Citation: Zhu Dong-Xing, Xu Ming-Hua. Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Aldehydes and Ketones[J]. Chinese Journal of Organic Chemistry, ;2020, 40(2): 255-275. doi: 10.6023/cjoc201910009 shu

Transition Metal-Catalyzed Asymmetric Addition of Organoboron Reagents to Aldehydes and Ketones

Zhu Dong-Xing ^a ,
Xu Ming-Hua ^a,b,,

a.
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203
b.
Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong 518055

Corresponding author: Xu Ming-Hua, xumh@sustech.edu.cn
Received Date: 10 October 2019
Revised Date: 27 October 2019
Available Online: 7 February 2019
Fund Project: the National Natural Science Foundation of China 21971103the National Natural Science Foundation of China 81521005Project supported by the National Natural Science Foundation of China (Nos. 21672229, 81521005, 21971103) and the National Science & Technology Major Project of China (No. 2018ZX09711002-006)the National Natural Science Foundation of China 21672229the National Science & Technology Major Project of China 2018ZX09711002-006

Figures(13)

Chiral aryl alcohols are prevalent in a broad range of biologically active compounds, pharmaceutical agents and natural products. They also constitute a broad class of optically active building blocks for the synthesis of important chiral compounds. In recent years, organoboron reagents are widely used in organic synthesis as they possess advantages of ready availability, low toxicity, good air and moisture stability as well as high functional group compatibility. Since the first report of rhodium-catalyzed asymmetric addition of aryl boronic acids to aryl aldehydes in 1998 by Miyaura, the use of organoboron reagents in asymmetric addition to various carbonyl compounds under various transition-metal catalyses has been intensively investigated. Over the past two decades, transition metal-catalyzed asymmetric addition of organoboron reagents to aldehydes and ketones has proved as one of the most direct and powerful methods for accessing versatile optically active alcohols. The development and progress of a wide range of chiral ligands for Rh, Ru, Pd, Ir, Cu, Ni and Co catalysis for asymmetric addition of organoboron reagents to aldehydes and ketones are summarized, and the achievements in enantioselective synthesis of chiral aryl alcohols and their applications in the synthesis of related biocative products are described. Among them, rhodium and ruthenium-catalyzed enantioselective additions have received considerable attention. In the cases of activated carbonyl compounds such as α-aryl ketoesters and α-diaryl diketones, excellent results can be attained in terms of both yield and enantioselectivity. However, it remains a daunting challenge for highly enantioselective addition to simple unactivated aldehydes and ketones owing to the difficulty in overcoming stereo differentiation. Future efforts in the community would focus on developing new effective transition-metal catalysts in addressing these issues by promoting efficient transformation and controlling excellent enantioselectivity.
- asymmetric synthesis,
- chiral alcohols,
- organoboron reagents,
- transition-metal catalysis,
- asymmetric addition
1. [1]
  (a) Dhillon, S.; Scott, L. J.; Plosker, G. L. CNS Drugs 2006, 20, 763.
  (b) Fournier, A. M.; Brown, R. A.; Farnaby, W.; Miyatake-On- dozabal, H.; Clayden, J. Org. Lett. 2010, 12, 2222.
  (c) Nathan, L. A. J. Appl. Ther. 1962, 4, 830.
2. [2]
  Bai, D. L.; Chen, K. X.; Li, S. K.; Feng, S. Adv. Med. Chem. 2011, p. 290 (in Chinese).
3. [3]
  (a) Heravi, M. M.; Zadsirjan, V.; Esfandyari, M.; Lashaki, T. B. Tetrahedron: Asymmetry 2017, 28, 987.
  (b) Zaitsev, A. B.; Adolfsson, H. Synthesis 2006, 1725.
  (c) Scott, H. K.; Aggarwal, V. K. Chem. Eur. J. 2011, 17, 13124.
  (d) Jacobsen, E. N.; Kakiuchi, F.; Konsler, R. G.; Larrow, J. F.; Tokunaga, F. Tetrahedron Lett. 1997, 38, 773.
  (e) Wang, C.; Luo, L.; Yamamoto, H. Acc. Chem. Res. 2016, 49, 193.
  (f) Sälinger, D.; Brückner, R. Chem.-Eur. J. 2009, 15, 6688.
4. [4]
  (a) Hatano, M.; Ishihara, K. Synthesis 2008, 1647.
  (b) Rong, J.; Pellegrini, T.; Harutyunyan, S. R. Chem. Eur. J. 2016, 22, 3558.
  (c) Collados, J. F.; Sol, R.; Harutyunyan, S. R.; Macià, B. ACS Catal. 2016, 6, 1952.
  (d) Pellissier, H. Tetrahedron 2015, 71, 2487.
  (e) Liu, Y. L.; Lin, X. T. Adv. Synth. Catal. 2019, 361, 876.
5. [5]
  Sakai, M.; Ueda, M.; Miyaura, N. Angew. Chem., Int. Ed. 1998, 37, 3279. doi: 10.1002/(SICI)1521-3773(19981217)37:23<3279::AID-ANIE3279>3.0.CO;2-M
6. [6]
  (a) Jiang, Z. T.; Wang, B. Q.; Shi, Z. J. Chin. J. Chem. 2018, 36, 954.
  (b) Wang, G. N.; Gan, Y.; Liu, Y. H. Chin. J. Chem. 2018, 36, 916.
7. [7]
  Focken, T.; Rudolph, J.; Bolm, C. Synthesis 2005, 429.
8. [8]
  (a) Suzuki, K.; Ishii, S.; Kondo, K.; Aoyama, T. Synlett 2006, 648.
  (b) Suzuki, K.; Kondo, K.; Aoyama, T. Synthesis 2006, 1360.
  (c) Arao, T.; Suzuki, K.; Kondo, K.; Aoyama, T. Synthesis 2006, 3809.
9. [9]
  Duan, H. F.; Xie, J. H.; Shi, W. J.; Zhang, Q.; Zhou, Q. L. Org. Lett. 2006, 8, 1479. doi: 10.1021/ol060360c
10. [10]
  Jagt, R. B. C.; Toullec, P. Y.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Org. Biomol. Chem. 2006, 4, 773. doi: 10.1039/b518311a
11. [11]
  (a) Noël, T.; Vandyck, K.; Van der Eycken, J. Tetrahedron 2007, 63, 12961.
  (b) Nishimura, T.; Kumamoto, H.; Nagaosa, M.; Hayashi, T. Chem. Commun. 2009, 45, 5713.
12. [12]
  Morikawa, S.; Michigami, K.; Amii, H. Org. Lett. 2010, 12, 2520. doi: 10.1021/ol100697a
13. [13]
  (a) Ma, Q. S.; Ma, Y. D.; Liu, X.; Duan, W. Z.; Qu, B.; Song, C. Tetrahedron: Asymmetry 2010, 21, 292.
  (b) Duan, W. Z.; Ma, Y. D.; Qu, B.; Zhao, L.; Chen, J. Q.; Song, C. Tetrahedron: Asymmetry 2012, 23, 1369.
  (c) Duan, W. Z.; Ma, Y. D.; He, F. Y.; Zhao, L.; Chen, J. Q.; Song, C. Tetrahedron: Asymmetry 2013, 24, 241.
  (d) Wang, D. X.; Ma, Y. D.; He, F. Y.; Duan, W. Z.; Zhao, L.; Song, C. Synth. Commun. 2013, 43, 810.
  (e) Chen, J. Q.; Yang, S. B.; Chen, Z.; Song, C.; Ma, Y. D. Tetrahedron: Asymmetry 2015, 26, 288.
14. [14]
  He, W. P.; Zhou, B. H.; Zhou, Y. L.; Li, X. L.; Fan, L. M.; Shou, H. W.; Li, J. Tetrahedron Lett. 2016, 57, 3152. doi: 10.1016/j.tetlet.2016.06.023
15. [15]
  Kamikawa, K.; Tseng, Y.-Y.; Jian, J.-H.; Takahashi, T.; Ogasawara, M. J. Am. Chem. Soc. 2017, 139, 1545. doi: 10.1021/jacs.6b11243
16. [16]
  (a) Yamamoto, Y.; Miyaura, N.; Kurihara, K. Angew. Chem., Int. Ed. 2009, 48, 4414.
  (b) Shirai, T.; Watanabe, M.; Kurihara, K.; Miyaura, N.; Yamamoto, Y. Molecules 2011, 16, 5020.
  (c) Yamamoto, Y.; Shirai, T.; Miyaura, N. Chem. Commun. 2012, 48, 2803.
17. [17]
  Desroches, J.; Ariane Tremblay, A.; Paquin, J.-F. Org. Biomol. Chem. 2016, 14, 8764. doi: 10.1039/C6OB01663D
18. [18]
  Li, K.; Hu, N. F.; Luo, R. S.; Yuan, W. C.; Tang, W. J. J. Org. Chem. 2013, 78, 6350. doi: 10.1021/jo400850m
19. [19]
  Lu, Z. W.; Zhang, H. Y.; Yang, Z. P.; Ding, N.; Meng, L.; Wang. J. ACS Catal. 2019, 9, 1457. doi: 10.1021/acscatal.8b04787
20. [20]
  (a) Arao, T.; Kondo, K.; Aoyama, T. Tetrahedron Lett. 2007, 48, 4115.
  (b) Yamamoto, K.; Tsurumi, K.; Sakurai, F.; Kondo, K.; Aoyama, T. Synthesis 2008, 3585.
21. [21]
  Karthikeyan, J.; Jeganmohan, M.; Cheng, C.-H. Chem.-Eur. J. 2010, 16, 8989. doi: 10.1002/chem.201001160
22. [22]
  (a) Suzuma, Y.; Hayashi, S.; Yamamoto, T.; Oe, Y.; Ohta, T.; Ito, Y. Tetrahedron: Asymmetry 2009, 20, 2751.
  (b) Loxq, P.; Debono, N.; Gülcemal, S.; Daran, J-C.; Manoury, E.; Poli, R.; Cetinkaya, B.; Labande, A. New J. Chem. 2014, 38, 338.
  (c) Zhang, R.; Xu, Q.; Zhang, X.; Zhang, T.; Shi, M. Tetrahedron: Asymmetry 2010, 21, 1928.
23. [23]
  (a) Tokunaga, T.; Hume, W. E.; Nagamine, J.; Kawamura, T.; Taiji, M.; Nagata, R. Bioorg. Med. Chem. Lett. 2005, 15, 1789.
  (b) Tokunaga, T.; Hume, W. E.; Umezome, T.; Okazaki, K.; Ueki, Y.; Kumagai, K.; Hourai, S.; Nagamine, J.; Seki, H.; Taiji, M.; Noguchi, H.; Nagata, R. J. Med. Chem. 2001, 44, 4641.
24. [24]
  Di Malta, A.; Garcia, G.; Roux, R.; Schoentjes, B.; Serradeil-le Gal, C.; Tonnerre, B.; Wagnon, J. WO 2003008407, 2003.
25. [25]
  Shintani, R.; Inoue, M.; Hayashi, T. Angew. Chem., Int. Ed. 2006, 45, 3353. doi: 10.1002/anie.200600392
26. [26]
  Toullec, P. Y.; Jagt, R. B. C.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Org. Lett. 2006, 8, 2715. doi: 10.1021/ol0608101
27. [27]
  Gui, J.; Chen, G.; Cao, P.; Liao, J. Tetrahedron: Asymmetry 2012, 23, 554. doi: 10.1016/j.tetasy.2012.04.013
28. [28]
29. [29]
  Marques, C. S.; Burke, A. J. ChemCatChem 2016, 8, 3518. doi: 10.1002/cctc.201600901
30. [30]
  Lai, H. S.; Huang, Z. Y.; Wu, Q.; Qin, Y. J. Org. Chem. 2009, 74, 283. doi: 10.1021/jo802036m
31. [31]
  Liu, Z.; Gu, P.; Shi, M.; McDowell, P.; Li, G. G. Org. Lett. 2011, 13, 2314. doi: 10.1021/ol200566s
32. [32]
  Li, Q.; Wan, P.; Wang, S.; Zhuang, Y.; Li, L.; Zhou, Y.; He, Y.; Cao, R.; Qiu, L.; Zhou, Z. Appl. Catal., A 2013, 458, 201. doi: 10.1016/j.apcata.2013.03.027
33. [33]
  (a) Yamamoto, Y.; Yohd, M.; Shirai, T.; Ito, H.; Miyaura, N. Chem. Asian J. 2012, 7, 2446.
  (b) Yohda, M.; Yamamoto, Y. Tetrahedron: Asymmetry 2015, 26, 1430.
34. [34]
  Shintani, R.; Takatsu, K.; Hayashi, T. Chem. Commun. 2010, 46, 6822. doi: 10.1039/c0cc01635g
35. [35]
  Zhuang, Y.; He, Y. W.; Zhou, Z. H.; Xia, W.; Cheng, C. Y.; Wang, M.; Chen, B.; Zhou, Z. Y.; Pang, J. Y.; Qiu, L.Y. J. Org. Chem. 2015, 80, 6968. doi: 10.1021/acs.joc.5b00595
36. [36]
  (a) Skaddan, M. B.; Kilbourn, M. R.; Snyder, S. E.; Sherman, P. S.; Desmond, T. J.; Frey, K. A. J. Med. Chem. 2000, 43, 4552.
  (b) Selent, J.; Brandt, W.; Pamperin, D.; Goeber, B. Bioorg. Med. Chem. 2006, 14, 1729.
37. [37]
  Duan, H. F.; Xie, J. H. Qiao, X. C. Wang, L. X.; Zhou, Q. L. Angew. Chem., Int. Ed. 2008, 47, 4351. doi: 10.1002/anie.200800423
38. [38]
  Cai, F.; Pu, X. T.; Qi, X. B.; Lynch, V.; Radha, A.; Ready, J. M. J. Am. Chem. Soc. 2011, 133, 18066. doi: 10.1021/ja207748r
39. [39]
  (a) Zhu, T.-S.; Jin, S.-S.; Xu, M.-H. Angew. Chem., Int. Ed. 2012, 51, 780.
  (b) Wang, H.; Zhu, T.-S.; Xu, M.-H. Org. Biomol. Chem. 2012, 10, 9158.
40. [40]
  Li, Y.; Zhu, D.-X.; Xu, M.-H. Chem. Commun. 2013, 49, 11659. doi: 10.1039/c3cc47927g
41. [41]
  Zhu, T.-S.; Xu, M.-H. Chin. J. Chem. 2013, 31, 321. doi: 10.1002/cjoc.201300063
42. [42]
  Melcher, M.-C.; Ivšić, T.; Olagnon, C.; Tenten, C.; Letzen, A.; Strand, D. Chem.-Eur. J. 2018, 24, 2344. doi: 10.1002/chem.201704816
43. [43]
  Chang, C.-A.; Uang, T.-Y.; Jian, J.-H.; Zhou, M.-Y.; Chen, M.-L.; Kuo, T.-S.; Wu, P.-Y.; Wu, H.-L. Adv. Synth. Catal. 2018, 360, 3381. doi: 10.1002/adsc.201800575
44. [44]
  Bartlett, S. L.; Keiter, K. M.; Johnson, J. S. J. Am. Chem. Soc. 2017, 139, 3911. doi: 10.1021/jacs.7b00943
45. [45]
  Jung, J. K.; Johnson, B. R.; Duong, T.; Decaire, M.; Uy, J.; Gharbaoui, T.; Boatman, P. D.; Sage, C. R.; Chen, R.; Richman, J. G.; Connolly, D. T.; Semple, G. J. Med. Chem. 2007, 50, 1445. doi: 10.1021/jm070022x
46. [46]
  Singh, S. B.; Zink, D. L.; Quamina, D. S.; Pelaez, F.; Teran, A.; Felock, P.; Hazuda, D. J. Tetrahedron Lett. 2002, 43, 2351. doi: 10.1016/S0040-4039(02)00265-4
47. [47]
  Feng, X.; Nie, Y.; Yang, J.; Du, H. Org. Lett. 2012, 14, 624. doi: 10.1021/ol203238j
48. [48]
  Wen, Q.; Zhang, L.; Xiong, J.; Zeng, Q. L. Eur. J. Org. Chem. 2016, 5360.
49. [49]
  Zhu, T.-S.; Chen, J.-P.; Xu, M.-H. Chem. Eur. J. 2013, 19, 865. doi: 10.1002/chem.201203701
50. [50]
  Zhang, Z.-F.; Zhu, D.-X.; Chen, W.-W.; Xu, B.; Xu, M.-H. Org. Lett. 2017, 19, 2726. doi: 10.1021/acs.orglett.7b01070
51. [51]
  Yu, Y.-N.; Xu, M.-H. Org. Chem. Front. 2014, 1, 738. doi: 10.1039/C4QO00135D
52. [52]
  (a) Rowley, M.; Hallett, D. J.; Goodacre, S.; Moyes, C.; Crawforth, J.; Sparey, T. J.; Patel, S.; Marwood, R.; Thomas, S.; Hitzel, L.; O'Connor, D.; Szeto, N.; Castro, J. L.; Hutson, P. H.; MacLeod, A. M. J. Med. Chem. 2001, 44, 1603.
  (b) van Niel, M. B.; Collins, I.; Beer, M. S.; Broughton, H. B.; Cheng, S. K.; Goodacre, S. C.; Heald, A.; Locker, K. L.; MacLeod, A. M.; Morrison, D.; Moyes, C. R.; O'Connor, D.; Pike, A.; Rowley, M.; Russell, M. G.; Sohal, B.; Stanton, J. A.; Thomas, S.; Verrier, H.; Watt, A. P.; Castro, J. L. J. Med. Chem. 1999, 42, 2087.
  (c) Domagala, J. M.; Hanna, L. D.; Heifetz, C. L.; Hutt, M. P.; Mich, T. F.; Sanchez, J. P.; Solomon, M. J. Med. Chem. 1986, 29, 394.
  (d) Rosenblum, S. B.; Huynh, T.; Afonso, A.; Davis, H. R. Jr.; Yumibe, N.; Clader, J. W.; Burnett, D. A. J. Med. Chem. 1998, 41, 973.
53. [53]
  Martina, S. L. X.; Jagt, R. B. C.; Vries, J. G.; Feringa B. L.; Minnaard, A. J. Chem. Commun. 2006, 42, 4093.
54. [54]
  Jumde, V. R.; Facchetti, S.; Iuliano, A. Tetrahedron: Asymmetry 2010, 21, 2775. doi: 10.1016/j.tetasy.2010.11.009
55. [55]
  Luo, R. S.; Li, K.; Hu, Y. L.; Tang, W. J. Adv. Synth. Catal. 2013, 355, 1297. doi: 10.1002/adsc.201201125
56. [56]
  Korenaga, T.; Ko, A.; Uotani, K.; Tanaka, Y.; Sakai, T. Angew. Chem., Int. Ed. 2011, 50, 10703. doi: 10.1002/anie.201104588
57. [57]
  Liao, Y. X.; Xing, C. H.; Hu, Q. S. Org. Lett. 2012, 14, 1544. doi: 10.1021/ol300275s
58. [58]
  Huang, L. W.; Zhu, J. B.; Jiao, G. J.; Wang, Z.; Yu, X. X.; Deng, W. P.; Tang, W. J. Angew. Chem., Int. Ed. 2016, 55, 4527. doi: 10.1002/anie.201600979
59. [59]
  Bouffard, J.; Itami, K. Org. Lett. 2009, 11, 4410. doi: 10.1021/ol9017613
60. [60]
  Liu, G. X.; Lu, X. Y. J. Am. Chem. Soc. 2006, 128, 16504. doi: 10.1021/ja0672425
61. [61]
  Gallego, G. M.; Sarpong, R. Chem. Sci. 2012, 3, 1338. doi: 10.1039/c2sc01068b
62. [62]
  Low, D. W.; Pattison, G.; Wieczysty, M. D.; Churchill, G. H.; Lam, H. W. Org. Lett. 2012, 14, 2548. doi: 10.1021/ol300845q
63. [63]
  Zhu, D.-X.; Chen, W.-W.; Xu, M.-H. Tetrahedron 2016. 72, 2037.
64. [64]
  Chen, D.; Xu, M.-H. Chin. J. Org. Chem. 2017, 37, 1589 (in Chinese).
1. [1]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
2. [2]
  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
3. [3]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
4. [4]
  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
5. [5]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
6. [6]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
7. [7]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
8. [8]
  Qianwen Han , Tenglong Zhu , Qiuqiu Lü , Mahong Yu , Qin Zhong . 氢电极支撑可逆固体氧化物电池性能及电化学不对称性优化. Acta Physico-Chimica Sinica, 2025, 41(1): 2309037-. doi: 10.3866/PKU.WHXB202309037
9. [9]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
10. [10]
  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
11. [11]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
12. [12]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
13. [13]
  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
14. [14]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
15. [15]
  Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . 二维共价有机框架作为光催化剂在有机合成中的研究进展. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-. doi: 10.1016/j.actphy.2025.100086
16. [16]
  Wenjie SHI , Fan LU , Mengwei CHEN , Jin WANG , Yingfeng HAN . Synthesis and host-guest properties of imidazolium-functionalized zirconium metal-organic cage. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 105-113. doi: 10.11862/CJIC.20240360
17. [17]
  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
18. [18]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
19. [19]
  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
20. [20]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379

Get Citation

PDF

XML

Metrics

PDF Downloads(85)
Abstract views(5571)
HTML views(956)

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