date: 10 November 2022
Accepted Date: 22 December 2022
Available Online: 24 December 2022

Figures(33)

Polyoxometalates (POMs) have conducive properties such as controlled Brønsted and Lewis acidity, high thermal stability, nontoxic nature, tunable solubility, and less corrosiveness. POMs have been extensively applied in catalytic organic reactions and have an exciting prospect for industrial applications. This review summarized recent progress in the application of POMs as acid catalysts for various organic reactions including CC bond formation, CN bond formation, CO bond formation, heterocyclic synthesis reactions, cyanosilylation and hydrolysis reactions. Various POMs catalysts including heteropoly acids (HPAs) and cationic functionalized HPAs with Brønsted acidity, HPAs supported on non-precious metal support with Brønsted acidity (or both Brønsted and Lewis acidity), transition metal substituted POMs with Lewis acidity were applied in above reactions. This review attempts to provide up-to-date information about POMs acid-catalyzed organic reactions and propose future prospects.
- Polyoxometalates,
- Acid catalysis,
- CC bond formation,
- CN bond formation,
- CO bond formation,
- Heterocyclic synthesis,
- Cyanosilylation and hydrolysis reactions
1. [1]
  A. Bijelic, A. Rompel, Coord. Chem. Rev. 299 (2015) 22–38. doi: 10.1016/j.ccr.2015.03.018
2. [2]
  B. Chakraborty, I.A. Weinstock, Coord. Chem. Rev. 382 (2019) 85–102. doi: 10.1016/j.ccr.2018.11.011
3. [3]
  X.X. Li, D. Zhao, S.T. Zheng, Coord. Chem. Rev. 397 (2019) 220–240. doi: 10.1016/j.ccr.2019.07.005
4. [4]
  H. Lv, Y.V. Geletii, C. Zhao, et al., Chem. Soc. Rev. 41 (2012) 7572–7589. doi: 10.1039/c2cs35292c
5. [5]
  N. Mizuno, K. Kamata, Coord. Chem. Rev. 255 (2011) 2358–2370. doi: 10.1016/j.ccr.2011.01.041
6. [6]
  N. Narkhede, S. Singh, A. Patel, Green Chem. 17 (2015) 89–107. doi: 10.1039/C4GC01743A
7. [7]
  C. Yvon, A.J. Surman, M. Hutin, et al., Angew. Chem. Int. Ed. 53 (2014) 3336–3341. doi: 10.1002/anie.201311135
8. [8]
  H.Y. Zhao, Y.Z. Li, J.W. Zhao, et al., Coord. Chem. Rev. 443 (2021) 213966. doi: 10.1016/j.ccr.2021.213966
9. [9]
  S.T. Zheng, G.Y. Yang, Chem. Soc. Rev. 41 (2012) 7623–7646. doi: 10.1039/c2cs35133a
10. [10]
  D.L. Long, E. Burkholder, L. Cronin, Chem. Soc. Rev. 36 (2007) 105–121. doi: 10.1039/B502666K
11. [11]
  D.L. Long, R. Tsunashima, L. Cronin, Angew. Chem. Int. Ed. 49 (2010) 1736–1758. doi: 10.1002/anie.200902483
12. [12]
  L. Chen, W.L. Chen, X.L. Wang, et al., Chem. Soc. Rev. 48 (2019) 260–284. doi: 10.1039/c8cs00559a
13. [13]
  D.Y. Du, J.S. Qin, S.L. Li, et al., Chem. Soc. Rev. 43 (2014) 4615–4632. doi: 10.1039/C3CS60404G
14. [14]
  W.H. Fang, L. Zhang, J. Zhang, Chem. Soc. Rev. 47 (2018) 404–421. doi: 10.1039/C7CS00511C
15. [15]
  I.A. Weinstock, R.E. Schreiber, R. Neumann, Chem. Rev. 118 (2018) 2680–2717. doi: 10.1021/acs.chemrev.7b00444
16. [16]
  J. Zhang, Y. Huang, G. Li, et al., Coord. Chem. Rev. 378 (2019) 395–414. doi: 10.1016/j.ccr.2017.10.025
17. [17]
  D.J. Zang, H.Q. Wang, Polyoxometalates 1 (2022) 9140006. doi: 10.26599/pom.2022.9140006
18. [18]
  N.S. Bhat, S.S. Mal, S. Dutta, Mol. Catal. 505 (2021) 111484. doi: 10.1016/j.mcat.2021.111484
19. [19]
  I.V. Kozhevnikov, J. Mol. Catal. A: Chem. 262 (2007) 86–92. doi: 10.1016/j.molcata.2006.08.072
20. [20]
  L. Lian, H. Zhang, S. An, et al., Sci. China Chem. 64 (2021) 1117–1130. doi: 10.1007/s11426-020-9957-0
21. [21]
  S.S. Wang, G.Y. Yang, Chem. Rev. 115 (2015) 4893–4962. doi: 10.1021/cr500390v
22. [22]
  M.M. Heravi, S. Sadjadi, J. Iran. Chem. Soc. 6 (2009) 1–54.
23. [23]
  Y. Leng, J. Wang, D. Zhu, et al., Angew. Chem. Int. Ed. 48 (2009) 168–171. doi: 10.1002/anie.200803567
24. [24]
  Z.Y. Liu, Y.D. Lin, Y. Hao, et al., Tungsten 4 (2022) 81–98. doi: 10.1007/s42864-021-00134-1
25. [25]
  N. Mizuno, K. Yamaguchi, K. Kamata, Coord. Chem. Rev. 249 (2005) 1944–1956. doi: 10.1016/j.ccr.2004.11.019
26. [26]
  P.G. Romanelli, C.J. Autino, Mini-Rev. Org. Chem. 6 (2009) 359–366. doi: 10.2174/157019309789371578
27. [27]
  J. Zhong, J. Pérez-Ramírez, N. Yan, Green Chem. 23 (2021) 18–36. doi: 10.1039/d0gc03190a
28. [28]
  X. Huang, N. Zhen, Y. Chi, et al., Sci. Sin. Chim. 50 (2020) 1064. doi: 10.1360/SSC-2020-0083
29. [29]
  I.V. Kozhevnikov, Chem. Rev. 98 (1998) 171–198. doi: 10.1021/cr960400y
30. [30]
  E. Ahmad, T.S. Khan, M.I. Alam, et al., Chem. Eng. J. 400 (2020) 125916. doi: 10.1016/j.cej.2020.125916
31. [31]
  Y. Chen, D. Liu, R. Wang, et al., J. Org. Chem. 87 (2022) 351–362. doi: 10.1021/acs.joc.1c02385
32. [32]
  F. de Azambuja, J. Lenie, T.N. Parac-Vogt, ACS Catal. 11 (2021) 271–277. doi: 10.1021/acscatal.0c04189
33. [33]
  F. de Azambuja, T.N. Parac-Vogt, ACS Catal. 9 (2019) 10245–10252. doi: 10.1021/acscatal.9b03415
34. [34]
  J. Li, S. Zhao, Z. Li, et al., Inorg. Chem. 60 (2021) 7785–7793. doi: 10.1021/acs.inorgchem.1c00185
35. [35]
  J. Yang, M.J. Janik, D. Ma, et al., J. Am. Chem. Soc. 127 (2005) 18274–18280. doi: 10.1021/ja055925z
36. [36]
  N. Mizuno, M. Misono, Chem. Rev. 98 (1998) 199–218. doi: 10.1021/cr960401q
37. [37]
  W. Deng, Q. Zhang, Y. Wang, Dalton Trans. 41 (2012) 9817–9831. doi: 10.1039/c2dt30637a
38. [38]
  Z. Wei, J. Wang, H. Yu, et al., Molecules 27 (2022) 5212–5225. doi: 10.3390/molecules27165212
39. [39]
  I.V. Kozhevnikov, Appl. Catal. A: Gen. 256 (2003) 3–18. doi: 10.1016/S0926-860X(03)00406-X
40. [40]
  H. Li, C.C.C. Johansson Seechurn, T.J. Colacot, ACS Catal. 2 (2012) 1147–1164. doi: 10.1021/cs300082f
41. [41]
  X.F. Wu, P. Anbarasan, H. Neumann, et al., Angew. Chem. Int. Ed. 49 (2010) 9047–9050. doi: 10.1002/anie.201006374
42. [42]
  K.R. Holman, A.M. Stanko, S.E. Reisman, Chem. Soc. Rev. 50 (2021) 7891–7908. doi: 10.1039/d0cs01385d
43. [43]
  C.S. Wang, P.H. Dixneuf, J.F. Soulé, Chem. Rev. 118 (2018) 7532–7585. doi: 10.1021/acs.chemrev.8b00077
44. [44]
  L.E. Zetzsche, A.R.H. Narayan, Nat. Rev. Chem. 4 (2020) 334–346. doi: 10.1038/s41570-020-0191-2
45. [45]
  T. Ueda, K. Yamashita, A. Onda, Appl. Catal. A: Gen. 485 (2014) 181–187. doi: 10.1016/j.apcata.2014.07.032
46. [46]
  G.P. Yang, Y.F. Liu, K. Li, et al., Chin. Chem. Lett. 31 (2020) 3233–3236. doi: 10.1016/j.cclet.2020.07.018
47. [47]
  G.P. Yang, D. Dilixiati, T. Yang, et al., Appl. Organomet. Chem. 32 (2018) e4450. doi: 10.1002/aoc.4450
48. [48]
  J. Li, Y. Zhou, D. Mao, et al., Chem. Eng. J. 254 (2014) 54–62. doi: 10.21273/jashs.139.1.54
49. [49]
  E. Rafiee, F. Mirnezami, M. Kahrizi, J. Mol. Struct. 1119 (2016) 332–339. doi: 10.1016/j.molstruc.2016.04.098
50. [50]
  D.N.K. Reddy, K.B. Chandrasekhar, Y.S.S. Ganesh, et al., Synth. Commun. 45 (2015) 513–523. doi: 10.1080/00397911.2014.966392
51. [51]
  M. Ammar, S. Jiang, S. Ji, J. Solid State Chem. 233 (2016) 303–310. doi: 10.1016/j.jssc.2015.11.014
52. [52]
  L. Ullah, G. Zhao, Z. Xu, et al., Sci. China Chem. 61 (2018) 402–411. doi: 10.1007/s11426-017-9182-0
53. [53]
  C. Pezzotta, G. Fleury, M. Soetens, et al., J. Catal. 359 (2018) 198–211. doi: 10.1016/j.jcat.2018.01.010
54. [54]
  M.S. Rahaman, S. Tulaphol, M.A. Hossain, et al., Mol. Catal. 514 (2021) 111848. doi: 10.1016/j.mcat.2021.111848
55. [55]
  G.P. Yang, N. Zhang, N.N. Ma, et al., Adv. Synth. Catal. 359 (2017) 926–932. doi: 10.1002/adsc.201601231
56. [56]
  G.P. Yang, N. Jiang, X.Q. Huang, et al., Mol. Catal. 468 (2019) 80–85. doi: 10.1016/j.mcat.2019.02.019
57. [57]
  G.P. Yang, X. Wu, B. Yu, et al., ACS Sustainable Chem. Eng. 7 (2019) 3727–3732. doi: 10.1021/acssuschemeng.8b06445
58. [58]
  Z. Hui, S. Jiang, X. Qi, et al., Tetrahedron Lett. 61 (2020) 151995. doi: 10.1016/j.tetlet.2020.151995
59. [59]
  M.R. Becker, R.B. Watson, C.S. Schindler, Chem. Soc. Rev. 47 (2018) 7867–7881. doi: 10.1039/c8cs00391b
60. [60]
  J. Macht, M.J. Janik, M. Neurock, et al., J. Am. Chem. Soc. 130 (2008) 10369–10379. doi: 10.1021/ja803114r
61. [61]
  A.R.C. Morais, S. Dworakowska, A. Reis, et al., Catal. Today 239 (2015) 38–43. doi: 10.1016/j.cattod.2014.05.033
62. [62]
  V.L. Sushkevich, V.V. Ordomsky, I.I. Ivanova, Catal. Sci. Technol. 6 (2016) 6354–6364. doi: 10.1039/C6CY00761A
63. [63]
  S. Wang, E. Iglesia, ACS Catal. 6 (2016) 7664–7684. doi: 10.1021/acscatal.6b02171
64. [64]
  P.A. Kots, M.A. Artsiusheuski, Y.V. Grigoriev, et al., ACS Catal. 10 (2020) 15149–15161. doi: 10.1021/acscatal.0c03282
65. [65]
  T. Ma, J. Ding, R. Shao, et al., Chem. Eng. J. 316 (2017) 797–806. doi: 10.1016/j.cej.2017.02.018
66. [66]
  R. Himmelmann, E. Klemm, M. Dyballa, Catal. Sci. Technol. 11 (2021) 3098–3108. doi: 10.1039/d1cy00143d
67. [67]
  A. Micek-Ilnicka, N. Ogrodowicz, U. Filek, et al., Catal. Today 380 (2021) 84–92. doi: 10.1016/j.cattod.2021.04.021
68. [68]
  T. Kella, A.A. Vennathan, S. Dutta, et al., Mol. Catal. 516 (2021) 111975. doi: 10.1016/j.mcat.2021.111975
69. [69]
  T.H. Kang, J.H. Choi, Y. Bang, et al., J. Mol. Catal. A: Chem. 396 (2015) 282–289. doi: 10.1016/j.molcata.2014.10.015
70. [70]
  M.J. West, J.W.B. Fyfe, J.C. Vantourout, et al., Chem. Rev. 119 (2019) 12491–12523. doi: 10.1021/acs.chemrev.9b00491
71. [71]
  Y. Zhao, W. Xia, Chem. Soc. Rev. 47 (2018) 2591–2608. doi: 10.1039/C7CS00572E
72. [72]
  G.W. Wang, Y.B. Shen, X.L. Wu, Eur. J. Org. Chem. 2008 (2008) 4367–4371. doi: 10.1002/ejoc.200800413
73. [73]
  M.A. Tzani, S. Fountoulaki, I.N. Lykakis, J. Org. Chem. 87 (2022) 2601–2615. doi: 10.1021/acs.joc.1c02550
74. [74]
  R.M. de Figueiredo, J.S. Suppo, J.M. Campagne, Chem. Rev. 116 (2016) 12029–12122. doi: 10.1021/acs.chemrev.6b00237
75. [75]
  V.R. Pattabiraman, J.W. Bode, Nature 480 (2011) 471–479. doi: 10.1038/nature10702
76. [76]
  C. Bougheloum, S. Alioua, R. Belghiche, et al., J. Heterocyclic. Chem. 57 (2020) 120–131. doi: 10.1002/jhet.3753
77. [77]
  R. Fu, Y. Yang, Y. Ma, et al., Tetrahedron Lett. 56 (2015) 4527–4531. doi: 10.1016/j.tetlet.2015.05.118
78. [78]
  M. Kooti, E. Nasiri, J. Mol. Catal. A: Chem. 406 (2015) 168–177. doi: 10.1016/j.molcata.2015.05.009
79. [79]
  A. Wang, Y. Xie, J. Wang, et al., Chem. Commun. 58 (2022) 1127–1130. doi: 10.1039/d1cc05417a
80. [80]
  P.J. Borpatra, B. Deka, M.L. Deb, et al., Org. Chem. Front. 6 (2019) 3445–3489. doi: 10.1039/c9qo00863b
81. [81]
  J. Le Bras, J. Muzart, Chem. Soc. Rev. 43 (2014) 3003–3040. doi: 10.1039/C3CS60379B
82. [82]
  J. Li, D. Li, J. Xie, et al., J. Catal. 339 (2016) 123–134. doi: 10.1016/j.jcat.2016.03.036
83. [83]
  L. Lian, X. Chen, X. Yi, et al., Chem. Eur. J. 26 (2020) 11900–11908. doi: 10.1002/chem.202001451
84. [84]
  R.S. Malkar, H. Daly, C. Hardacre, et al., React. Chem. Eng. 4 (2019) 1790–1802. doi: 10.1039/c9re00167k
85. [85]
  R. Tiwari, A. Rahman, N.S. Bhat, et al., ChemistrySelect 4 (2019) 9119–9123. doi: 10.1002/slct.201902208
86. [86]
  J. Wang, H. Yu, Z. Wei, et al., Research 2020 (2020) 3875920.
87. [87]
  O.M. Portilla-Zuñiga, J.J. Martínez, M. Casella, et al., Mol. Catal. 494 (2020).
88. [88]
  X. Jing, Z. Li, W. Geng, et al., J. Mater. Chem. A 9 (2021) 8480–8488. doi: 10.1039/d0ta11188k
89. [89]
  F. Rajabi, C. Wilhelm, W.R. Thiel, Green Chem. 22 (2020) 4438–4444. doi: 10.1039/d0gc01354d
90. [90]
  Z. Sun, X. Duan, P. Gnanasekarc, et al., Biomass Convers. Bior. 12 (2022) 2313–2331. doi: 10.1007/s13399-020-00802-1
91. [91]
  J. Schnee, A. Eggermont, E.M. Gaigneaux, ACS Catal. 7 (2017) 4011–4017. doi: 10.1021/acscatal.7b00808
92. [92]
  K. Yamamoto, M. Kuriyama, O. Onomura, Acc. Chem. Res. 53 (2020) 105–120. doi: 10.1021/acs.accounts.9b00513
93. [93]
  Y.C. Zhang, F. Jiang, F. Shi, Acc. Chem. Res. 53 (2020) 425–446. doi: 10.1021/acs.accounts.9b00549
94. [94]
  M.Z. Wang, H. Xu, T.W. Liu, et al., Eur. J. Med. Chem. 46 (2011) 1463–1472. doi: 10.1016/j.ejmech.2011.01.031
95. [95]
  M. Soltani, I. Mohammadpoor-Baltork, A.R. Khosropour, et al., C. R. Chim. 19 (2016) 381–389. doi: 10.1016/j.crci.2015.11.006
96. [96]
  S. Basu, T. Ghosh, S. Maity, et al., ChemistrySelect 4 (2019) 5763–5767. doi: 10.1002/slct.201901011
97. [97]
  H. Kamauchi, Y. Shiraishi, A. Kojima, et al., J. Nat. Prod. 81 (2018) 1290–1294. doi: 10.1021/acs.jnatprod.7b00976
98. [98]
  R. Karmakar, P. Pahari, D. Mal, Chem. Rev. 114 (2014) 6213–6284. doi: 10.1021/cr400524q
99. [99]
  X. Pang, X. Lin, J. Yang, et al., J. Nat. Prod. 81 (2018) 1860–1868. doi: 10.1021/acs.jnatprod.8b00345
100. [100]
  N. Zheng, F. Yao, X. Liang, et al., Nat. Prod. Res. 32 (2018) 755–760. doi: 10.1080/14786419.2017.1311892
101. [101]
  G.P. Yang, K. Li, X.L. Lin, et al., Chin. J. Chem. 39 (2021) 3017–3022. doi: 10.1002/cjoc.202100397
102. [102]
  Y.F. Liu, G.M. Cao, L. Chen, et al., Adv. Synth. Catal. 364 (2022) 1460–1464. doi: 10.1002/adsc.202200081
103. [103]
  A. Ansari, A. Ali, M. Asif, et al., New J. Chem. 41 (2017) 16–41. doi: 10.1039/C6NJ03181A
104. [104]
  Z. Xu, C. Gao, Q.C. Ren, et al., Eur. J. Med. Chem. 139 (2017) 429–440. doi: 10.1016/j.ejmech.2017.07.059
105. [105]
  D. Sar, R. Bag, A. Yashmeen, et al., Org. Lett. 17 (2015) 5308–5311. doi: 10.1021/acs.orglett.5b02669
106. [106]
  L. Wang, X. Yu, X. Feng, et al., J. Org. Chem. 78 (2013) 1693–1698. doi: 10.1021/jo302732v
107. [107]
  G.P. Yang, X. He, B. Yu, et al., Appl. Organomet. Chem. 32 (2018) e4532. doi: 10.1002/aoc.4532
108. [108]
  G.P. Yang, S.X. Shang, B. Yu, et al., Inorg. Chem. Front. 5 (2018) 2472–2477. doi: 10.1039/c8qi00678d
109. [109]
  M. Cheng, Y. Liu, W. Du, et al., Chin. Chem. Lett. 33 (2022) 3899–3902. doi: 10.1016/j.cclet.2021.11.059
110. [110]
  K. Li, X.L. Lin, K. Zeng, et al., Tungsten 4 (2022) 149–157. doi: 10.1007/s42864-021-00119-0
111. [111]
  G.P. Yang, Y.F. Liu, X.L. Lin, et al., Chin. Chem. Lett. 33 (2022) 354–357. doi: 10.1016/j.cclet.2021.05.008
112. [112]
  G.P. Yang, X.L. Zhang, Y.F. Liu, et al., Inorg. Chem. Front. 8 (2021) 4650–4656. doi: 10.1039/d1qi00485a
113. [113]
  M.Y. Yao, Y.F. Liu, X.X. Li, et al., Chem. Commun. 58 (2022) 5737–5740. doi: 10.1039/d2cc01051h
114. [114]
  K. Li, Y.F. Liu, X.L. Lin, et al., Inorg. Chem. 61 (2022) 6934–6942. doi: 10.1021/acs.inorgchem.2c00287
115. [115]
  G.P. Yang, X. Xie, M. Cheng, et al., Chin. Chem. Lett. 33 (2022) 1483–1487. doi: 10.1016/j.cclet.2021.08.037
116. [116]
  D. Zhang, L. Ren, A. Liu, et al., Monatsh. Chem. Chem. Mon. 153 (2022) 257–266. doi: 10.1007/s00706-022-02902-2
117. [117]
  L. Wang, K.W. Woods, Q. Li, et al., J. Med. Chem. 45 (2002) 1697–1711. doi: 10.1021/jm010523x
118. [118]
  E. Eidi, M.Z. Kassaee, Z. Nasresfahani, Appl. Organomet. Chem. 30 (2016) 561–565. doi: 10.1002/aoc.3470
119. [119]
  J. Jayram, V. Jeena, Green Chem. 19 (2017) 5841–5845. doi: 10.1039/C7GC02484C
120. [120]
  M. Shaker, A. Davoodnia, H. Vahedi, et al., J. Heterocyclic. Chem. 54 (2017) 313–317. doi: 10.1002/jhet.2585
121. [121]
  M. Masteri-Farahani, A. Ezabadi, R. Mazarei, et al., Appl. Organomet. Chem. 34 (2020) e5727.
122. [122]
  B. Maleki, H. Eshghi, A. Khojastehnezhad, et al., RSC Adv. 5 (2015) 64850–64857. doi: 10.1039/C5RA10534J
123. [123]
  M. Esmaeilpour, J. Javidi, M. Zandi, New J. Chem. 39 (2015) 3388–3398. doi: 10.1039/C5NJ00050E
124. [124]
  A. Hashemzadeh, M.M. Amini, R. Tayebee, et al., Mol. Catal. 440 (2017) 96–106. doi: 10.1016/j.mcat.2017.07.010
125. [125]
  A. Hassankhani, E. Mosaddegh, S.Y. Ebrahimipour, Arab. J. Chem. 9 (2016) S936–S939. doi: 10.1016/j.arabjc.2011.10.003
126. [126]
  R. Tayebee, M. Fattahi Abdizadeh, B. Maleki, et al., J. Mol. Liq. 241 (2017) 447–455. doi: 10.1016/j.molliq.2017.06.033
127. [127]
  X. Feng, T. Yang, X. He, et al., Appl. Organomet. Chem. 32 (2018) e4314. doi: 10.1002/aoc.4314
128. [128]
  D.M. Clode, Chem. Rev. 79 (1979) 491–513. doi: 10.1021/cr60322a002
129. [129]
  V. Kannan, K. Sreekumar, A. Gil, et al., Catal. Lett. 141 (2011) 1118–1122. doi: 10.1007/s10562-011-0572-8
130. [130]
  Y. Dai, B.D. Li, H.D. Quan, et al., Chin. Chem. Lett. 21 (2010) 678–681. doi: 10.1016/j.cclet.2010.02.004
131. [131]
  L. Fang, K. Zhang, L. Chen, et al., Chin. J. Catal. 34 (2013) 932–941. doi: 10.1016/S1872-2067(12)60591-9
132. [132]
  K.I. Shimizu, E. Hayashi, T. Hatamachi, et al., J. Catal. 231 (2005) 131–138. doi: 10.1016/j.jcat.2005.01.017
133. [133]
  M.X. Tan, L. Gu, N. Li, et al., Green Chem. 15 (2013) 1127–1132. doi: 10.1039/c3gc40297e
134. [134]
  S. Zhao, Y. Jia, Y.F. Song, Catal. Sci. Technol. 4 (2014) 2618–2625. doi: 10.1039/C4CY00021H
135. [135]
  J. Castanheiro, Catalysts 12 (2022) 81. doi: 10.3390/catal12010081
136. [136]
  L. j. Liu, Q. j. Luan, J. Lu, et al., RSC Adv. 8 (2018) 26180–26187. doi: 10.1039/C8RA04471F
137. [137]
  S. Sadjadi, S. Tarighi, N.S. Moussavi, et al., J. Mol. Struct. 1256 (2022) 132556. doi: 10.1016/j.molstruc.2022.132556
138. [138]
  A.E. Clatworthy, E. Pierson, D.T. Hung, Nat. Chem. Biol. 3 (2007) 541–548. doi: 10.1038/nchembio.2007.24
139. [139]
  S. Ravi Kanth, G. Venkat Reddy, K. Hara Kishore, et al., Eur. J. Med. Chem. 41 (2006) 1011–1016. doi: 10.1016/j.ejmech.2006.03.028
140. [140]
  J. Safari, M. Tavakoli, M.A. Ghasemzadeh, J. Organomet. Chem. 880 (2019) 75–82. doi: 10.1016/j.jorganchem.2018.10.028
141. [141]
  S.M. Vahdat, S. Khaksar, M. Akbari, et al., Arab. J. Chem. 12 (2019) 1515–1521. doi: 10.1016/j.arabjc.2014.10.026
142. [142]
  A. Samzadeh-Kermani, Synlett 27 (2016) 461–464.
143. [143]
  S. Jannati, A.A. Esmaeili, Tetrahedron 74 (2018) 2967–2972. doi: 10.1016/j.tet.2018.04.092
144. [144]
  M. Rohaniyan, A. Davoodnia, S.A. Beyramabadi, et al., Appl. Organomet. Chem. 33 (2019) e4881. doi: 10.1002/aoc.4881
145. [145]
  E. Abbaspour-Gilandeh, M. Aghaei-Hashjin, A. Yahyazadeh, et al., RSC Adv. 6 (2016) 55444–55462. doi: 10.1039/C6RA09818E
146. [146]
  Z. Zhao, K. Kang, J. Yue, et al., Eur. J. Med. Chem. 210 (2021) 113073. doi: 10.1016/j.ejmech.2020.113073
147. [147]
  G. Yang, K. Li, K. Zeng, et al., RSC Adv. 11 (2021) 10610–10614. doi: 10.1039/d1ra01004b
148. [148]
  M. Ashok, B.S. Holla, N.S. Kumari, Eur. J. Med. Chem. 42 (2007) 380–385. doi: 10.1016/j.ejmech.2006.09.003
149. [149]
  R. Medyouni, W. Elgabsi, O. Naouali, et al., Spectrochim. Acta A: Mol. Biomol. Spectrosc. 167 (2016) 165–174. doi: 10.1016/j.saa.2016.04.045
150. [150]
  L.G. do Nascimento, I.M. Dias, G.B. Meireles de Souza, et al., J. Org. Chem. 85 (2020) 11170–11180. doi: 10.1021/acs.joc.0c01167
151. [151]
  M.M. Heravi, V. Zadsirjan, Curr. Org. Chem. 24 (2020) 1331–1366. doi: 10.2174/1385272824999200616111228
152. [152]
  H. Nagarajaiah, A. Mukhopadhyay, J.N. Moorthy, Tetrahedron Lett. 57 (2016) 5135–5149. doi: 10.1016/j.tetlet.2016.09.047
153. [153]
  A. Moussa, A. Rahmati, ChemistryOpen 10 (2021) 764–774. doi: 10.1002/open.202100063
154. [154]
  L. Saher, M. Makhloufi-Chebli, L. Dermeche, et al., Tetrahedron Lett. 57 (2016) 1492–1496. doi: 10.1016/j.tetlet.2016.02.077
155. [155]
  L.D. Fader, R. Bethell, P. Bonneau, et al., Bioorg. Med. Chem. Lett. 21 (2011) 398–404. doi: 10.1016/j.bmcl.2010.10.131
156. [156]
  J. Zhou, T. Yu, K. Li, et al., Inorg. Chem. 61 (2022) 3050–3057. doi: 10.1021/acs.inorgchem.1c03160
157. [157]
  M.D. Morales, A. Infantes-Molina, J.M. Lázaro-Martínez, et al., Mol. Catal. 485 (2020) 110842. doi: 10.1016/j.mcat.2020.110842
158. [158]
  Y.P. Sarnikar, D.O. Biradar, Y.D. Mane, et al., J. Heterocyclic. Chem. 56 (2019) 1111–1116. doi: 10.1002/jhet.3500
159. [159]
  R. Mohebat, P. Dehgan, A. Yazdani-Elah-Abadi, J. Chin. Chem. Soc. 65 (2018) 1259–1265. doi: 10.1002/jccs.201800071
160. [160]
  M.T. Lv, Y.F. Liu, K. Li, et al., Tetrahedron Lett. 65 (2021) 152757. doi: 10.1016/j.tetlet.2020.152757
161. [161]
  R.J.H. Gregory, Chem. Rev. 99 (1999) 3649–3682. doi: 10.1021/cr9902906
162. [162]
  F. Fei, H. An, C. Meng, et al., RSC Adv. 5 (2015) 18796–18805. doi: 10.1039/C4RA16237D
163. [163]
  J. Li, S. Shang, Z. Lin, et al., Front. Chem. 8 (2020) 598961–598971. doi: 10.3389/fchem.2020.598961
164. [164]
  S. Li, Y. Zhou, Q. Peng, et al., Inorg. Chem. 57 (2018) 6624–6631. doi: 10.1021/acs.inorgchem.8b00763
165. [165]
  W. Xiao, S. Li, Y. Zhao, et al., Dalton Trans. 50 (2021) 8690–8695. doi: 10.1039/d1dt00924a
166. [166]
  D.L. Collins-Wildman, M. Kim, K.P. Sullivan, et al., ACS Catal. 8 (2018) 7068–7076. doi: 10.1021/acscatal.8b00394
167. [167]
  M. Nakamura, M.S. Islam, M.A. Rahman, et al., RSC Adv. 11 (2021) 34558–34563. doi: 10.1039/d1ra04426e
168. [168]
  Y. Liu, W. Liu, L. Wang, et al., Ind. Eng. Chem. Res. 57 (2018) 5207–5214. doi: 10.1021/acs.iecr.8b00240
169. [169]
  D. Zhang, W. Zhang, Z. Lin, et al., Inorg. Chem. 59 (2020) 9756–9764. doi: 10.1021/acs.inorgchem.0c00976
1. [1]
  Dan Feng LI , Yi Hang GUO , Chang Wen HU , Li MAO , En Bo WANG . Kinetics of Photocatalytic Degradation of Formic Acid over Silica Composite Films Based on Polyoxometalates. Chinese Chemical Letters, 2002, 13(6): 575-578.
2. [2]
  Kejie Qin , Dejin Zang , Yongge Wei . Polyoxometalates based compounds for green synthesis of aldehydes and ketones. Chinese Chemical Letters, 2023, 34(8): 107999-1-107999-12. doi: 10.1016/j.cclet.2022.107999
3. [3]
  Guoping Yang , Yufeng Liu , Ke Li , Wei Liu , Bing Yu , Changwen Hu . H₃PMo₁₂O₄₀-catalyzed coupling of diarylmethanols with epoxides/diols/aldehydes toward polyaryl-substituted aldehydes. Chinese Chemical Letters, 2020, 31(12): 3233-3236. doi: 10.1016/j.cclet.2020.07.018
4. [4]
  Jing Yang , Juan Zhang , Tian Tian Chen , De Mei Sun , Ji Li , Xue Fen Wu . Sulfamic acid as a cost-effective and recyclable solid acid catalyst for Friedel-Crafts alkylation of indole with α,β-unsaturated carbonyl compound and benzyl alcohol. Chinese Chemical Letters, 2011, 22(12): 1391-1394. doi: 10.1016/j.cclet.2011.06.006
5. [5]
  Jing Ping WANG , Xiao Di DU , Xian Ying DUAN , Jing Yang NIU . Synthesis and Crystal Structure of an Organic-inorganic Complex [Hg(DMSO)₂(H₂O)]₂ [GeW₁₂O₄₀]·DMSO·H₂O. Chinese Chemical Letters, 2006, 17(8): 1081-1084.
6. [6]
  Zhen Gang SUN , Jing Fu LIU , Xiao Hong WANG , Shu Mei YUE , Jian Xin LI . Synthesis, Structure of Organophosphonyl Polyoxotungstates of Formula [C₆H₁₁P(O)]₂ Xⁿ⁺W₁₁O₃₉^(8-n)-(Xⁿ⁺=P⁵⁺, Si⁴⁺, B³⁺, Ga³⁺). Chinese Chemical Letters, 1999, 10(8): 705-706.
7. [7]
  Zhen Gang SUN , Jian Xin LI , Qun LIU , Jing Fu LIU . Synthesis, structure and spectroscopic properties oforganophosphoryl polyoxotungstates of Formula α-[R₂PW₉O₃₄]₅-(R=C₆H₅P(S), C₆H₁₁P_(O)). Chinese Chemical Letters, 1999, 10(11): 971-972.
8. [8]
  Zhong Sun , Hai-Zhou Bie , Mei-Jie Wei , Jing-Jing Wang , Xu-Guang Mi , Xiao-Hong Wang , Yin Wu . Fabrication of inorganic-organic hybrid based on polyoxometalate SiW₁₀Fe₂ and folate as peroxidases for colorimetric immunoassay of cancer cells. Chinese Chemical Letters, 2013, 24(01): 76-78.
9. [9]
  Chun-Hong Li , Qiang Wang , Ying-Nan Chi , Xin-Fang Wang , Chang-Wen Hu . Supramolecular assembly of Keggin polyoxomolybdate and 2, 2'-bipyridine generated in situ from a decarboxylation coupling reaction. Chinese Chemical Letters, 2013, 24(07): 578-580.
10. [10]
  Fa Wang Chen , Tao Dong , Xiao Fang Li , Tie Gang Xu , Chang Wen Hu . Tetrabutylammonium salts of tritransition-metal-substituted A-α-tungstogermanate:Halogen-free and single-component catalysts for the coupling reaction of carbon dioxide and epichlorohydrin. Chinese Chemical Letters, 2011, 22(7): 871-874. doi: 10.1016/j.cclet.2011.01.004
11. [11]
  Masoumeh Tabatabaee , Maria Roozbeh , Mandana Roozbeh . Catalytic effect of lucunary heteropolyanion containing molybdenum and tungsten atoms on decolorization of direct blue 71. Chinese Chemical Letters, 2011, 22(12): 1501-1504. doi: 10.1016/j.cclet.2011.07.016
12. [12]
  Guoping Yang , Yufeng Liu , Xiaoling Lin , Bangming Ming , Ke Li , Changwen Hu . Self-assembly of a new 3D platelike ternary-oxo-cluster: An efficient catalyst for the synthesis of pyrazoles. Chinese Chemical Letters, 2022, 33(1): 354-357. doi: 10.1016/j.cclet.2021.05.008
13. [13]
  Xiaofeng Fan , Wei Pang , Hao Feng , Ruiyi Zhang , Wentao Zhu , Qiushi Wang , Jun Miao , Yiwen Li , Yanjun Liu , Xiaoqian Xu . Light-guided tumor diagnosis and therapeutics: From nanoclusters to polyoxometalates. Chinese Chemical Letters, 2022, 33(6): 2783-2798. doi: 10.1016/j.cclet.2021.12.057
14. [14]
  Shurong Li , Zhenzhang Weng , Linpeng Jiang , Rongjia Wei , Haifeng Su , Lasheng Long , Lansun Zheng , Xiangjian Kong . A series of heterometallic 3d-4f polyoxometalates as single-molecule magnets. Chinese Chemical Letters, 2023, 34(3): 107251-1-107251-4. doi: 10.1016/j.cclet.2022.02.056
15. [15]
  Qianxia Gu , Xiao-Li Zhao , Min Meng , Zhiyu Shao , Qi Zheng , Weimin Xuan . Crystalline porous ionic salts assembled from polyoxometalates and cationic capsule for the selective photocatalytic aerobic oxidation of aromatic alcohols to aldehydes. Chinese Chemical Letters, 2023, 34(4): 107444-1-107444-4. doi: 10.1016/j.cclet.2022.04.042
16. [16]
  Yubin Ma , Fan Gao , Wanru Xiao , Na Li , Shujun Li , Bing Yu , Xuenian Chen . Two transition-metal-modified Nb/W mixed-addendum polyoxometalates for visible-light-mediated aerobic benzylic C–H oxidations. Chinese Chemical Letters, 2022, 33(9): 4395-4399. doi: 10.1016/j.cclet.2021.12.023
17. [17]
  Feng Enqi , Hou Zhongwei , Xu Haichao . Electrochemical Synthesis of Tetrasubstituted Hydrazines by Dehydrogenative N-N Bond Formation. Chinese Journal of Organic Chemistry, 2019, 39(5): 1424-1428. doi: 10.6023/cjoc201812007
18. [18]
  Hou Jiao , Zhang Xinting , Yu Wenquan , Chang Junbiao . I₂-Mediated Oxidative C-O Bond Formation for the Synthesis of Isoxazoles. Chinese Journal of Organic Chemistry, 2018, 38(12): 3236-3241. doi: 10.6023/cjoc201806026
19. [19]
  Daoshan Yang , Qiuli Yan , Enjie Zhu , Jian Lv , Wei-Min He . Carbon–sulfur bond formation via photochemical strategies: An efficient method for the synthesis of sulfur-containing compounds. Chinese Chemical Letters, 2022, 33(4): 1798-1816. doi: 10.1016/j.cclet.2021.09.068
20. [20]
  Hong-Qiang Liu , Jun Liu , Yang-Hui Zhang , Chang-Dong Shao , Jing-Xun Yu . Copper-catalyzed amide bond formation from formamides and carboxylic acids. Chinese Chemical Letters, 2015, 26(1): 11-14. doi: 10.1016/j.cclet.2014.09.007

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(128)
HTML views(26)

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