Citation: Wei Liang, Xiao Lu, Hu Yuanzheng, Wang Zuofei, Tao Haiyan, Wang Chunjiang. Recent Advances in Metallated Azomethine Ylides for the Synthesis of Chiral Unnatural α-Amino Acids[J]. Chinese Journal of Organic Chemistry, ;2019, 39(8): 2119-2130. doi: 10.6023/cjoc201904060 shu

Recent Advances in Metallated Azomethine Ylides for the Synthesis of Chiral Unnatural α-Amino Acids

Wei Liang ^a ,
Xiao Lu ^a ,
Hu Yuanzheng ^a ,
Wang Zuofei ^a ,
Tao Haiyan ^a ,
Wang Chunjiang ^a,b,,

a.
Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072
b.
State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071

Corresponding author: Wang Chunjiang, cjwang@whu.edu.cn
Received Date: 24 April 2019
Revised Date: 25 May 2019
Available Online: 3 August 2019
Fund Project: Project supported by the National Natural Science Foundation of China 21772147Project supported by the National Natural Science Foundation of China 21525207the China Postdoctoral Science Foundation 2017M620331Project supported by the National Natural Science Foundation of China (Nos. 21525207, 21772147) and the China Postdoctoral Science Foundation (No. 2017M620331)

Figures(22)

The development of efficient methods for the preparation of unnatural amino acids has long been an important goal since their widely application in synthetic and medicinal chemistry. The asymmetric α-functionalization of nucleophilic metalated azomethine ylides, which could be in situ-generated from readily-available aldimine esters, has been recogonized as a powerful strategy to synthesize unnatural amino acids. Over the past 20 years, tranistion metal-catalyzed asymmetric construction of unnatural amino acids using azomethine ylides have been extensively studied. In this review, the progress on metallated azomethine ylides invovled aymmetric transformation for the synthesis of unnatural amino acids is summarized according to eletrophilic reagents.
- azomethine ylide,
- asymmetric catalysis,
- unnatural α-amino acid
1. [1]
  Wu, W. T. Biochemistry, People's Medical Publishing House, Beijing, 2004, pp. 39~42(in Chinese).
2. [2]
  (a) Bellier, B.; McCort-Tranchenpain, I.; Ducos, B.; Danascimento, S.; Meudal, H.; Noble, F.; Garbay, C.; Roques, B. P. J. Med. Chem. 1997, 40, 3947.
  (b) Dery, O.; Josien, H.; Grassi, J.; Chassaing, G.; Couraud, J. Y.; Lavielle, S. Biopolymers 1996, 39, 67.
  (c) Benedetti, E.; Gavuzzo, E.; Santini, A.; Kent, D. R.; Zhu, Y.-F.; Zhu, Q.; Mahr, C.; Goodman, M. J. Pept. Sci. 1995, 1, 349.
  (d) Schiller, P. W.; Weltrowska, G.; Nguyen, T. M.-D.; Lemieux, C.; Chung, N. N.; Marsden, B. J.; Wilkes, B. C. J. Med. Chem. 1991, 34, 3125.
3. [3]
  (a) Koert, U. Nachr. Chem. Technol. Lab. 1995, 43, 347.
  (b) Yano, S.; Nakanishi, Y.; Ikuina, Y.; Ando, K.; Yoshida, M.; Saitoh, Y.; Matsuda, Y.; Bando, C. J. Antibiot. 1997, 50, 992.
  (c) Kende, A. S.; Liu, K.; Jos Brands, K. M. J. Am. Chem. Soc. 1995, 117, 10597.
4. [4]
  (a) Ohfune, Y.; Shinada, T. Eur. J. Org. Chem. 2005, 5127.
  (b) Vogt, H.; Brase, S. Org. Biomol. Chem. 2007, 5, 406.
  (c) Bera, K.; Namboothiri, I. N. N. Asian J. Org. Chem. 2014, 3, 1234.
5. [5]
  (a) Adrio, J.; Carretero, J. C. Chem. Commun. 2014, 50, 12434.
  (b) O'Donnell, M. J. Acc. Chem. Res. 2004, 37, 506.
  (c) Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10.
  (d) Lygo, B.; Andrews, B. I. Acc. Chem. Res. 2004, 37, 518.
  (e) Maruoka, K.; Ooi, T.; Kano, T. Chem. Commun. 2007, 1487.
  (f) Kazmaier, U. Org. Chem. Front. 2016, 3, 1541.
  (f) Tang, S.; Zhang, X.; Sun, J.; Niu, D.; Chruma, J. J. Chem. Rev. 2018, 118, 10393.
6. [6]
  (a) Saito, S.; Tsubogo, T.; Kobayashi, S. J. Am. Chem. Soc. 2007, 129, 5364.
  (b) Tsubogo, T.; Saito, S.; Seki, K.; Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2008, 130, 13321.
7. [7]
  (a) Li, Q.; Ding, C.-H.; Hou, X.-L.; Dai, L.-X. Org. Lett. 2010, 12, 1080.
  (b) Strohmeier, M.; Leach, K.; Zajac, M. A. Angew. Chem., Int. Ed. 2011, 50, 12335.
  (c) Hernández-Toribio, J.; Arrayás, R. G.; Carretero, J. C. Chem. Eur. J. 2011, 17, 6334.
  (d) He, F.-S.; Jin, J.-H.; Yang. Z.-T.; Yu, X.; Fessey, J. S.; Deng, W.-P. ACS Catal. 2016, 6, 652.
  (e) Konno, T.; Watanabe, S; Takahashi, T.; Tokoro, Y.; Fukuzawa, S. Org. Lett. 2013, 15, 4418.
  (f) Imae, K.; Konno, T.; Ogata, K.; Fukuzawa, S. Org. Lett. 2012, 13, 4410.
8. [8]
  (a) Koizumi, A.; Kimura, M.; Arai, Y.; Tokoro, Y.; Fukuzawa, S. J. Org. Chem. 2015, 80, 10883;
  (b) Matsuda, Y.; Koizumi, A.; Haraguchi, R.; Fukuzawa, S. J. Org. Chem. 2016, 81, 7939;
  (c) Koizumi, A.; Matsuda, Y.; Haraguchi, R.; Fukuzawa, S. Tetrahedron: Asymmetry 2017, 28, 428;
  (d) Xue, Z.-Y.; Song, Z.-M.; Wang, C.-J. Org. Biomol. Chem. 2015, 13, 5460.
9. [9]
  Xue, Z.-Y.; Liu, T.-L.; Lu, Z.; Huang, H.; Tao, H.-Y.; Wang, C.-J. Chem. Commun. 2010, 46, 1727. doi: 10.1039/b919625k
10. [10]
  Xue, Z.-Y.; Li, Q.-H.; Tao, H.-Y.; Wang, C.-J. J. Am. Chem. Soc. 2011, 133, 11757. doi: 10.1021/ja2043563
11. [11]
  Wang, M.; Wang, C.-J. Lin, Z. Organometallics 2012, 31, 7870. doi: 10.1021/om300435s
12. [12]
  Teng, H.-L.; Luo, F.-L.; Tao, H.-T.; Wang, C.-J. Org. Lett. 2011, 13, 5600. doi: 10.1021/ol202326j
13. [13]
  (a) Panday, S. K.; Prasad, J.; Dikshit, D. K. Tetrahedron: Asymmetry 2009, 20, 1581.
  (b) Smith, M. B. Alkaloids: Chem. Biol. Perspect. 1998, 12, 229.
  (c) Benoit, R.; Pascal, C.; Dominique, F.; Francois, S. Trends Heterocycl. Chem. 1991, 2, 155.
14. [14]
  Teng, H.-L.; Huang, H.; C.-J. Chem. Eur. J. 2012, 18, 12614. doi: 10.1002/chem.201201475
15. [15]
  (a) Mori, T.; Takahashi, K.; Kashiwabara, M.; Uemura, D. Tetrahedron Lett. 1985, 26, 1073;
  (b) Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113;
  (c) S. Omura, K.; Matsuzaki, T.; Fujimoto, K.; Kosuge, T.; Furuya, S.; Fujita, A. J. Antibiot. 1991, 44, 117.
16. [16]
  Kim, H. Y.; Li, J.-Y.; Kim, S.; Oh, K. J. Am. Chem. Soc. 2011, 133, 20750. doi: 10.1021/ja2100356
17. [17]
  Bai, X.-F.; Li, L.; Xu, Z.; Zheng, Z.-J.; Xia, C.-G.; Xu, L.-W. Chem. Eur. J. 2016, 18, 10339.
18. [18]
  Yuan, Y.; Yu, B.; Bai, X.-F.; Xu, Z.; Zheng, Z.-J.; Cui, Y.-M.; Cao, J.; Xu, L.-W. Org. Lett. 2017, 19, 4896. doi: 10.1021/acs.orglett.7b02378
19. [19]
  Bernardi, L.; Gothelf, A. S.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 2583. doi: 10.1021/jo026766u
20. [20]
  Yan, X.-X.; Peng, Q.; Li, Q.; Zhang, K.; Yao, J.; Hou, X.-L.; Wu, Y.-D. J. Am. Chem.Soc. 2008, 130, 14362. doi: 10.1021/ja804527r
21. [21]
  (a) Arai, T.; Mishiro, A.; Matsumura, E.; Awata, A.; Shirasugi, M. Chem. Eur. J. 2012, 18, 11219.
  (b) Imae, K.; Shimizu, K.; Ogata, K.; Fukuzawa, S. J. Org. Chem. 2011, 76, 3604.
  (c) Shang, D. J.; Liu, Y. L.; Zhou, X.; Liu, X. H.; Feng, X. M. Chem. Eur. J. 2009, 15, 3678.
  (d) Liang, G.; Tong, M.-C.; Tao, H. Y.; Wang, C.-J. Adv. Synth. Catal. 2010, 352, 1851.
22. [22]
  (a) Hernández-Toribio, J.; Arrayás, R. G.; Carretero, J. C. J. Am. Chem. Soc. 2008, 130, 16150.
  (b) Hernández-Toribio, J.; Arrayás, R. G.; Carretero, J. C. Chem. Eur. J. 2010, 16, 1153.
23. [23]
  (a) Paradisi, M. P.; Torrini, I.; Zecchini, G. P.; Lucente, G.; Gavuzzo, E.; Mazza, F.; Pochetti, G. Tetrahedron 1995, 51, 2379.
  (b) Burgess, K.; Ho, K.-K.; Pal, B. J. Am. Chem. Soc. 1995, 117, 3808.
  (c) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. 1993, 32, 1244.
  (d) Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845.
24. [24]
  (a) You, S.-L.; Hou, X.-L.; Dai, L.-X.; Cao, B.-X.; Sun, J. Chem. Commun. 2000, 1933.
  (b) Kazmaier, U.; Zumpe, F. L. Angew. Chem., Int. Ed. 1999, 38, 1468.
  (c) Trost, B. M.; Ariza, X. J. Am. Chem. Soc. 1999, 121, 10727.
  (d) Kazmaier, U.; Maier, S.; Zumpe, F. L. Synlett 2000, 1523.
  (e) Genet, J. P.; Juge, S.; Achi, S.; Mallart, S.; Ruiz Montes, J.; Levif, G. Tetrahedron 1988, 44, 5263.
  (f) Baldwin, I. C.; Williams, J. M. J.; Beckett, R. P. Tetrahedron: Asymmetry 1995, 6, 1515.
25. [25]
  (a) Cheng, G.; Deng, Y.; Gong, L.; Mi, A.; Cui, X.; Jiang, Y.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron: Asymmetry 2001, 12, 1567.
  (b) Kanayama, T.; Yoshida, K.; Miyabe, H.; Takemoto, Y. Angew. Chem., Int. Ed. 2003, 42, 2054.
  (c) Kanayama, T.; Yoshida, K.; Miyabe, H.; Kimachi, T.; Takemoto, Y. J. Org. Chem. 2003, 68, 6197.
26. [26]
  (a) Malleron, J. L.; Fiaud, J. C.; Legros, J. Y. Handbook of Palladium-Catalyzed Organic Reactions, Academic Press, San Diego, 1997.
  (b) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
  (c) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
  (d) Williams, J. M. J. Synlett 1996, 705.
  (e) Tsuji, J. Palladium Reagents and Catalysts, Wiley, Chichester, 1995.
27. [27]
  (a) Allen, A. E.; MacMillan, D. W. C. Chem. Sci. 2012, 3, 633.
  (b) Du, Z.; Shao, Z. Chem. Soc. Rev. 2013, 42, 1337.
  (c) Butt, N. A.; Zhang, W. Chem. Soc. Rev. 2015, 44, 7929.
  (d) Inamdar, S. M.; Shinde, V. S.; Patil, N. T. Org. Biomol. Chem. 2015, 13, 8116.
28. [28]
  Huo, X.; He, R.; Fu, J.; Zhang, J.; Yang, G.; Zhang, W. J. Am. Chem. Soc. 2017, 139, 9819. doi: 10.1021/jacs.7b05460
29. [29]
  Wei, L.; Xu, S.-M.; Zhu, Q.; Che, C.; Wang, C.-J. Angew. Chem., Int. Ed. 2017, 56, 12312. doi: 10.1002/anie.201707019
30. [30]
  Dolbeare, K.; Pontoriero, G. F.; Gupta, S. K.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 2003, 46, 727. doi: 10.1021/jm020441o
31. [31]
  Wei, L.; Xiao, L.; Wang, C.-J. Adv. Synth. Catal. 201, 360, 4715.
32. [32]
  (a) Huo, X.; Fu, J.; He, X.; Chen, J.; Xie, F.; Zhang, W. Chem. Commun. 2018, 54, 599.
  (b) Liu, P.; Hou, X.; Li, B.; He, R.; Zhang, J.; Wang, T.; Xie, F.; Zhang, W. Org. Lett., 2018, 20, 6564.
33. [33]
  (a) Paradisi, M. P.; Torrini, I.; Zecchini, G. P.; Lucente, G.; Gavuzzo, E.; Mazza, F.; Pochetti, G. Tetrahedron 1995, 51, 2379.
  (b) Burgess, K.; Ho, K.-K.; Pal, B. J. Am. Chem. Soc. 1995, 117, 3808.
  (c) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. 1993, 32, 1244.
  (d) Balaram, P. Curr. Opin. Struct. Biol. 1992, 2, 845.
34. [34]
  Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis, Vol. Ⅰ~Ⅲ, Suppl. Ⅰ~Ⅱ, Springer, New York, 1999.
35. [35]
  Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. doi: 10.1021/cr00020a002
36. [36]
  (a) Luparia, M.; Oliveira, M. T.; Audisio, D.; Frébault, F.; Goddard, R.; Maulide, N. Angew. Chem., Int. Ed. 2011, 50, 12631.
  (b) McInturff, E. L.; Yamaguchi, E.; Krische, M. J. J. Am. Soc. Chem. 2012, 134, 20628.
  (c) Morgen, M.; Bretzke, S.; Li, P.; Menche, D. Org. Lett. 2010, 12, 4494.
  (d) Nojiri, A.; Kumagai, N.; Shibasaki, M. J. Am. Soc. Chem. 2009, 131, 3779.
  (e) Tian, X.; Cassani, C.; Liu, Y.; Moran, A.; Urakawa, A.; Galzerano, P.; Arceo, E.; Melchiorre, P. J. Am. Soc. Chem. 2011, 133, 17934.
  (f) Wang, B.; Wu, F.; Wang, Y.; Liu, X.; Deng, L. J. Am. Soc. Chem. 2007, 129, 768.
37. [37]
  (a) Krautwald, S.; Sarlah, D.; Schafroth, M. A.; Carreira, E. M. Science 2013, 340, 1065.
  (b) Krautwald, S.; Sarlah, D.; Schafroth, M. A.; Carreira, E. M. J. Am. Chem. Soc. 2014, 136, 3020.
  (c) Sandmeier, T.; Krautwald, S.; Zipfel, H. F.; Carreira, E. M. Angew. Chem., Int. Ed. 2015, 54, 14363.
38. [38]
  (a) Nӕsborg, L.; Halskov, K. S.; Tur, F.; Mønsted, S. M. N.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2015, 54, 10193.
  (b); Huo, X.; He, R.; Zhang, X.; Zhang, W. J. Am. Chem. Soc. 2016, 138, 11093.
  (c) Cruz, F. A.; Dong, V. M. J. Am. Chem. Soc. 2017, 139, 1029.
  (d) Jiang, X.; Beiger, J. J.; Hartwig, J. F. J. Am. Chem. Soc. 2017, 139, 87.
  (f) Zheng, H.; Wang, Y.; Xu, C.; Xu, X.; Lin, L.; Liu, X.; Feng, X. Nat. Commun. 2018, 9, 1968.
39. [39]
  Wei, L.; Zhu, Q.; Xu, S.-M.; Chang, X.; Wang, C.-J. J. Am. Chem. Soc. 2018, 140, 1508. doi: 10.1021/jacs.7b12174
40. [40]
  Kiener, C. A.; Shu, C.; Incarvito, C.; Hartwig, J. H. J. Am. Chem. Soc. 2003, 125, 14272. doi: 10.1021/ja038319h
41. [41]
  (a) Raskatov, J. A.; Spiess, S.; Gnamm, C.; Brö dner, K.; Rominger, F.; Helmchen, G. Chem. Eur. J. 2010, 16, 6601.
  (b) Spiess, S.; Welter, C.; Franck, G.; Taquet, J.-P.; Helmchen, G. Angew. Chem., Int. Ed. 2008, 47, 7652.
42. [42]
  (a) Wu, A.; Chakraborty, A.; Fettinger, J. C.; Flowers Ii, R. A.; Isaacs, L. Angew. Chem., Int. Ed. 2002, 41, 4028.
  (b) Safont-Sempere, M. M.; Fernández, G.; Würthner, F. Chem. Rev. 2011, 111, 5784.
  (c) He, Z.; Jiang, W.; Schalley, C. A. Chem. Soc. Rev. 2015, 44, 779.
43. [43]
  (a) Morimoto, Y.; Takaishi, M.; Kinoshita, T.; Sakaguchi, K.; Shibata, K. Chem. Commun. 2002, 42.
  (b) Spangenberg, T.; Schoenfelder, A.; Breit, B.; Mann, A. Org. Lett. 2007, 9, 3881.
44. [44]
  Huo, X.; Zhang, J.; Fu, J.; He, R.; Zhang, W. J. Am. Chem. Soc. 2018, 140, 2080. doi: 10.1021/jacs.8b00187
45. [45]
  (a) Nugent, T. C. Chiral Amine Synthesis: Methods, Developments and Applications, Wiley-VCH, Weinheim, 2010.
  (b) Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595.
  (c) Przheval'skii, N. M.; Grandberg, I. I. Usp. Khim. 1987, 56, 814.
  (d) Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. Chem. Rev. 2011, 111, 2626.
  (e) Yus, M.; González-Gómez, J. C.; Foubelo, F. Chem. Rev. 2011, 111, 7774.
  (f) Yus, M.; González-Gómez, J. C.; Foubelo, F. Chem. Rev. 2013, 113, 5595.
46. [46]
  Wei, L.; Zhu, Q.; Xiao, L.; Tao, H.-Y.; Wang, C.-J. Nat. Commun. 2019, 10, 1594. doi: 10.1038/s41467-019-09563-6
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
5. [5]
  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
6. [6]
  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
7. [7]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
8. [8]
  Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO₂ mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398
9. [9]
  Hong CAI , Jiewen WU , Jingyun LI , Lixian CHEN , Siqi XIAO , Dan LI . Synthesis of a zinc-cobalt bimetallic adenine metal-organic framework for the recognition of sulfur-containing amino acids. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 114-122. doi: 10.11862/CJIC.20240382
10. [10]
  Jingzhao Cheng , Shiyu Gao , Bei Cheng , Kai Yang , Wang Wang , Shaowen Cao . 4-氨基-1H-咪唑-5-甲腈修饰供体-受体型氮化碳光催化剂的构建及其高效光催化产氢研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406026-. doi: 10.3866/PKU.WHXB202406026
11. [11]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
12. [12]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
13. [13]
  Honghong Zhang , Zhen Wei , Derek Hao , Lin Jing , Yuxi Liu , Hongxing Dai , Weiqin Wei , Jiguang Deng . Recent advances in synergistic catalytic valorization of CO₂ and hydrocarbons by heterogeneous catalysis. Acta Physico-Chimica Sinica, 2025, 41(7): 100073-. doi: 10.1016/j.actphy.2025.100073
14. [14]
  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
15. [15]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . 杂多酸H₃PW₁₂O₄₀高效催化MgH₂储氢. Acta Physico-Chimica Sinica, 2025, 41(1): 2308032-. doi: 10.3866/PKU.WHXB202308032
16. [16]
  Tao Cao , Fang Fang , Nianguang Li , Yinan Zhang , Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
17. [17]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
18. [18]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
19. [19]
  Yi Yang , Xin Zhou , Miaoli Gu , Bei Cheng , Zhen Wu , Jianjun Zhang . Femtosecond transient absorption spectroscopy investigation on ultrafast electron transfer in S-scheme ZnO/CdIn₂S₄ photocatalyst for H₂O₂ production and benzylamine oxidation. Acta Physico-Chimica Sinica, 2025, 41(6): 100064-. doi: 10.1016/j.actphy.2025.100064
20. [20]
  Qiuyu Xiang , Chunhua Qu , Guang Xu , Yafei Yang , Yue Xia . A Journey beyond “Alum”. University Chemistry, 2024, 39(11): 189-195. doi: 10.12461/PKU.DXHX202404094

Get Citation

PDF

XML

Metrics

PDF Downloads(43)
Abstract views(1863)
HTML views(414)

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