Citation: HU Yuanyuan, WANG Congyang. Bimetallic C―H Activation in Homogeneous Catalysis[J]. Acta Physico-Chimica Sinica, ;2019, 35(9): 913-922. doi: 10.3866/PKU.WHXB201809036 shu

Bimetallic C―H Activation in Homogeneous Catalysis

HU Yuanyuan ^1,2 ,
WANG Congyang ^1,2,,

1.
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China
2.
University of Chinese Academy of Sciences, Beijing 100049, P. R. China

Author Bio:
WANG Congyang obtained his B.S. degree from Nanjing University in 2000 and his Ph.D. degree from Peking University under the guidance of Prof. Zhenfeng Xi in 2005. After a postdoctoral stay in the same group, he moved to the University of Münster, Germany, working with Prof. Frank Glorius as an Alexander von Humboldt Research Fellow. In 2010, he started his independent research career at Institute of Chemistry, Chinese Academy of Sciences as a professor. In 2015, he became a joint professor at the University of Chinese Academy of Sciences (UCAS). Currently, his research interest focuses on manganese-group-metal catalysis
Corresponding author: WANG Congyang, wangcy@iccas.ac.cn
Received Date: 21 September 2018
Revised Date: 25 October 2018
Accepted Date: 25 October 2018
Available Online: 29 September 2018
Fund Project: The project was supported by the National Natural Science Foundation of China 21521002The project was supported by the National Natural Science Foundation of China (21472194, 21772202, 21521002)The project was supported by the National Natural Science Foundation of China 21772202The project was supported by the National Natural Science Foundation of China 21472194

The strategy of transition-metal-catalyzed C―H activation has been greatly developed in recent years. Direct transformations of inert C―H bonds undoubtedly provide powerful ways to construct various C―C and C―X (X = heteroatom) bonds, with enhanced atom- and step-economy. Impressive efforts have been devoted to this research all along. However, concerns about reactivity and selectivity remain to be tackled, due to their strong dependence on directing groups and acidic reactive sites. In this regard, more effective catalytic systems are of great importance and therefore in high demand. Bimetallic C―H activation, by virtue of the cooperative effect, has emerged as a promising solution to this issue. The intriguing interactions between two metals with substrates afford exceptional reaction efficiency and selectivity. Intensive interest in both experimental and computational studies has been recently triggered. In this minireview, diverse bimetallic catalytic reactions are summarized into three categories according to the initiator in the C―H activation step, namely, bimetallic catalyses based on palladium, nickel, and other metals. Experimental results as well as density functional theory (DFT) calculations are invoked in the plausible mechanistic considerations. In the first part, collaborative modes based on palladium are described, in which magnesium, chromium, cobalt, and silver are successfully engaged as accessory partners. Most of them stabilize the C―H activation transition states by decreasing the energy, thus facilitating the cleavage of C―H bonds. Notably, some reactions previously reported as examples of monomeric palladium catalysis are now reinvestigated as bimetallic scenarios, in light of computational discussions. In the second part, reactions based on the synergy of nickel, and zinc or aluminum, are generalized, in which zinc or aluminum acts as a Lewis acid to increase the acidity of C―H bonds. It has been shown that the choice of different kinds of Lewis acids and ligands has a great influence on the reaction chemo-, regio-, and stereoselectivity. Gratefully, even enantioselective transformations can be achieved using the cooperation of nickel and aluminum. Moreover, a key reaction intermediate in the bimetallic C―H activation by nickel and aluminum has been isolated, providing guidance for this bimetallic catalytic system in further mechanistic studies and applications. In the last part, synergetic catalysis based on various other metals is presented. Bimetallic regimes of ruthenium/copper, rhodium/bismuth, iridium/aluminum, manganese/zinc, and zirconium/aluminum have been elegantly applied to C―H activation reactions. Multifarious action modes are proposed on account of the mechanistic research.
- Bimetallic synergy,
- C―H activation,
- Reaction mechanism,
- Homogeneous catalysis,
- Organic synthesis
1. [1]
  Yu, J. Q.; Shi, Z. -J. C―H Activation; Springer: Berlin, Germany, 2010.
2. [2]
  Li, C. -J. Acc. Chem. Res. 2009, 42, 335. doi: 10.1021/ar800164n doi: 10.1021/ar800164n
3. [3]
  Sun, C. -L.; Li, B. -J.; Shi, Z. -J. Chem. Rev. 2011, 111, 1293. doi: 10.1021/cr100198w doi: 10.1021/cr100198w
4. [4]
  Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879. doi: 10.1021/cr300153j doi: 10.1021/cr300153j
5. [5]
  Wencel-Delord, J.; Glorius, F. Nat. Chem. 2013, 5, 369. doi: 10.1038/nchem.1607 doi: 10.1038/nchem.1607
6. [6]
  Song, G.; Li, X. Acc. Chem. Res. 2015, 48, 1007. doi: 10.1021/acs.accounts.5b00077 doi: 10.1021/acs.accounts.5b00077
7. [7]
  Moselage, M.; Li, J.; Ackermann, L. ACS Catal. 2016, 6, 498. doi: 10.1021/acscatal.5b02344 doi: 10.1021/acscatal.5b02344
8. [8]
  He, J.; Wasa, M.; Chan, K. S. L.; Shao, Q.; Yu, J. -Q. Chem. Rev. 2017, 117, 8754. doi: 10.1021/acs.chemrev.6b00622 doi: 10.1021/acs.chemrev.6b00622
9. [9]
  Hummel, J. R.; Boerth, J. A.; Ellman, J. A. Chem. Rev. 2017, 117, 9163. doi: 10.1021/acs.chemrev.6b00661 doi: 10.1021/acs.chemrev.6b00661
10. [10]
  Shang, R.; Ilies, L.; Nakamura, E. Chem. Rev. 2017, 117, 9086. doi: 10.1021/acs.chemrev.6b00772 doi: 10.1021/acs.chemrev.6b00772
11. [11]
  Hu, Y.; Zhou, B.; Wang, C. Acc. Chem. Res. 2018, 51, 816. doi: 10.1021/acs.accounts.8b00028 doi: 10.1021/acs.accounts.8b00028
12. [12]
  de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2004.
13. [13]
  Sinfelt, J. H. Acc. Chem. Res. 1977, 10, 15. doi: 10.1021/ar50109a003 doi: 10.1021/ar50109a003
14. [14]
  Sinfelt, J. H. Bimetallic Catalysis: Discoveries, Concepts and Applications; John Wiley and Sons: New York, USA, 1983.
15. [15]
  Shibasaki, M.; Yamamoto, Y. Multimetallic Catalysts in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2004. doi: 10.1126/science.1135941
16. [16]
  Stamenkovic, V. R.; Fowler, B.; Mun, B. S.; Wang, G. F.; Ross, P. N.; Lucas, C. A.; Markovic, N. M. Science 2007, 315, 493. doi: 10.1126/science.1135941 doi: 10.1039/b608694m
17. [17]
  Wang, C.; Xi, Z. Chem. Soc. Rev. 2007, 36, 1395. doi: 10.1039/b608694m doi: 10.1021/cr500208k
18. [18]
  Buchwalter, P.; Rosé, J.; Braunstein, P. Chem. Rev. 2015, 115, 28. doi: 10.1021/cr500208k doi: 10.1039/c6sc05556g
19. [19]
  Mankad, N. P. Chem. Commun. 2018, 54, 1291. doi: 10.1039/c7cc09675e doi: 10.1039/c7cc09675e
20. [20]
  Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861. doi: 10.1021/cr0200217 doi: 10.1021/cr0200217
21. [21]
  Du Bois, J. Org. Process Res. Dev. 2011, 15, 758. doi: 10.1021/op200046v doi: 10.1021/op200046v
22. [22]
  Kornecki, K. P.; Briones, J. F.; Boyarshikh, V.; Fullilove, F.; Autschbach, J.; Schrote, K. E.; Lancaster, K. M.; Davies, H. M.; Berry, J. F. Science 2013, 342, 351. doi: 10.1126/science.1243200 doi: 10.1126/science.1243200
23. [23]
  Davies, H. M. L.; Morton, D. ACS Cent. Sci. 2017, 3, 936. doi: 10.1021/acscentsci.7b00329 doi: 10.1021/acscentsci.7b00329
24. [24]
  Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147. doi: 10.1021/cr900184e doi: 10.1021/cr900184e
25. [25]
  Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050. doi: 10.1021/ja043273t doi: 10.1021/ja043273t
26. [26]
  Ricci, P.; Kr mer, K.; Cambeiro, X. C.; Larrosa, I. J. Am. Chem. Soc. 2013, 135, 13258. doi: 10.1021/ja405936s doi: 10.1021/ja405936s
27. [27]
  Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215. doi: 10.1021/cr100280d doi: 10.1021/cr100280d
28. [28]
  Ricci, P.; Kr mer, K.; Larrosa, I. J. Am. Chem. Soc. 2014, 136, 18082. doi: 10.1021/ja510260j doi: 10.1021/ja510260j
29. [29]
  Whitaker, D.; Batuecas, M.; Ricci, P.; Larrosa, I. Chem. Eur. J. 2017, 23, 12763. doi: 10.1002/chem.201703527 doi: 10.1002/chem.201703527
30. [30]
  Huang, G. -H.; Li, J. -M.; Huang, J. -J.; Lin, J. -D.; Chuang, G. J. Chem. Eur. J. 2014, 20, 5240. doi: 10.1002/chem.201304633 doi: 10.1002/chem.201304633
31. [31]
  Martin, T.; Verrier, C.; Hoarau, C.; Marsais, F. Org. Lett. 2008, 10, 2909. doi: 10.1021/ol801035c doi: 10.1021/ol801035c
32. [32]
  Joo, J. M.; Touré, B. B.; Sames, D. J. Org. Chem. 2010, 75, 4911. doi: 10.1021/jo100727j doi: 10.1021/jo100727j
33. [33]
  Strotman, N. A.; Chobanian, H. R.; Guo, Y.; He, J.; Wilson, J. E. Org. Lett. 2010, 12, 3578. doi: 10.1021/ol1011778 doi: 10.1021/ol1011778
34. [34]
  Théveau, L.; Verrier, C.; Lassalas, P.; Martin, T.; Dupas, G.; Querolle, O.; Hijfte, L. V.; Marsais, F.; Hoarau, C. Chem. Eur. J. 2011, 17, 14450. doi: 10.1002/chem.201101615 doi: 10.1002/chem.201101615
35. [35]
  Zhu, F.; Wang, Z. -X. Org. Lett. 2015, 17, 1601. doi: 10.1021/acs.orglett.5b00510 doi: 10.1021/acs.orglett.5b00510
36. [36]
  Kokornaczyk, A.; Schepmann, D.; Yamaguchi, J.; Itami, K.; Wünsch, B. Med. Chem. Commun. 2016, 7, 327. doi: 10.1039/C5MD00526D doi: 10.1039/C5MD00526D
37. [37]
  Hu, L. -Q.; Deng, R. -L.; Li, Y. -F.; Zeng, C. -J.; Shen, D. -S.; Liu, F. -S. Organometallics 2018, 37, 214. doi: 10.1021/acs.organomet.7b00784 doi: 10.1021/acs.organomet.7b00784
38. [38]
  Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467. doi: 10.1246/bcsj.71.467 doi: 10.1246/bcsj.71.467
39. [39]
  Kondo, Y.; Komine, T.; Sakamoto, T. Org. Lett. 2000, 2, 3111. doi: 10.1021/ol000183u doi: 10.1021/ol000183u
40. [40]
  Mori, A.; Sekiguchi, A.; Masui, K.; Shimada, T.; Horie, M.; Osakada, K.; Kawamoto, M.; Ikeda, T. J. Am. Chem. Soc. 2003, 125, 1700. doi: 10.1021/ja0289189 doi: 10.1021/ja0289189
41. [41]
  Bellina, F.; Cauteruccio, S.; Fiore, A. D.; Marchetti, C.; Rossi, R. Tetrahedron 2008, 64, 6060. doi: 10.1016/j.tet.2008.01.051 doi: 10.1016/j.tet.2008.01.051
42. [42]
  Tani, S.; Uehara, T. N.; Yamaguchi, J.; Itami, K. Chem. Sci. 2014, 5, 123. doi: 10.1039/C3SC52199K doi: 10.1039/C3SC52199K
43. [43]
  Gorelsky, S. I. Organometallics 2012, 31, 794. doi: 10.1021/om2012612 doi: 10.1021/om2012612
44. [44]
  Oh, K. H.; Kim, S. M.; Lee, M. J.; Park, J. K. Adv. Synth. Catal. 2015, 357, 3927. doi: 10.1002/adsc.201500726 doi: 10.1002/adsc.201500726
45. [45]
  Leow, D.; Li, G.; Mei, T. -S.; Yu, J. -Q. Nature 2012, 486, 518. doi: 10.1038/nature11158 doi: 10.1038/nature11158
46. [46]
  Yang, Y. -F.; Cheng, G. -J.; Liu, P.; Leow, D.; Sun, T. -Y.; Chen, P.; Zhang, X.; Yu, J. -Q.; Wu, Y. -D.; Houk, K. N. J. Am. Chem. Soc. 2014, 136, 344. doi: 10.1021/ja410485g doi: 10.1021/ja410485g
47. [47]
  Fang, L.; Saint-Denis, T. G.; Taylor, B. L. H.; Ahlquist, S.; Hong, K.; Liu, S.; Han, L.; Houk, K. N.; Yu, J. -Q. J. Am. Chem. Soc. 2017, 139, 10702. doi: 10.1021/jacs.7b03296 doi: 10.1021/jacs.7b03296
48. [48]
  Anand, M.; Sunoj, R. B.; Schaefer, H. F. J. Am. Chem. Soc. 2014, 136, 5535. doi: 10.1021/ja412770h doi: 10.1021/ja412770h
49. [49]
  Yoo, E. J.; Ma, S.; Mei, T. -S.; Chan, K. S. L.; Yu, J. -Q. J. Am. Chem. Soc. 2011, 133, 7652. doi: 10.1021/ja202563w doi: 10.1021/ja202563w
50. [50]
  Anand, M.; Sunoj, R. B.; Schaefer, H. F. ACS Catal. 2016, 6, 696. doi: 10.1021/acscatal.5b02639 doi: 10.1021/acscatal.5b02639
51. [51]
  Kleiman, J. P.; Dubeck, M. J. Am. Chem. Soc. 1963, 85, 1544. doi: 10.1021/ja00893a040 doi: 10.1021/ja00893a040
52. [52]
  Clement, N. D.; Cavell, K. J. Angew. Chem. Int. Ed. 2004, 43, 3845. doi: 10.1002/anie.200454166 doi: 10.1002/anie.200454166
53. [53]
  Kanyiva K. S.; Nakao, Y.; Hiyama, T. Angew. Chem. Int. Ed. 2007, 46, 8872. doi: 10.1002/anie.200703758 doi: 10.1002/anie.200703758
54. [54]
  Tobisu, M.; Hyodo, I.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 12070. doi: 10.1021/ja9053509 doi: 10.1021/ja9053509
55. [55]
  Hachiya, H.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem. Int. Ed. 2010, 49, 2202. doi: 10.1002/anie.200906996 doi: 10.1002/anie.200906996
56. [56]
  Vechorkin, O.; Proust, V.; Hu, X. Angew. Chem. Int. Ed. 2010, 49, 3061. doi: 10.1002/anie.200907040 doi: 10.1002/anie.200907040
57. [57]
  Yao, T.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem. Int. Ed. 2012, 51, 775. doi: 10.1002/anie.201106825 doi: 10.1002/anie.201106825
58. [58]
  Amaike, K.; Muto, K.; Yamaguchi, J.; Itami, K. J. Am. Chem. Soc. 2012, 134, 13573. doi: 10.1021/ja306062c doi: 10.1021/ja306062c
59. [59]
  Nett. A. J.; Zhao, W.; Zimmerman, P. M.; Montgomery, J. J. Am. Chem. Soc. 2015, 137, 7636. doi: 10.1021/jacs.5b04548 doi: 10.1021/jacs.5b04548
60. [60]
  Misal Castro, L. C.; Chatani, N. Chem. Lett. 2015, 44, 410. doi: 10.1246/cl.150024 doi: 10.1246/cl.150024
61. [61]
  Zhan, B.; Liu, B.; Hu, F.; Shi, B. Chin. Sci. Bull. 2015, 60, 2907. doi: 10.1360/N972015-00389 doi: 10.1360/N972015-00389
62. [62]
  Yang, X.; Shan, G.; Wang, L.; Rao, Y. Tetrahedron Lett. 2016, 57, 819. doi: 10.1016/j.tetlet.2016.01.009 doi: 10.1016/j.tetlet.2016.01.009
63. [63]
  Nakao, Y.; Kanyiva, K. S.; Hiyama, T. J. Am. Chem. Soc. 2008, 130, 2448. doi: 10.1021/ja710766j doi: 10.1021/ja710766j
64. [64]
  Tsai, C. -C.; Shih, W. -C.; Fang, C. -H.; Li, C. -Y.; Ong, T. -G.; Yap, G. P. A. J. Am. Chem. Soc. 2010, 132, 11887. doi: 10.1021/ja1061246 doi: 10.1021/ja1061246
65. [65]
  Nakao, Y.; Yamada, Y.; Kashihara, N.; Hiyama, T. J. Am. Chem. Soc. 2010, 132, 13666. doi: 10.1021/ja106514b doi: 10.1021/ja106514b
66. [66]
  Lee, W. -C.; Chen, C. -H.; Liu, C. -Y.; Yu, M. -S.; Lin, Y. -H.; Ong, T. -G. Chem. Commun. 2015, 51, 17104. doi: 10.1039/C5CC07455J doi: 10.1039/C5CC07455J
67. [67]
  Shih, W. -C.; Chen, W. -C.; Lai, Y. -C.; Yu, M. -S.; Ho, J. -J.; Yap, G. P. A.; Ong, T. -G. Org. Lett. 2012, 14, 2046. doi: 10.1021/ol300570f doi: 10.1021/ol300570f
68. [68]
  Lee, W. -C.; Wang, C. -H.; Lin, Y. -H.; Shih, W. -C.; Ong, T. -G. Org. Lett. 2013, 15, 5358. doi: 10.1021/ol402644y doi: 10.1021/ol402644y
69. [69]
  Liu, S.; Sawicki, J.; Driver, T. G. Org. Lett. 2012, 14, 3744. doi: 10.1021/ol301606y doi: 10.1021/ol301606y
70. [70]
  Yu, M. -S.; Lee, W. -C.; Chen, C. -H.; Tsai, F. -Y.; Ong, T. -G. Org. Lett. 2014, 16, 4826. doi: 10.1021/ol502314p doi: 10.1021/ol502314p
71. [71]
  Inoue, F.; Saito, T.; Semba, K.; Nakao, Y. Chem. Commun. 2017, 53, 4497. doi: 10.1039/C7CC00852J doi: 10.1039/C7CC00852J
72. [72]
  Okumura, S.; Nakao, Y. Asian J. Org. Chem. 2018, 7, 1355. doi: 10.1002/ajoc.201800208 doi: 10.1002/ajoc.201800208
73. [73]
  Wang, Y. -X.; Qi, S. -L.; Luan, Y. -X.; Han, X. -W.; Wang, S.; Chen, H.; Ye, M. J. Am. Chem. Soc. 2018, 140, 5360. doi: 10.1021/jacs.8b02547 doi: 10.1021/jacs.8b02547
74. [74]
  Nakao, Y.; Idei, H.; Kanyiva, K. S.; Hiyama, T. J. Am. Chem. Soc. 2009, 131, 15996. doi: 10.1021/ja907214t doi: 10.1021/ja907214t
75. [75]
  Tamura, R.; Yamada, Y.; Nakao, Y.; Hiyama, T. Angew. Chem. Int. Ed. 2012, 51, 5679. doi: 10.1002/anie.201200922 doi: 10.1002/anie.201200922
76. [76]
  Donets, P. A.; Cramer, N. Angew. Chem. Int. Ed. 2015, 54, 633. doi: 10.1002/anie.201409669 doi: 10.1002/anie.201409669
77. [77]
  Nakao, Y.; Idei, H.; Kanyiva, K. S.; Hiyama, T. J. Am. Chem. Soc. 2009, 131, 5070. doi: 10.1021/ja901153s doi: 10.1021/ja901153s
78. [78]
  Nakao, Y.; Morita, E.; Idei, H.; Hiyama, T. J. Am. Chem. Soc. 2011, 133, 3264. doi: 10.1021/ja1102037 doi: 10.1021/ja1102037
79. [79]
  Donets, P. A.; Cramer, N. J. Am. Chem. Soc. 2013, 135, 11772. doi: 10.1021/ja406730t doi: 10.1021/ja406730t
80. [80]
  Okumura, S.; Tang, S.; Saito, T.; Semba, K.; Sakaki, S.; Nakao, Y. J. Am. Chem. Soc. 2016, 138, 14699. doi: 10.1021/jacs.6b08767 doi: 10.1021/jacs.6b08767
81. [81]
  Okumura, S.; Nakao, Y. Org. Lett. 2017, 19, 584. doi: 10.1021/acs.orglett.6b03741 doi: 10.1021/acs.orglett.6b03741
82. [82]
  Okumura, S.; Komine, T.; Shigeki, E.; Semba, K.; Nakao, Y. Angew. Chem. Int. Ed. 2018, 57, 929. doi: 10.1002/anie.201710520 doi: 10.1002/anie.201710520
83. [83]
  Louillat, M.; Patureau, F. W. Org. Lett. 2013, 15, 164. doi: 10.1021/ol303216u doi: 10.1021/ol303216u
84. [84]
  Dikarev, E. V.; Gray, T. G.; Li, B. Angew. Chem. Int. Ed. 2005, 44, 1721. doi: 10.1002/anie.200462433 doi: 10.1002/anie.200462433
85. [85]
  Dikarev, E. V.; Li, B.; Zhang, H. T. J. Am. Chem. Soc. 2006, 128, 2814. doi: 10.1021/ja058294h doi: 10.1021/ja058294h
86. [86]
  Durivage, J. C.; Gruhn, N. E.; Li, B.; Dikarev, E. V.; Lichtenberger, D. L. J. Cluster Sci. 2008, 19, 275. doi: 10.1007/s10876-007-0179-9 doi: 10.1007/s10876-007-0179-9
87. [87]
  Hansen, J.; Li, B.; Dikarev, E.; Autschbach, J.; Davies, H. M. L. J. Org. Chem. 2009, 74, 6564. doi: 10.1021/jo900998s doi: 10.1021/jo900998s
88. [88]
  Yang, L.; Semba, K.; Nakao, Y. Angew. Chem. Int. Ed. 2017, 56, 4853. doi: 10.1002/anie.201701238 doi: 10.1002/anie.201701238
89. [89]
  Hu, Y.; Zhou, B.; Chen, H.; Wang, C. Angew. Chem. Int. Ed. 2018, 57, 12071. doi: 10.1002/anie.201806287 doi: 10.1002/anie.201806287
90. [90]
  Zhou, B.; Hu, Y.; Liu, T.; Wang, C. Nat. Commun. 2017, 8, 1169. doi: 10.1038/s41467-017-01262-4 doi: 10.1038/s41467-017-01262-4
91. [91]
  Zhou, B.; Hu, Y.; Wang, C. Angew. Chem. Int. Ed. 2015, 54, 13659. doi: 10.1002/anie.201506187 doi: 10.1002/anie.201506187
92. [92]
  Negishi, E.; Kondakov, D. Y.; Choueiry, D.; Kasai, K.; Takahashi, T. J. Am. Chem. Soc. 1996, 118, 9577. doi: 10.1021/ja9538039 doi: 10.1021/ja9538039
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沈阳化工大学材料科学与工程学院沈阳 110142