Citation: Liang Tingting, Jiang Lan, Gan Miaomiao, Su Xin, Li Zhengning. Domino Reactions Initialized by Copper-Catalyzed Hydrocupration of C-C Unsaturated Bonds[J]. Chinese Journal of Organic Chemistry, ;2017, 37(12): 3096-3111. doi: 10.6023/cjoc201706004 shu

Domino Reactions Initialized by Copper-Catalyzed Hydrocupration of C-C Unsaturated Bonds

College of Environmental and Chemical Engineering, Dalian University, Dalian 116622

Corresponding author: Li Zhengning, lizhengning@dlu.edu.cn
Received Date: 2 June 2017
Revised Date: 4 July 2017
Available Online: 16 December 2017
Fund Project: the Natural Science Foundation of Liaoning Province 2015020678Project supported by the Natural Science Foundation of Liaoning Province (No. 2015020678)

Figures(23)

Compared with sequential reactions, domino reactions are more efficient and highly desirable in organic synthesis as fewer operational and purification procedures are involved, yielding the product with complexity in a more economic and environmently friendly manner. Domino reactions induced by copper-catalyzed hydrocupration of unsaturated C-C bonds in α, β-unsaturated ketones, α, β-unsaturated carboxylates, aryl alkenes, aliphatic alkenes and even alkynes are reviewed. A hydrosilane is used as a hydride source for CuH formation and the hydrocupration intermediates undergo subsequent addition to polar unsaturated bonds, e.g. carbonyls and imines, or proceed to substitution reactions, and finally, reaction involving two or more newly formed bonds proceed without purification of intermediate products or changing the operational conditions. Because of its simplicity and efficiency, this method is highly valuable in organic synthesis.
- domino reaction,
- catalysis,
- copper,
- hydrocupration,
- reduction,
- alkene
1. [1]
  Tietze, L. F. Chem. Rev. 1996, 96, 115. doi: 10.1021/cr950027e
2. [2]
  Pellissier, H. Chem. Rev. 2013, 113, 442. doi: 10.1021/cr300271k
3. [3]
  Saebang, Y.; Rukachaisirikul, V.; Kaeobamrung, J. Tetrahedron Lett. 2017, 58, 168. doi: 10.1016/j.tetlet.2016.12.006
4. [4]
  Pellissier, H. Adv. Synth. Catal. 2015, 357, 2745. doi: 10.1002/adsc.v357.13
5. [5]
  Li, X.-W.; Wang, C.-Y.; Zheng, L.-Y. Chin. J. Org. Chem. 2006, 26, 1144(in Chinese). doi: 10.3321/j.issn:0253-2786.2006.08.024
6. [6]
  Chen, J.; Liu, Q.; Dai, X.-Y.; Nie, L.-L.; Fang, H.-H.; Wu, X.-Y. Chin. J. Org. Chem. 2013, 33, 1(in Chinese).
7. [7]
  Zhu, H.; Ye, C.-Q.; Chen, Z.-Y. Chin. J. Org. Chem. 2015, 35, 2291(in Chinese).
8. [8]
  Feng, Y.-D.; Zhang, H.; Cheng, G.-L.; Cui, X.-L. Chin. J. Org. Chem. 2014, 34, 1499(in Chinese).
9. [9]
  Zhang, W.; Wang, Y.; Bai, C.; Wen, J.; Wang, N. Chin. J. Chem. 2015, 33, 401. doi: 10.1002/cjoc.v33.4
10. [10]
  Schmid, T. E.; Drissi-Amraoui, S.; Crévisy, C.; Baslé, O.; Mauduit, M. Beilstein J. Org. Chem. 2015, 11, 2418. doi: 10.3762/bjoc.11.263
11. [11]
  Phelan, J. P.; Ellman, J. A. Beilstein J. Org. Chem. 2016, 12, 1203. doi: 10.3762/bjoc.12.116
12. [12]
  Yu, Y. F.; San, F.-J.; Li, Z.-N.; Jiang, L. Chin. J. Org. Chem. 2011, 31, 443(in Chinese).
13. [13]
  Tang, F.-X.; Ye, J.-Y. Chin. J. Org. Chem. 2015, 35, 1414(in Chinese).
14. [14]
  Mori, A.; Fujita, A.; Nishihara, Y.; Hiyama, T. Chem. Commun. 1997, 2159.
15. [15]
  Jordan, A. J.; Lalic, G.; Sadighi, J. P. Chem. Rev. 2016, 116, 8318. doi: 10.1021/acs.chemrev.6b00366
16. [16]
  Fang, Q.; Sui, Y.-Z.; Yu, J.-L.; Xie, L.-J.; Yaag, L.-Y.; Wu, J.-W.; Wu, J. J. Hangzhou Normal Univ. (Nat. Sci. Ed.) 2015, 14, 1(in Chinese). doi: 10.3969/j.issn.1674-232X.2015.01.001
17. [17]
  Galestokova, Z.; Sebesta, R. Eur. J. Org. Chem. 2012, 6688.
18. [18]
  Pellissier, H. Adv. Synth. Catal. 2016, 358, 2194. doi: 10.1002/adsc.v358.14
19. [19]
  Li, Z.; Liu, G.; Pauline, C. Prog. Chem. 2008, 20, 1909.
20. [20]
  Lipshutz, B. H. Synlett 2009, 509.
21. [21]
  Deutsch, C.; Krause, N.; Lipshutz, B. H. Chem. Rev. 2008, 108, 2916. doi: 10.1021/cr0684321
22. [22]
  Rendler, S.; Oestreich, M. Angew. Chem., Int. Ed. 2007, 46, 498. doi: 10.1002/(ISSN)1521-3773
23. [23]
  Chiu, P. Synthesis-Stuttgart 2004, 2210.
24. [24]
  Nishiyama, H.; Shiomi, T. In Metal Catalyzed Reductive C-C Bond Formation:A Departure from Preformed Organometallic Reagents, Ed.:Krische, M. J., Springer Berlin Heidelberg, Berlin, Heidelberg, 2007, p. 105.
25. [25]
  Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809. doi: 10.1016/S0040-4039(00)96631-0
26. [26]
  Chiu, P.; Leung, S. K. Chem. Commun. 2004, 2308.
27. [27]
  Lam, H. W.; Joensuu, P. M. Org. Lett. 2005, 7, 4225. doi: 10.1021/ol051649h
28. [28]
  Zheng, A.; Jiang, L.; Li, Z. Chin. J. Chem. 2012, 30, 2587. doi: 10.1002/cjoc.201200523
29. [29]
  Lam, H. W.; Murray, G. J.; Firth, J. D. Org. Lett. 2005, 7, 5743. doi: 10.1021/ol052599j
30. [30]
  Lipshutz, B. H.; Amorelli, B.; Unger, J. B. J. Am. Chem. Soc. 2008, 130, 14378. doi: 10.1021/ja8045475
31. [31]
  Deschamp, J.; Riant, O. Org. Lett. 2009, 11, 1217. doi: 10.1021/ol802879f
32. [32]
  Ou, J.; Wong, W. T.; Chiu, P. Org. Biomol. Chem. 2012, 10, 5971. doi: 10.1039/c2ob25206f
33. [33]
  Zhao, D.; Oisaki, K.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2006, 47, 1403. doi: 10.1016/j.tetlet.2005.12.097
34. [34]
  Li, Z.; Jiang, L.; Li, Z.; Chen, H. Chin. J. Chem. 2013, 31, 539. doi: 10.1002/cjoc.201300036
35. [35]
  Zhao, D.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 14440. doi: 10.1021/ja0652565
36. [36]
  Deschamp, J.; Chuzel, O.; Hannedouche, J.; Riant, O. Angew. Chem., Int. Ed. 2006, 45, 1292. doi: 10.1002/(ISSN)1521-3773
37. [37]
  Kato, M.; Oki, H.; Ogata, K.; Fukuzawa, S.-I. Synlett 2009, 1299.
38. [38]
  Chuzel, O.; Deschamp, J.; Chausteur, C.; Riant, O. Org. Lett. 2006, 8, 5943. doi: 10.1021/ol062398v
39. [39]
  Welle, A.; Diez-Gonzalez, S.; Tinant, B.; Nolan, S. P.; Riant, O. Org. Lett. 2006, 8, 6059. doi: 10.1021/ol062495o
40. [40]
  Li, Z.; Zhang, Z.; Yuan, L.; Jiang, L.; Li, Z.; Li, Z. Synlett 2014, 25, 724. doi: 10.1055/s-00000083
41. [41]
  Li, R.; Li, Z.; Jiang, L.; Li, Z. Chem. Pap. 2017, 71, 1825. doi: 10.1007/s11696-017-0175-y
42. [42]
  Li, Z.; Li, R.; Gan, M.; Jiang, L.; Li, Z. Tetrahedron Lett. 2015, 56, 5541. doi: 10.1016/j.tetlet.2015.08.031
43. [43]
  Yang, T.; Zhang, Y.; Cao, P.; Wang, M.; Li, L.; Li, D.; Liao, J. Tetrahedron 2016, 72, 2707. doi: 10.1016/j.tet.2015.12.062
44. [44]
  Li, Z.; Wang, C.; Li, Z. Beilstein J. Org. Chem. 2015, 11, 213. doi: 10.3762/bjoc.11.23
45. [45]
  Du, Y.; Xu, L.-W.; Shimizu, Y.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 16146. doi: 10.1021/ja8069727
46. [46]
  Suto, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 500. doi: 10.1021/ja068226a
47. [47]
  Li, Z.; Feng, Y.; Li, Z.; Jiang, L. Synlett 2014, 25, 2899. doi: 10.1055/s-00000083
48. [48]
  Oswald, C. L.; Peterson, J. A.; Lam, H. W. Org. Lett. 2009, 11, 4504. doi: 10.1021/ol901560r
49. [49]
  Li, Z.; Li, R.; Jiang, L.; Li, Z. Molecules 2015, 20, 15023. doi: 10.3390/molecules200815023
50. [50]
  Miller, S. P.; Morken, J. P. Org. Lett. 2002, 4, 2743. doi: 10.1021/ol026273b
51. [51]
  Wong, K. C.; Ng, E.; Wong, W. T.; Chiu, P. Chem. Eur. J. 2016, 22, 3709. doi: 10.1002/chem.201504870
52. [52]
  Linstadt, R. T. H.; Peterson, C. A.; Jette, C. I.; Boskovic, Z. V.; Lipshutz, B. H. Org. Lett. 2017, 19, 328. doi: 10.1021/acs.orglett.6b03464
53. [53]
  Reznichenko, A. L.; Nawara-Hultzsch, A. J.; Hultzsch, K. C. In Stereoselective Formation of Amines, Eds.:Li, W.; Zhang, X., Springer Berlin Heidelberg, Berlin, Heidelberg, 2014, p. 191.
54. [54]
  Huang, L.; Arndt, M.; Gooßen, K.; Heydt, H.; Gooßen, L. J. Chem. Rev. 2015, 115, 2596. doi: 10.1021/cr300389u
55. [55]
  Murphy, S. K.; Dong, V. M. Chem. Commun. 2014, 50, 13645. doi: 10.1039/C4CC02276A
56. [56]
  Rupnicki, L.; Saxena, A.; Lam, H. W. J. Am. Chem. Soc. 2009, 131, 10386. doi: 10.1021/ja904365h
57. [57]
  Soradova, Z.; Sebesta, R. ChemCatChem 2016, 8, 2581. doi: 10.1002/cctc.201600252
58. [58]
  Pirnot, M. T.; Wang, Y. M.; Buchwald, S. L. Angew. Chem., Int. Ed. 2016, 55, 48. doi: 10.1002/anie.201507594
59. [59]
  Gribble, M. W.; Pirnot, M. T.; Bandar, J. S.; Liu, R. Y.; Buchwald, S. L. J. Am. Chem. Soc. 2017, 139, 2192. doi: 10.1021/jacs.6b13029
60. [60]
  Saxena, A.; Choi, B.; Lam, H. W. J. Am. Chem. Soc. 2012, 134, 8428. doi: 10.1021/ja3036916
61. [61]
  Yang, Y.; Perry, I. B.; Lu, G.; Liu, P.; Buchwald, S. L. Science 2016, 353, 144. doi: 10.1126/science.aaf7720
62. [62]
  Choi, B.; Saxenaa, A.; Smith, J. J.; Churchill, G. H.; Lam, H. W. Synlett 2015, 26, 350.
63. [63]
  Ascic, E.; Buchwald, S. L. J. Am. Chem. Soc. 2015, 137, 4666. doi: 10.1021/jacs.5b02316
64. [64]
  Yang, Y.; Perry, I. B.; Buchwald, S. L. J. Am. Chem. Soc. 2016, 138, 9787. doi: 10.1021/jacs.6b06299
65. [65]
  Liu, R. Y.; Yang, Y.; Buchwald, S. L. Angew. Chem., Int. Ed. 2016, 55, 14077. doi: 10.1002/anie.v55.45
66. [66]
  Kokubo, K.; Miura, M.; Nomura, M. Organometallics 1995, 14, 4521. doi: 10.1021/om00010a016
67. [67]
  Hong, Y.-T.; Barchuk, A.; Krische, M. J. Angew. Chem., Int. Ed. 2006, 45, 6885. doi: 10.1002/(ISSN)1521-3773
68. [68]
  Fujihara, T.; Tatsumi, K.; Terao, J.; Tsuji, Y. Org. Lett. 2013, 15, 2286. doi: 10.1021/ol400862k
69. [69]
  Bandar, J. S.; Ascic, E.; Buchwald, S. L. J. Am. Chem. Soc. 2016, 138, 5821. doi: 10.1021/jacs.6b03086
70. [70]
  Sato, K.; Isoda, M.; Ohata, S.; Morita, S.; Tarui, A.; Omote, M.; Kumadaki, I.; Ando, A. Adv. Synth. Catal. 2012, 354, 510. doi: 10.1002/adsc.v354.2/3
71. [71]
  Miki, Y.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2013, 52, 10830. doi: 10.1002/anie.201304365
72. [72]
  Miki, Y.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2014, 16, 1498. doi: 10.1021/ol5003219
73. [73]
  Zhu, S.; Niljianskul, N.; Buchwald, S. L. J. Am. Chem. Soc. 2013, 135, 15746. doi: 10.1021/ja4092819
74. [74]
  Zhu, S.; Buchwald, S. L. J. Am. Chem. Soc. 2014, 136, 15913. doi: 10.1021/ja509786v
75. [75]
  Niu, D.; Buchwald, S. L. J. Am. Chem. Soc. 2015, 137, 9716. doi: 10.1021/jacs.5b05446
76. [76]
  Niljianskul, N.; Zhu, S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2015, 54, 1638. doi: 10.1002/anie.201410326
77. [77]
  Yang, Y.; Shi, S. L.; Niu, D. W.; Liu, P.; Buchwald, S. L. Science 2015, 349, 62. doi: 10.1126/science.aab3753
78. [78]
  Xi, Y.; Butcher, T. W.; Zhang, J.; Hartwig, J. F. Angew. Chem., Int. Ed. 2016, 55, 776. doi: 10.1002/anie.201509235
79. [79]
  Zhu, S. L.; Niljianskul, N.; Buchwald, S. L. Nat. Chem. 2016, 8, 144. doi: 10.1038/nchem.2418
80. [80]
  Moser, R.; Boskovic, Z. V.; Crowe, C. S.; Lipshutz, B. H. J. Am. Chem. Soc. 2010, 132, 7852. doi: 10.1021/ja102689e
81. [81]
  Mohr, J.; Oestreich, M. Angew. Chem., Int. Ed. 2016, 55, 12148. doi: 10.1002/anie.201606701
82. [82]
  Shi, S.-L.; Wong, Z. L.; Buchwald, S. L. Nature 2016, 532, 353. doi: 10.1038/nature17191
83. [83]
  Shi, S. L.; Buchwald, S. L. Nat. Chem. 2015, 7, 38. doi: 10.1038/nchem.2131
84. [84]
  Nishikawa, D.; Sakae, R.; Miki, Y.; Hirano, K.; Miura, M. J. Org. Chem. 2016, 81, 12128. doi: 10.1021/acs.joc.6b02483
85. [85]
  Wang, Y.-M.; Bruno, N. C.; Placeres, A. L.; Zhu, S.; Buchwald, S. L. J. Am. Chem. Soc. 2015, 137, 10524. doi: 10.1021/jacs.5b07061
86. [86]
  Semba, K.; Ariyama, K.; Zheng, H.; Kameyama, R.; Sakaki, S.; Nakao, Y. Angew. Chem., Int. Ed. 2016, 55, 6275. doi: 10.1002/anie.201511975
87. [87]
  Friis, S. D.; Pirnot, M. T.; Buchwald, S. L. J. Am. Chem. Soc. 2016, 138, 8372. doi: 10.1021/jacs.6b04566
88. [88]
  Wang, Y.-M.; Buchwald, S. L. J. Am. Chem. Soc. 2016, 138, 5024. doi: 10.1021/jacs.6b02527
89. [89]
  Lee, J.; Torker, S.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2017, 56, 821. doi: 10.1002/anie.201611444
90. [90]
  Uehling, M. R.; Suess, A. M.; Lalic, G. J. Am. Chem. Soc. 2015, 137, 1424. doi: 10.1021/ja5124368
91. [91]
  Suess, A. M.; Uehling, M. R.; Kaminsky, W.; Lalic, G. J. Am. Chem. Soc. 2015, 137, 7747. doi: 10.1021/jacs.5b03086
1. [1]
  Xudong Lv , Tao Shao , Junyan Liu , Meng Ye , Shengwei Liu . Paired Electrochemical CO₂ Reduction and HCHO Oxidation for the Cost-Effective Production of Value-Added Chemicals. Acta Physico-Chimica Sinica, 2024, 40(5): 2305028-0. doi: 10.3866/PKU.WHXB202305028
2. [2]
  Zhenxing Liu , Jiaen Hu , Zishi Cheng , Xinqi Hao . 基础有机化学教学中烯烃的氧化反应. University Chemistry, 2025, 40(6): 139-144. doi: 10.12461/PKU.DXHX202408107
3. [3]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
4. [4]
  Qi Zhang , Ziyu Liu , Hongxia Tan , Jun Tong , Dazhen Xu . Research Progress on Direct Synthesis of β-Hydroxy Sulfones via Difunctionalization of Olefins. University Chemistry, 2025, 40(11): 199-209. doi: 10.12461/PKU.DXHX202412064
5. [5]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
6. [6]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . Catalytic Effect of H₃PW₁₂O₄₀ on Hydrogen Storage of MgH₂. Acta Physico-Chimica Sinica, 2025, 41(1): 100001-0. doi: 10.3866/PKU.WHXB202308032
7. [7]
  Xiaogang Liu , Mengyu Chen , Yanyan Li , Xiantao Ma . Experimental Reform in Applied Chemistry for Cultivating Innovative Competence: A Case Study of Catalytic Hydrogen Production from Liquid Formaldehyde Reforming at Room Temperature. University Chemistry, 2025, 40(7): 300-307. doi: 10.12461/PKU.DXHX202408007
8. [8]
  Wenjuan SHI , Yuke LU , Xiuyuan LI , Lei HOU , Yaoyu WANG . Mg(Ⅱ) metal-organic frameworks based on biphenyltetracarboxylic acid: Synthesis and CO₂ adsorption and catalytic conversion performance. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2455-2463. doi: 10.11862/CJIC.20250220
9. [9]
  Weihan Zhang , Menglu Wang , Ankang Jia , Wei Deng , Shuxing Bai . Surface Sulfur Species Influence Hydrogenation Performance of Palladium-Sulfur Nanosheets. Acta Physico-Chimica Sinica, 2024, 40(11): 2309043-0. doi: 10.3866/PKU.WHXB202309043
10. [10]
  Yongxin LIU , Xingchen LI , Hongjia LIU , Danni LI , Tao ZHANG , Xi CHEN . Enhancement effect of Fe₃O₄ conversion to MIL-100(Fe) on activation of persulfate for degradation of antibiotic. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2503-2513. doi: 10.11862/CJIC.20250169
11. [11]
  Jiapei Zou , Junyang Zhang , Xuming Wu , Cong Wei , Simin Fang , Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081
12. [12]
  Haoyu Sun , Dun Li , Yuanyuan Min , Yingying Wang , Yanyun Ma , Yiqun Zheng , Hongwen Huang . Hierarchical Palladium-Copper-Silver Porous Nanoflowers as Efficient Electrocatalysts for CO₂ Reduction to C₂₊ Products. Acta Physico-Chimica Sinica, 2024, 40(6): 2307007-0. doi: 10.3866/PKU.WHXB202307007
13. [13]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
14. [14]
  Pengzi Wang , Wenjing Xiao , Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090
15. [15]
  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
16. [16]
  Haotong Ma , Mingyu Heng , Yang Xu , Wei Bi , Yingchun Miao , Shuning Xiao . Synergistic carbon doping and Cu loading on boron nitride via microwave synthesis for enhanced atmospheric CO₂ photoreduction. Acta Physico-Chimica Sinica, 2025, 41(11): 100132-0. doi: 10.1016/j.actphy.2025.100132
17. [17]
  Xue Dong , Xiaofu Sun , Shuaiqiang Jia , Shitao Han , Dawei Zhou , Ting Yao , Min Wang , Minghui Fang , Haihong Wu , Buxing Han . Electrochemical CO₂ Reduction to C₂₊ Products with Ampere-Level Current on Carbon-Modified Copper Catalysts. Acta Physico-Chimica Sinica, 2025, 41(3): 100024-0. doi: 10.3866/PKU.WHXB202404012
18. [18]
  Dong Xiang , Kunzhen Li , Kanghua Miao , Ran Long , Yujie Xiong , Xiongwu Kang . Amine-Functionalized Copper Catalysts: Hydrogen Bonding Mediated Electrochemical CO₂ Reduction to C₂ Products and Superior Rechargeable Zn-CO₂ Battery Performance. Acta Physico-Chimica Sinica, 2024, 40(8): 2308027-0. doi: 10.3866/PKU.WHXB202308027
19. [19]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
20. [20]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317

Get Citation

PDF

XML

Metrics

PDF Downloads(46)
Abstract views(4503)
HTML views(944)

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