Citation: Zhu Ren-Yi, Liao Kui, Yu Jin-Sheng, Zhou Jian. Recent Advances in Catalytic Asymmetric Synthesis of P-Chiral Phosphine Oxides[J]. Acta Chimica Sinica, ;2020, 78(3): 193-216. doi: 10.6023/A20010002 shu

Recent Advances in Catalytic Asymmetric Synthesis of P-Chiral Phosphine Oxides

Zhu Ren-Yi ^a ,
Liao Kui ^a ,
Yu Jin-Sheng ^a,, ,
Zhou Jian ^a,b,,

a.
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062
b.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, Shanghai 200032

Corresponding author: Yu Jin-Sheng, jsyu@chem.ecnu.edu.cn Zhou Jian, jzhou@chem.ecnu.edu.cn
Received Date: 1 January 2020
Available Online: 21 February 2020
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21725203, 21901074)the National Natural Science Foundation of China 21901074the National Natural Science Foundation of China 21725203

Figures(35)

P-Chiral phosphine oxides are a class of privileged structures, which have important applications in the field of medicinal chemistry, organic synthesis, life and material science. Recent years have witnessed significant progress in the catalytic asymmetric construction of such scaffolds. These advances are summarized in this review according to the following three major strategies:desymmetrization of prochiral tertiary phosphine oxides, (dynamic) kinetic resolution of tertiary phosphine oxides, and catalytic asymmetric reactions involving secondary phosphine oxides, and discusses the possible reaction mechanism, the advantage and disadvantage of each type of reactions, which would provide reference and inspiration for the researchers engaged in organic synthesis and organic phosphorus chemistry.
- P-chiral phosphine oxide,
- catalytic asymmetric synthesis,
- desymmetrization,
- (dynamic) kinetic resolution,
- tertiary phosphine oxide,
- secondary phosphine oxide
1. [1]
  (a) Dutartre, M.; Bayardon, J.; Jugé, S. Chem. Soc. Rev. 2016, 45, 5771. (b) Macia, E. Chem. Soc. Rev. 2005, 34, 691.
2. [2]
  (a) Kazemi, M.; Tahmasbi, A. M.; Valizadeh, R.; Naserian, A. A.; Soni, A. Agric. Sci. Res. J. 2012, 2, 512. (b) Lamberth, C. Tetrahedron 2010, 66, 7239.
3. [3]
  De Clercq, E. Clin. Microbiol. Rev. 2003, 16, 569. doi: 10.1128/CMR.16.4.569-596.2003
4. [4]
  (a) Akiyama, T. Chem. Rev. 2007, 107, 5744. (b) Milo, A.; Neel, A. J.; Toste, F. D.; Sigman, M. S. Science 2015, 347, 737.
5. [5]
  Duffy, M. P.; Delaunay, W.; Bouit, P.-A.; Hissler, M. Chem. Soc. Rev. 2016, 45, 5296. doi: 10.1039/C6CS00257A
6. [6]
  Ohmaru, Y.; Sato, N.; Mizutani, M.; Kotani, S.; Sugiura, M.; Nakajima, M. Org. Biomol. Chem. 2012, 10, 4562. doi: 10.1039/c2ob25338k
7. [7]
  Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
8. [8]
  Xu, B.; Zhu, S.-F.; Xie, X.-L, Shen, J.-J.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2011, 50, 11483. doi: 10.1002/anie.201105485
9. [9]
  Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207. doi: 10.1021/ja970654g
10. [10]
  Schulze, C. J.; Navarro, G.; Ebert, D.; DeRisi, J.; Linington, R. G. J. Org. Chem. 2015, 80, 1312. doi: 10.1021/jo5024409
11. [11]
  Cholongitas, E.; Papatheodoridis, G. V. Ann. Gastroenterol. 2014, 27, 331.
12. [12]
  Clarion, L.; Jacquard, C.; Sainte-Catherine, O.; Loiseau, S.; Filippini, D.; Hirlemann, M.-H.; Volle, J.-N.; Virieux, D.; Lecouvrey, M.; Pirat, J.-L.; Bakalara, N. J. Med. Chem. 2012, 55, 2196. doi: 10.1021/jm201428a
13. [13]
  (a) Baraniak, J.; Kinas, R. W.; Lesiak, K.; Stec, W. J. J. Chem. Soc. 1979, 940. (b) Dostmann, W. R. G.; Taylor, S. S.; Genieser, H.-G.; Jastorff, B.; Døskeland, S. O.; Øgreid, D. J. Biol. Chem. 1990, 265, 10484.
14. [14]
  Matsukawa, M.; Sugama, H.; Imamoto, T. Tetrahedron Lett. 2000, 41, 6461. doi: 10.1016/S0040-4039(00)01030-3
15. [15]
  (a) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kobayashi, Y. Tetrahedron Lett. 1996, 37, 5149. (b) Iseki, K.; Kuroki, Y.; Takahashi, M.; Kishimoto, S. Tetrahedron 1997, 53, 3513.
16. [16]
  Xu, G.; Senanayake, C. H.; Tang, W. Acc. Chem. Res. 2019, 52, 1101. doi: 10.1021/acs.accounts.9b00029
17. [17]
  Selected examples using P-chiral phosphines as ligands: (a) Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946. (b) Gridnev, I. D.; Higashi, N.; Asakura, K.; Imamoto, T. J. Am. Chem. Soc. 2000, 122, 7183. (c) Tang, W.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 1612. (d) Taylor, A. M.; Altman, R. A.; Buchwald S. L. J. Am. Chem. Soc. 2009, 131, 9900. (e) Imamoto, T.; Tamura, K.; Zhang, Z.; Horiuchi, Y.; Sugiya, M.; Yoshida, K.; Yanagisawa, A.; Gridnev, I. D. J. Am. Chem. Soc. 2012, 134, 1754. (f) Liu, G.; Liu, X.; Cai, Z.; Jiao, G.; Xu, G.; Tang, W. Angew. Chem., Int. Ed. 2013, 52, 4235. Selected examples using P-chiral phosphine as organocatalysts: (g) Sampath, M.; Loh, T.-P. Chem. Sci. 2010, 1, 739. (h) Rémond, E.; Bayardon, J.; Takizawa, S.; Rousselin, Y.; Sasai; H.; Jugé, S. Org. Lett. 2013, 15, 1870. (i) Takizawa, S.; Rémond, E.; Arteaga, F.; Yoshida, Y.; Sridharan, V.; Bayardon, J.; Jugé, S.; Sasai, H. Chem. Commun. 2013, 49, 8392. (j) Henry, C. E.; Xu, Q.-H.; Fan, Y.-C.; Martin, T. J.; Belding, L.; Dudding, T.; Kwon, O. J. Am. Chem. Soc. 2014, 136, 11890.
18. [18]
19. [19]
  Selected examples for chiral resolution: see ref. 17a, and (a) Korpiun, O.; Lewis, R. A.; Chickos, J.; Mislow, K. J. Am. Chem. Soc. 1968, 90 4842. For chiral auxiliaries: (b) Berger, O.; Montchamp, J.-L. Angew. Chem., Int. Ed. 2013, 52, 11377. (c) Han, Z. S.; Goyal, N.; Herbage, M. A.; Sieber, J. D.; Qu, B.; Xu, Y.; Li, Z.; Reeves, J. T.; Desrosiers, J.-N.; Ma, S.; Grinberg, N.; Lee, H.; Mangunuru, H. P. R.; Zhang, Y.; Krishnamurthy, D.; Lu, B. Z.; Song, J. J.; Wang, G.; Senanayake, C. H. J. Am. Chem. Soc. 2013, 135, 2474. (d) Gwon, D.; Lee, D.; Kim, J.; Park, S.; Chang, S. Chem. Eur. J. 2014, 20, 12421. For asymmetric oxidation of tertiary phosphines: (e) Bergin, E.; O'Connor, C. T.; Robinson, S. B.; McGarrigle, E. M.; O'Mahony, C. P.; Gilheany, D. G. J. Am. Chem. Soc. 2007, 129 9566. (f) Rajendran, K. V.; Kennedy, L.; Gilheany, D. G. Eur. J. Org. Chem. 2010, 5642. (g) Nikitin, K.; Rajendran, K. V.; Müller-Bunz, H.; Gilheany, D. G. Angew. Chem., Int. Ed. 2014, 53, 1906.
20. [20]
  (a) Zeng, X.-P.; Cao, Z.-Y.; Wang, Y.-H.; Zhou, F.; Zhou, J. Chem. Rev. 2016, 116, 7330. (b) Petersen, K. S. Tetrahedron Lett. 2015, 56, 6523. (c) Willis, M. C. J. Chem. Soc., Perkin Trans. 1 1999, 1765.
21. [21]
  Nishida, G.; Noguchi, K.; Hirano, M.; Tanaka, K. Angew. Chem., Int. Ed. 2008, 47, 3410. doi: 10.1002/anie.200800144
22. [22]
  Zheng, Y.; Guo, L.; Zi, W. Org. Lett. 2018, 20, 7039. doi: 10.1021/acs.orglett.8b02982
23. [23]
  Zhang, Y.; Zhang, F.; Chen, L.; Xu, J.; Liu, X.; Feng, X. ACS Catal. 2019, 9, 4834. doi: 10.1021/acscatal.9b00860
24. [24]
  Zhu, R. Y.; Chen, L.; Hu, X. S.; Zhou, F.; Zhou, J. Chem. Sci. 2020, 11, 97. doi: 10.1039/C9SC04938J
25. [25]
  (a) Meng, J.-C.; Fokin, V. V.; Finn, M. G. Tetrahedron Lett. 2005, 46, 4543. (b) Stephenson, G. R.; Buttress, J. P.; Deschamps, D.; Lancelot, M.; Martin, J. P.; Sheldon, A. I. G.; Alayrac, C.; Gaumont, A.-C.; Page, P. C. B. Synlett 2013, 24, 2723. (c) Song, T.; Li, L.; Zhou, W.; Zheng, Z.-J.; Deng, Y.; Xu, Z.; Xu, L.-W. Chem. Eur. J. 2015, 21, 554. (d) Chen, M.-Y.; Song, T.; Zheng, Z.-J.; Xu, Z.; Cui, Y.-M.; Xu, L.-W. RSC Adv. 2016, 6, 58698. (e) Chen, M.-Y.; Xu, Z.; Chen, L.; Song, T.; Zheng, Z.-J.; Cao, J.; Cui, Y.-M., Xu, L.-W. ChemCatChem 2018, 10, 280. For achiral version: (f) Rodionov, V. O.; Fokin, V. V.; Finn, M. G. Angew. Chem., Int. Ed. 2005, 44, 2210.
26. [26]
  (a) Worrell, B. T.; Malik, J. A.; Fokin, V. V. Science 2013, 340, 457. (b) Díez, J.; Gamasa, M. P.; Panera, M. Inorg. Chem. 2006, 45, 10043.
27. [27]
  Zhou, F.; Tan, C.; Tang, J.; Zhang, Y.-Y.; Gao, W.-M.; Wu, H.-H.; Yu, Y.-H.; Zhou, J. J. Am. Chem. Soc. 2013, 135 10994. doi: 10.1021/ja4066656
28. [28]
  (a) Osako, T.; Uozumi, Y. Org. Lett. 2014, 16, 5866. (b) Osako, T.; Uozumi, Y. Synlett 2015, 26, 1475.
29. [29]
  For reviews: (a) Ren, Y.; Baumgartner, T. Dalton Trans. 2012, 41, 7792. (b) Matano, Y.; Imahori, H. Org. Biomol. Chem. 2009, 7, 1258. For recent examples: (c) Stolar, M.; Borau-Garcia, J.; Toonen, M.; Baumgartner, T. J. Am. Chem. Soc. 2015, 137, 3366. (d) Yamaguchi, E.; Wang, C.; Fukazawa, A.; Taki, M.; Sato, Y.; Sasaki, T.; Ueda, M.; Sasaki, N.; Higashiyama, T.; Yamaguchi, S. Angew. Chem., Int. Ed. 2015, 54, 4539. (e) Reus, C.; Stolar, M.; Vanderkley, J.; Nebauer, J.; Baumgartner, T. J. Am. Chem. Soc. 2015, 137, 11710.
30. [30]
  Tahara, Y.-K.; Sato, T.; Matsubara, R.; Kanyiva, K. S.; Shibata, T. Heterocycles 2016, 93, 685. doi: 10.3987/COM-15-S(T)57
31. [31]
  Harvey, J. S.; Malcolmson, S. J.; Dunne, K. S.; Meek, S. J.; Thompson, A. L.; Schrock, R. R.; Hoveyda, A. H.; Gouverneur, V. Angew. Chem., Int. Ed. 2009, 48, 762. doi: 10.1002/anie.200805066
32. [32]
  Wang, Z.; Hayashi. T. Angew. Chem., Int. Ed. 2018, 57, 1702. doi: 10.1002/anie.201712572
33. [33]
  For selected reviews on C-H bond functionalization, see: (a) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826. (b) Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242. (c) Xu, L.-M.; Li, B.-J.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712. (d) Albrecht, M. Chem. Rev. 2010, 110, 576. (e) Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651. (f) Newton, C. G.; Wang, S.-G.; Oliveira, C. C.; Cramer, N. Chem. Rev. 2017, 117, 8908.
34. [34]
  Du, Z.-J.; Guan, J.; Wu, G.-J.; Xu, P.; Gao, L.-X.; Han, F.-S. J. Am. Chem. Soc. 2015, 137, 632. doi: 10.1021/ja512029x
35. [35]
  Guan, J.; Wu, G.-J.; Han, F.-S. Chem. Eur. J. 2014, 20, 3301. doi: 10.1002/chem.201303056
36. [36]
  (a) Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882. (b) Shi, B.-F.; Zhang, Y.-H.; Lam, J.-K.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 460. (c) Yang, Y.-F.; Hong, X.; Yu, J.-Q.; Houk, K. N. Acc. Chem. Res. 2017, 50, 2853.
37. [37]
  Sun, Y.; Cramer, N. Angew. Chem., Int. Ed. 2017, 56, 364. doi: 10.1002/anie.201606637
38. [38]
  Gwon, D.; Park, S.; Chang, S. Tetrahedron 2015, 71, 4504. doi: 10.1016/j.tet.2015.02.065
39. [39]
  Jang, Y.-S.; Dieckmann, M.; Cramer, N. Angew. Chem., Int. Ed. 2017, 56, 15088.
40. [40]
  Jang, Y.-S.; Woźniak, Ł.; Pedroni, J.; Cramer, N. Angew. Chem., Int. Ed. 2018, 57, 12901. doi: 10.1002/anie.201807749
41. [41]
  Lin, Z.-Q.; Wang, W.-Z.; Yan, S.-B.; Duan, W.-L. Angew. Chem., Int. Ed. 2015, 54, 6265. doi: 10.1002/anie.201500201
42. [42]
  Liu, L.; Zhang, A.-A.; Wang, Y.; Zhang, F.; Zuo, Z.; Zhao, W.-X.; Feng, C.-L.; Ma, W. Org. Lett. 2015, 17, 2046. doi: 10.1021/acs.orglett.5b00122
43. [43]
  Lin, Y.; Ma, W.-Y.; Sun, Q.-Y.; Cui, Y.-M.; Xu, L.-W. Synlett 2017, 28, 1432. doi: 10.1055/s-0036-1588983
44. [44]
  Li, Z.; Lin, Z.-Q.; Yan, C.-G.; Duan, W.-L. Organometallics 2019, 38, 3916. doi: 10.1021/acs.organomet.9b00216
45. [45]
  Xu, G. Q.; Li, M. H.; Wang, S. L.; Tang, W. J. Org. Chem. Front. 2015, 2, 1342. doi: 10.1039/C5QO00142K
46. [46]
  Huang, Z.; Huang, X.; Li, B.; Mou, C.; Yang, S.; Song, B.-A.; Chi, Y. R. J. Am. Chem. Soc. 2016, 138, 7524. doi: 10.1021/jacs.6b04624
47. [47]
  Yang, G.-H.; Li, Y.; Li, X.; Cheng, J.-P. Chem. Sci. 2019, 10, 4322.
48. [48]
  Toda, Y.; Pink, M.; Johnston, J. N. J. Am. Chem. Soc. 2014, 136, 14734. doi: 10.1021/ja5088584
49. [49]
  Dobish, M. C.; Johnston, J. N. J. Am. Chem. Soc. 2011, 134, 6068.
50. [50]
  Trost, B. M.; Spohr, S. M.; Rolka, A. B.; Kalnmals, C. A. J. Am. Chem. Soc. 2019, 141, 14098. doi: 10.1021/jacs.9b07340
51. [51]
  Liu, S.; Zhang, Z. F.; Xie, F.; Butt, N. A.; Sun, L.; Zhang, W. B. Tetrahedron Asymmetry 2012, 23, 329. doi: 10.1016/j.tetasy.2012.02.018
52. [52]
  Sun, Y.; Cramer, N. Chem. Sci. 2018, 9, 2981. doi: 10.1039/C7SC05411D
53. [53]
  Lim, K. M.-H.; Hayashi, T. J. Am. Chem. Soc. 2017, 139, 8122. doi: 10.1021/jacs.7b04570
54. [54]
  Emmick, T. L.; Letsinger, R. L. J. Am. Chem. Soc. 1968, 90, 3459. doi: 10.1021/ja01015a030
55. [55]
  Fu, X.; Loh, W.-T.; Zhang, Y.; Chen, T.; Ma, T.; Liu, H.; Wang, J.; Tan, C.-H. Angew. Chem., Int. Ed. 2009, 48, 7387. doi: 10.1002/anie.200903971
56. [56]
  Xie, P. Z.; Guo, L.; Xu, L. L.; Loh, T.-P. Chem. Asian J. 2016, 11, 1353. doi: 10.1002/asia.201600108
57. [57]
  (a) Zhang, H.; Sun, Y.-M.; Yao, L.; Ji, S.-Y.; Zhao, C.-Q.; Han, L.-B. Chem. Asian J. 2014, 9, 1329. (b) Wang, J.-P.; Nie, S.-Z.; Zhou, Z.-Y.; Ye, J.-J.; Wen, J.-H.; Zhao, C.-Q. J. Org. Chem. 2016, 81, 7644.
58. [58]
  Du, J.-Y.; Ma, Y.-H.; Yuan, R.-Q.; Xin, N. N.; Nie, S.-Z.; Ma, C.-L.; Li, C.-Z.; Zhao, C.-Q. Org. Lett. 2018, 20, 477. doi: 10.1021/acs.orglett.7b03863
59. [59]
  Beaud, R.; Phipps, R. J.; Gaunt, M. J. J. Am. Chem. Soc. 2016, 138, 13183. doi: 10.1021/jacs.6b09334
60. [60]
  Zhang, Y.; He, H.; Wang, Q. Y.; Cai, Q. Tetrahedron Lett. 2016, 57, 5308. doi: 10.1016/j.tetlet.2016.10.048
61. [61]
  Dai, Q.; Li, W.-B.; Li, Z.-M.; Zhang, J.-L. J. Am. Chem. Soc. 2019, 141, 20556. doi: 10.1021/jacs.9b11938
62. [62]
  Liu, X.-T.; Zhang, Y.-Q.; Han, X.-Y.; Sun, S.-P.; Zhang, Q.-W. J. Am. Chem. Soc. 2019, 141, 16584. doi: 10.1021/jacs.9b08734
1. [1]
  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
2. [2]
  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
3. [3]
  Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO₂-0.39IrO_x composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
4. [4]
  Ping ZHANG , Chenchen ZHAO , Xiaoyun CUI , Bing XIE , Yihan LIU , Haiyu LIN , Jiale ZHANG , Yu'nan CHEN . Preparation and adsorption-photocatalytic performance of ZnAl@layered double oxides. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1965-1974. doi: 10.11862/CJIC.20240014
5. [5]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
6. [6]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
7. [7]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
8. [8]
  Xin Han , Zhihao Cheng , Jinfeng Zhang , Jie Liu , Cheng Zhong , Wenbin Hu . Design of Amorphous High-Entropy FeCoCrMnBS (Oxy) Hydroxides for Boosting Oxygen Evolution Reaction. Acta Physico-Chimica Sinica, 2025, 41(4): 100033-. doi: 10.3866/PKU.WHXB202404023
9. [9]
  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
10. [10]
  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
11. [11]
  Endong YANG , Haoze TIAN , Ke ZHANG , Yongbing LOU . Efficient oxygen evolution reaction of CuCo₂O₄/NiFe-layered bimetallic hydroxide core-shell nanoflower sphere arrays. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 930-940. doi: 10.11862/CJIC.20230369
12. [12]
  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
13. [13]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
14. [14]
  Xueyu Lin , Ruiqi Wang , Wujie Dong , Fuqiang Huang . 高性能双金属氧化物负极的理性设计及储锂特性. Acta Physico-Chimica Sinica, 2025, 41(3): 2311005-. doi: 10.3866/PKU.WHXB202311005
15. [15]
  Xiaotian ZHU , Fangding HUANG , Wenchang ZHU , Jianqing ZHAO . Layered oxide cathode for sodium-ion batteries: Surface and interface modification and suppressed gas generation effect. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 254-266. doi: 10.11862/CJIC.20240260
16. [16]
  Junli Liu . Practice and Exploration of Research-Oriented Classroom Teaching in the Integration of Science and Education: a Case Study on the Synthesis of Sub-Nanometer Metal Oxide Materials and Their Application in Battery Energy Storage. University Chemistry, 2024, 39(10): 249-254. doi: 10.12461/PKU.DXHX202404023
17. [17]
  Yaping ZHANG , Tongchen WU , Yun ZHENG , Bizhou LIN . Z-scheme heterojunction β-Bi₂O₃ pillared CoAl layered double hydroxide nanohybrid: Fabrication and photocatalytic degradation property. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 531-539. doi: 10.11862/CJIC.20240256
18. [18]
  You Wu , Chang Cheng , Kezhen Qi , Bei Cheng , Jianjun Zhang , Jiaguo Yu , Liuyang Zhang . ZnO/D-A共轭聚合物S型异质结高效光催化产H₂O₂及其电荷转移动力学研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406027-. doi: 10.3866/PKU.WHXB202406027
19. [19]
  Yan LIU , Jiaxin GUO , Song YANG , Shixian XU , Yanyan YANG , Zhongliang YU , Xiaogang HAO . Exclusionary recovery of phosphate anions with low concentration from wastewater using a CoNi-layered double hydroxide/graphene electronically controlled separation film. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1775-1783. doi: 10.11862/CJIC.20240043
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(204)
Abstract views(5144)
HTML views(1309)

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