Citation: Hua Liu, Jian Zhao, Qi Li, Xiang-Yu Zhang, Zhi-Wei Zheng, Kun Huang, Da-Bin Qin, Bin Zhao. Indium-captured zirconium-porphyrin frameworks displaying rare multi-selectivity for catalytic transfer hydrogenation of aldehydes and ketones[J]. Chinese Chemical Letters, ;2025, 36(6): 110593. doi: 10.1016/j.cclet.2024.110593 shu

Indium-captured zirconium-porphyrin frameworks displaying rare multi-selectivity for catalytic transfer hydrogenation of aldehydes and ketones

Hua Liu ^{a, 1} ,
Jian Zhao ^{b, 1} ,
Qi Li ^b ,
Xiang-Yu Zhang ^{a, b, *,} ,
Zhi-Wei Zheng ^a ,
Kun Huang ^a ,
Da-Bin Qin ^{a, *,} ,
Bin Zhao ^{a, b, *,}

a.
Key Laboratory of Chemical Synthesis and Pollution Control of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, China
b.
Frontiers Science Center for New Organic Matter, Key Laboratory of Advanced Energy Materials Chemistry (MOE), College of Chemistry, Nankai University, Tianjin 300071, China

xyzhang@cwnu.edu.cn

qdbkyl@cwnu.edu.cn

zhaobin@nankai.edu.cn

Received Date: 29 July 2024
Revised Date: 23 October 2024
Accepted Date: 29 October 2024
Available Online: 30 October 2024

Figures(8)

Selective catalytic transfer hydrogenation (CTH) of carbonyl compounds to obtain specific alcohols holds significant importance across various fields. Achieving multiple selectivity in CTH is particularly crucial, but full of great challenge. Herein, a cationic In-captured Zr-porphyrin framework (1) with nanosized pores/cages was successfully constructed and showed high structure stability. Catalytic investigations revealed that 1 displayed highly multi-selective CTH of aldehydes and ketones containing both chemo- and size selectivity for the first time. The CTH of aldehydes and ketones exhibited remarkable reductive selectivity of 99% towards CO bonds into CHOH in the presence of -NO₂, -CN and CC groups. Through tuning the reaction conditions, 1 also exhibited highly selective reduction of 97% for -CHO groups in the simultaneous presence of -CHO and -COCH₃ groups in intra- and intermolecular settings. Remarkably, reductive selectivity towards -CHO group remained prominent among five concurrent unsaturated groups mentioned above. Additionally, the definite pore size of 1 facilitated volume control of substrates, enabling size selectivity. 1 as a heterogeneous catalyst was further confirmed by leaching tests, and maintained high activity even after being used for at least six cycles. Mechanistic studies have revealed that Zr₆O₈ clusters served as the catalytic centers and the observed chemoselectivity mainly results from the synergistic effect of distinct metal sites within 1. The heightened selectivity towards -CHO over -COCH₃ can be attributed to the easier realization of transfer hydrogenation processes for -CHO compared to -COCH₃.
- Metal-organic framework,
- Heterogeneous catalysis,
- Transfer hydrogenation,
- Multiple selectivity,
- Synergistic effect
1. [1]
  W. Zuo, A.J. Lough, Y.F. Li, et al., Science 342 (2013) 1080–1083. doi: 10.1126/science.1244466
2. [2]
  M. Zhao, K. Yuan, Y. Wang, et al., Nature 539 (2016) 76–80. doi: 10.1038/nature19763
3. [3]
  L. Zhang, M. Zhou, A. Wang, et al., Chem. Rev. 120 (2020) 683–733. doi: 10.1021/acs.chemrev.9b00230
4. [4]
  Y. Wang, Z. Huang, X. Leng, et al., J. Am. Chem. Soc. 140 (2018) 4417–4429. doi: 10.1021/jacs.8b01038
5. [5]
  L. Wang, J. Lin, Q. Sun, et al., ACS Catal. 11 (2021) 8033–8041. doi: 10.1021/acscatal.1c00616
6. [6]
  F. Wang, T. Yang, T. Wu, et al., J. Am. Chem. Soc. 143 (2021) 2477–2483. doi: 10.1021/jacs.0c13273
7. [7]
  X. Li, W. Hao, N. Yi, et al., CCS Chem. 5 (2023) 2277–2289. doi: 10.31635/ccschem.023.202303007
8. [8]
  D. Wang, D. Astruc, Chem. Rev. 115 (2015) 6621–6686. doi: 10.1021/acs.chemrev.5b00203
9. [9]
  Y.Y. Li, S.L. Yu, W.Y. Shen, et al., Acc. Chem. Res. 48 (2015) 2587–2598. doi: 10.1021/acs.accounts.5b00043
10. [10]
  Z. An, J. Li, Green Chem. 24 (2022) 1780–1808. doi: 10.1039/d1gc04440k
11. [11]
  A.H. Valekar, M. Lee, J.W. Yoon, et al., ACS Catal. 10 (2020) 3720–3732. doi: 10.1021/acscatal.9b05085
12. [12]
  J. Wei, L. Zhao, C. He, et al., J. Am. Chem. Soc. 141 (2019) 12707–12716. doi: 10.1021/jacs.9b05351
13. [13]
  R.A. Farrar-Tobar, A. Dell'Acqua, S. Tin, et al., Green Chem. 22 (2020) 3323–3357. doi: 10.1039/d0gc00855a
14. [14]
  S.M. King, X. Ma, S.B. Herzon, J. Am. Chem. Soc. 136 (2014) 6884–6887. doi: 10.1021/ja502885c
15. [15]
  C.K. Hill, J.F. Hartwig, Nat. Chem. 9 (2017) 1213–1221. doi: 10.1038/nchem.2835
16. [16]
  Y. Ren, Y. Yang, M. Wei, ACS Catal. 13 (2023) 8902–8924. doi: 10.1021/acscatal.3c01442
17. [17]
  W. Gong, X. Chen, W. Zhang, et al., J. Am. Chem. Soc. 144 (2022) 3117–3126. doi: 10.1021/jacs.1c12117
18. [18]
  X.R. Tian, Z.Y. Jiang, S.L. Hou, et al., Angew. Chem. Int. Ed. 62 (2023) e202301764. doi: 10.1002/anie.202301764
19. [19]
  G.D. Wang, Y.Z. Li, W.J. Shi, et al., Angew. Chem. Int. Ed. 62 (2023) e202311654. doi: 10.1002/anie.202311654
20. [20]
  L. Sun, X. He, Y. Yuan, et al., Chem. Eng. J. 397 (2020) 125468. doi: 10.1016/j.cej.2020.125468
21. [21]
  K. Sun, Y. Qian, H.L. Jiang, Angew. Chem. Int. Ed. 62 (2023) e202217565. doi: 10.1002/anie.202217565
22. [22]
  C.P. Wang, Y.X. Lin, L. Cui, et al., Small 19 (2023) 2207342. doi: 10.1002/smll.202207342
23. [23]
  E.X. Chen, M. Qiu, Y.F. Zhang, et al., Angew. Chem. Int. Ed. 61 (2022) e202111622. doi: 10.1002/anie.202111622
24. [24]
  X. Chen, C. Peng, W. Dan, et al., Nat. Commun. 13 (2022) 4592. doi: 10.1038/s41467-022-32367-0
25. [25]
  Q. Wu, A. Li, R. He, et al., Chin. Chem. Lett. 35 (2024) 108639. doi: 10.1016/j.cclet.2023.108639
26. [26]
  X. Kou, Y. Lin, Y. Shen, et al., CCS Chem. 6 (2024) 1821–1835. doi: 10.31635/ccschem.023.202303541
27. [27]
  R.J. Wei, H.G. Zhou, Z.Y. Zhang, et al., CCS Chem. 3 (2021) 2045–2053. doi: 10.31635/ccschem.020.202000401
28. [28]
  M. Zhao, S. Huang, Q. Fu, et al., Angew. Chem. Int. Ed. 59 (2020) 20031–20036. doi: 10.1002/anie.202007122
29. [29]
  K. Sheng, L.M. Fan, X.F. Tian, et al., Sci. Chin. Chem. 63 (2020) 182–186. doi: 10.1007/s11426-019-9621-x
30. [30]
  L. Yang, P. Cai, L. Zhang, et al., J. Am. Chem. Soc. 143 (2021) 12129–12137. doi: 10.1021/jacs.1c03960
31. [31]
  X.C. Lin, Y.M. Wang, X. Chen, et al., Angew. Chem. Int. Ed. 62 (2023) e202306497. doi: 10.1002/anie.202306497
32. [32]
  F. Guo, R.X. Li, S. Yang, et al., Angew. Chem. Int. Ed. 62 (2023) e202216232. doi: 10.1002/anie.202216232
33. [33]
  X.S. Jiang, F.Y. Ren, Y. Shi, et al., CCS Chem. 6 (2024) 2333–2345. doi: 10.31635/ccschem.024.202303476
34. [34]
  X.S. Li, J. Zhao, S.L. Hou, et al., CCS Chem. 6 (2024) 2982–2995. doi: 10.31635/ccschem.024.202404341
35. [35]
  X.S. Li, J. Zhao, L. Luo, et al., Chin. Chem. Lett. 35 (2024) 109407. doi: 10.1016/j.cclet.2023.109407
36. [36]
  Y.S. Wei, M. Zhang, R. Zou, et al., Chem. Rev. 120 (2020) 12089–12174. doi: 10.1021/acs.chemrev.9b00757
37. [37]
  T. He, X.J. Kong, J.R. Li, Acc. Chem. Res. 54 (2021) 3083–3094. doi: 10.1021/acs.accounts.1c00280
38. [38]
  Y. Song, X. Feng, J.S. Chen, et al., J. Am. Chem. Soc. 142 (2020) 4872–4882. doi: 10.1021/jacs.0c00073
39. [39]
  Q.J. Wu, J. Liang, Y.B. Huang, et al., Acc. Chem. Res. 55 (2022) 2978–2997. doi: 10.1021/acs.accounts.2c00326
40. [40]
  Z. Ji, H. Wang, S. Canossa, et al., Adv. Funct. Mater. 30 (2020) 2000238. doi: 10.1002/adfm.202000238
41. [41]
  C.X. Chen, Z.W. Wei, T. Pham, et al., Angew. Chem. Int. Ed. 60 (2021) 9680–9685. doi: 10.1002/anie.202100114
42. [42]
  G. Ji, L. Zhao, J. Wei, et al., Angew. Chem. Int. Ed. 61 (2022) e202114490. doi: 10.1002/anie.202114490
43. [43]
  N. Li, G.Q. Lai, L.H. Chung, et al., CCS Chem. 6 (2023) 1211–1221.
44. [44]
  S. Fu, S. Yao, S. Guo, et al., J. Am. Chem. Soc. 143 (2021) 20792–20801. doi: 10.1021/jacs.1c08908
45. [45]
  P. Vasanthakumar, D.S. Raja, D. Sindhuja, et al., Mol. Catal. 516 (2021) 112004. doi: 10.1016/j.mcat.2021.112004
46. [46]
  D. Feng, W.C. Chung, Z. Wei, et al., J. Am. Chem. Soc. 135 (2013) 17105–17110. doi: 10.1021/ja408084j
47. [47]
  G. Zhai, Y. Liu, L. Lei, et al., ACS Catal. 11 (2021) 1988–1994. doi: 10.1021/acscatal.0c05145
48. [48]
  P. Jin, L. Wang, X. Ma, et al., Appl. Catal. B: Environ. 284 (2021) 119762. doi: 10.1016/j.apcatb.2020.119762
49. [49]
  M.W. Geis, T.H. Fedynyshyn, M.E. Plaut, et al., Diam. Relat. Mater. 84 (2018) 86–94. doi: 10.1016/j.diamond.2018.03.002
50. [50]
  H. Liu, H.J. Li, Z.W. Zheng, et al., Cryst. Growth Des. 23 (2023) 7316–7324. doi: 10.1021/acs.cgd.3c00716
51. [51]
  H. Liu, Z.W. Zheng, X.Y. Zhang, et al., Inorg. Chem. 63 (2024) 11554–11565. doi: 10.1021/acs.inorgchem.4c00659
52. [52]
  Q. Wang, Z. Wei, J. Li, et al., ACS Appl. Mater. Interfaces 14 (2022) 27775–27790. doi: 10.1021/acsami.2c01378
53. [53]
  F.A. Westerhaus, R.V. Jagadeesh, G. Wienhöfer, et al., Nat. Chem. 5 (2013) 537–543. doi: 10.1038/nchem.1645
54. [54]
  J. Zhang, L. Wang, Y. Shao, et al., Angew. Chem. Int. Ed. 56 (2017) 9747–9751. doi: 10.1002/anie.201703938
55. [55]
  R.B. Nasir Baig, R.S. Varma, ACS Sustain. Chem. Eng. 1 (2013) 805–809. doi: 10.1021/sc400032k
56. [56]
  W. Walczak, M. Zakrzewski, G. Cichowicz, et al., Org. Biomol. Chem. 18 (2020) 694–699. doi: 10.1039/c9ob02234a
57. [57]
  Z.W. Xi, L. Yang, D.Y. Wang, et al., J. Org. Chem. 86 (2021) 2474–2488. doi: 10.1021/acs.joc.0c02627
58. [58]
  Y. Li, Y.N. Li, J.W. Zheng, et al., Chem. Eur. J. 27 (2021) 1080–1087. doi: 10.1002/chem.202003857
1. [1]
  Ming Huang , Xiuju Cai , Yan Liu , Zhuofeng Ke . Base-controlled NHC-Ru-catalyzed transfer hydrogenation and α-methylation/transfer hydrogenation of ketones using methanol. Chinese Chemical Letters, 2024, 35(7): 109323-. doi: 10.1016/j.cclet.2023.109323
2. [2]
  Ruiying Liu , Li Zhao , Baishan Liu , Jiayuan Yu , Yujie Wang , Wanqiang Yu , Di Xin , Chaoqiong Fang , Xuchuan Jiang , Riming Hu , Hong Liu , Weijia Zhou . Modulating pollutant adsorption and peroxymonosulfate activation sites on Co3O4@N,O doped-carbon shell for boosting catalytic degradation activity. Chinese Journal of Structural Chemistry, 2024, 43(8): 100332-100332. doi: 10.1016/j.cjsc.2024.100332
3. [3]
  Linping Li , Junhui Su , Yanping Qiu , Yangqin Gao , Ning Li , Lei Ge . Design and fabrication of ternary Au/Co3O4/ZnCdS spherical composite photocatalyst for facilitating efficient photocatalytic hydrogen production. Chinese Journal of Structural Chemistry, 2024, 43(12): 100472-100472. doi: 10.1016/j.cjsc.2024.100472
4. [4]
  Zimo Peng , Quan Zhang , Gaocan Qi , Hao Zhang , Qian Liu , Guangzhi Hu , Jun Luo , Xijun Liu . Nanostructured Pt@RuOx catalyst for boosting overall acidic seawater splitting. Chinese Journal of Structural Chemistry, 2024, 43(1): 100191-100191. doi: 10.1016/j.cjsc.2023.100191
5. [5]
  Xiangshuai Li , Jian Zhao , Li Luo , Zhuohao Jiao , Ying Shi , Shengli Hou , Bin Zhao . Visual and portable detection of metronidazole realized by metal-organic framework flexible sensor and smartphone scanning. Chinese Chemical Letters, 2024, 35(10): 109407-. doi: 10.1016/j.cclet.2023.109407
6. [6]
  Xu Huang , Kai-Yin Wu , Chao Su , Lei Yang , Bei-Bei Xiao . Metal-organic framework Cu-BTC for overall water splitting: A density functional theory study. Chinese Chemical Letters, 2025, 36(4): 109720-. doi: 10.1016/j.cclet.2024.109720
7. [7]
  Shimei Wu , Yining Li , Lantao Chen , Yufei Zhang , Lingxing Zeng , Haosen Fan . Hexapod cobalt phosphosulfide nanorods encapsulating into multiple hetero-atom doped carbon frameworks for advanced sodium/potassium ion battery anodes. Chinese Chemical Letters, 2025, 36(4): 109796-. doi: 10.1016/j.cclet.2024.109796
8. [8]
  Yuxin Wang , Zhengxuan Song , Yutao Liu , Yang Chen , Jinping Li , Libo Li , Jia Yao . Methyl functionalization of trimesic acid in copper-based metal-organic framework for ammonia colorimetric sensing at high relative humidity. Chinese Chemical Letters, 2024, 35(6): 108779-. doi: 10.1016/j.cclet.2023.108779
9. [9]
  Ning Zhang , Mengjie Qin , Jiawen Zhu , Xuejing Lou , Xiao Tian , Wende Ma , Youmei Wang , Minghua Lu , Zongwei Cai . Thickness-controllable synthesis of metal-organic framework based hollow nanoflowers with magnetic core via liquid phase epitaxy for phosphopeptides enrichment. Chinese Chemical Letters, 2025, 36(4): 110177-. doi: 10.1016/j.cclet.2024.110177
10. [10]
  Shuai Li , Liuting Zhang , Fuying Wu , Yiqun Jiang , Xuebin Yu . Efficient catalysis of FeNiCu-based multi-site alloys on magnesium-hydride for solid-state hydrogen storage. Chinese Chemical Letters, 2025, 36(1): 109566-. doi: 10.1016/j.cclet.2024.109566
11. [11]
  Rui Liu , Yue Yu , Lu Deng , Maoxia Xu , Haorong Ren , Wenjie Luo , Xudong Cai , Zhenyu Li , Jingyu Chen , Hua Yu . The synergistic effect of A-site cation engineering and phase regulation enables efficient and stable Ruddlesden-Popper perovskite solar cells. Chinese Chemical Letters, 2024, 35(12): 109545-. doi: 10.1016/j.cclet.2024.109545
12. [12]
  Xiuzheng Deng , Yi Ke , Jiawen Ding , Yingtang Zhou , Hui Huang , Qian Liang , Zhenhui Kang . Construction of ZnO@CDs@Co₃O₄ sandwich heterostructure with multi-interfacial electron-transfer toward enhanced photocatalytic CO₂ reduction. Chinese Chemical Letters, 2024, 35(4): 109064-. doi: 10.1016/j.cclet.2023.109064
13. [13]
  Heng Yang , Zhijie Zhou , Conghui Tang , Feng Chen . Recent advances in heterogeneous hydrosilylation of unsaturated carbon-carbon bonds. Chinese Chemical Letters, 2024, 35(6): 109257-. doi: 10.1016/j.cclet.2023.109257
14. [14]
  Shuai Tang , Zian Wang , Mengyi Zhu , Xinyun Zhao , Xiaoyun Hu , Hua Zhang . Synthesis of organoboron compounds via heterogeneous C–H and C–X borylation. Chinese Chemical Letters, 2025, 36(5): 110503-. doi: 10.1016/j.cclet.2024.110503
15. [15]
  Wen-Jing Li , Jun-Bo Wang , Yu-Heng Liu , Mo Zhang , Zhan-Hui Zhang . Molybdenum-doped carbon nitride as an efficient heterogeneous catalyst for direct amination of nitroarenes with arylboronic acids. Chinese Chemical Letters, 2025, 36(3): 110001-. doi: 10.1016/j.cclet.2024.110001
16. [16]
  Xian-Fa Jiang , Chongyun Shao , Zhongwen Ouyang , Zhao-Bo Hu , Zhenxing Wang , You Song . Generating electron spin qubit in metal-organic frameworks via spontaneous hydrolysis. Chinese Chemical Letters, 2024, 35(7): 109011-. doi: 10.1016/j.cclet.2023.109011
17. [17]
  Xuying Yu , Jiarong Mi , Yulan Han , Cai Sun , Mingsheng Wang , Guocong Guo . A stable radiochromic semiconductive viologen-based metal–organic framework for dual-mode direct X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109233-. doi: 10.1016/j.cclet.2023.109233
18. [18]
  Fengrui Yang , Debing Wang , Xinying Zhang , Jie Zhang , Zhichao Wu , Qiaoying Wang . Synergistic effects of peroxydisulfate on UV/O₃ process for tetracycline degradation: Mechanism and pathways. Chinese Chemical Letters, 2024, 35(10): 109599-. doi: 10.1016/j.cclet.2024.109599
19. [19]
  Ke Gong , Jinghan Liao , Jiangtao Lin , Quan Wang , Zhihua Wu , Liting Wang , Jiali Zhang , Yi Dong , Yourong Duan , Jianhua Chen . Mitochondria-targeted nanoparticles overcome chemoresistance via downregulating BACH1/CD47 axis in ovarian carcinoma. Chinese Chemical Letters, 2024, 35(5): 108888-. doi: 10.1016/j.cclet.2023.108888
20. [20]
  Baokang Geng , Xiang Chu , Li Liu , Lingling Zhang , Shuaishuai Zhang , Xiao Wang , Shuyan Song , Hongjie Zhang . High-efficiency PdNi single-atom alloy catalyst toward cross-coupling reaction. Chinese Chemical Letters, 2024, 35(7): 108924-. doi: 10.1016/j.cclet.2023.108924

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(161)
HTML views(3)

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