Citation: Wu Jinwen, Zhu Jiawen, Li Hui, Wu Chunlei, Shen Runpu, Yu Lemao. Recent Advances of Transition Metal-Catalyzed Aerobic Oxygenation with Molecular Oxygen[J]. Chinese Journal of Organic Chemistry, ;2019, 39(12): 3328-3337. doi: 10.6023/cjoc201907005 shu

Recent Advances of Transition Metal-Catalyzed Aerobic Oxygenation with Molecular Oxygen

College of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing, Zhejiang 312000

Corresponding author: Shen Runpu, srunpu@usx.edu.cn Yu Lemao, yulm@usx.edu.cn
Received Date: 3 July 2019
Revised Date: 11 August 2019
Available Online: 30 December 2019
Fund Project: the Public Projects of Zhejiang Province of China LGG19B02002the Doctoral Research Initiation Fund of Shaoxing University 20185018Project supported by the Public Projects of Zhejiang Province of China (No. LGG19B02002) and the Doctoral Research Initiation Fund of Shaoxing University (No. 20185018)

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Oxygen-bearing structures are attractive synthetic targets due to their wide presence in a great number of natural products and biologically active molecules, and their role as useful synthons in organic synthesis. Thus, the preparation of O-bearing compounds has been an important topic. Transition metal-catalyzed aerobic oxygenation strategy has emerged as a novel and efficient methodology for constructing C-C bonds and C-heteroatom bonds. This strategy has become one of the most important and useful synthetic method in organic synthesis of O-bearing compounds. Based on the previous work of our group and others, herein, the new applications of transition metal-catalyzed oxygenation of C-H bond activation and C-C bond cleavage with oxygen as oxygen source are discussed. The recent progress in trans-metal catalytic oxygen insertion of ketones, aldehydes, alkene, alkynes, arene and aromatic heterocyclic compounds has been reviewed. Transition metal-catalysts can initiate oxygen insertion reaction of free radical pathway and realize selective insertion of oxygen radicals under oxygen oxidation. These reactions are characterized by mild conditions, environmental protection and highly atom economy.
- transition metal catalysis,
- oxygen oxidation,
- C-H activation,
- C-C cleavage,
- oxygenated reaction,
- radical pathway
1. [1]
  Yin, Z.; Wang, Z.; Wu, X. F. Chin. J. Org. Chem. 2019, 39, 573(in Chinese).
2. [2]
  Zhang, Y.; Riemer, D.; Schilling, W.; Kollmann, J.; Das, S. ACS Catal. 2018, 8, 6659. doi: 10.1021/acscatal.8b01897
3. [3]
  Thatikonda, T.; Deepake, S. K.; Das, U. Org. Lett. 2019, 21, 2523. doi: 10.1021/acs.orglett.9b00115
4. [4]
  Yuan, S.; Wang, Y.; Qiu, G.; Liu, J. B. Chin. J. Org. Chem. 2017, 37, 566(in Chinese).
5. [5]
  Liang, Y. F.; Jiao, N. Acc. Chem. Res. 2017, 50, 1064.
6. [6]
  Zhang, L.; Ang, G. Y.; Chiba, S. Org. Lett. 2011, 13, 1622. doi: 10.1021/ol200425c
7. [7]
  Wang, Y. F.; Chen, H.; Zhu, X.; Chiba, S. J. Am. Chem. Soc. 2012, 134, 11980. doi: 10.1021/ja305833a
8. [8]
  Zhang, C.; Xu, Z.; Zhang, L.; Jiao, N. Angew. Chem., Int. Ed. 2011, 50, 11088. doi: 10.1002/anie.201105285
9. [9]
  Zhang, C.; Zhang, L.; Jiao, N. Adv. Synth. Catal. 2012, 354, 1293. doi: 10.1002/adsc.201100892
10. [10]
  Xu, Z.; Zhang, C.; Jiao, N. Angew. Chem., Int. Ed. 2012, 51, 11367. doi: 10.1002/anie.201206382
11. [11]
  Huang, X.; Li, X.; Zou, M.; Pan, J.; Jiao, N. Org. Chem. Front. 2015, 2, 354. doi: 10.1039/C5QO00028A
12. [12]
  Kumar, Y.; Jaiswal, Y.; Kumar, A. J. Org. Chem. 2016, 81, 12247. doi: 10.1021/acs.joc.6b02176
13. [13]
  Xu, X.; Li, B.; Zhao, Y.; Song, Q. Org. Chem. Front. 2017, 4, 331. doi: 10.1039/C6QO00635C
14. [14]
  Chen, X. L.; Peng, Y. H.; Li, Y.; Wu, M. H.; Guo, H. B.; Wang, J.; Sun, S. F. RSC Adv. 2017, 7, 18588. doi: 10.1039/C7RA02207G
15. [15]
  Wang, Y.; Liu, H. X.; Zhang, X. F.; Zhang, Z. L.; Huang, D. G. Org. Biomol. Chem. 2017, 15, 9164. doi: 10.1039/C7OB02192E
16. [16]
  Su, Y.; Sun, X.; Wu, G.; Jiao, N. Angew. Chem., Int. Ed. 2013, 52, 9808. doi: 10.1002/anie.201303917
17. [17]
  Sun, X.; Li, X.; Song, S.; Zhu, Y.; Liang, Y.-F.; Jiao, N. J. Am. Chem. Soc. 2015, 137, 6059. doi: 10.1021/jacs.5b02347
18. [18]
  Lu, Q. Q.; Liu, Z. L.; Luo, Y.; Zhang, G. H.; Huang, Z. Y.; Wang, H. M.; Liu, C.; Miller, J. T.; Lei, A. W. Org. Lett. 2015, 17, 3402. doi: 10.1021/acs.orglett.5b01223
19. [19]
  Zhou, H.; Chen, Z. Y. Chin. J. Org. Chem. 2018, 38, 719(in Chinese).
20. [20]
  Wei, W.; Liu, C. L.; Yang, D. S.; Wen, J. W.; You, J. M.; Suo, Y. R.; Wang, H. Chem. Commun. 2013, 49, 10239. doi: 10.1039/c3cc45803b
21. [21]
  Wei, W.; Wen, J. W.; Yang, D. S.; Wu, M.; You, J. M.; Wang, H. Org. Biomol. Chem. 2014, 12, 7678. doi: 10.1039/C4OB01369G
22. [22]
  Gao, W. C.; Cheng, Y. F.; Shang, Y. Z.; Chang, H. H.; Li, X.; Zhou, R.; Qiao, Y.; Wei, W. L. J. Org. Chem. 2018, 83, 11956. doi: 10.1021/acs.joc.8b01843
23. [23]
  Toh, K. K.; Wang, Y.-F.; Ng, E. P. J.; Chiba, S. J. Am. Chem. Soc. 2011, 133, 13942. doi: 10.1021/ja206580j
24. [24]
  Qian, S. P.; Ma, Y. R.; Gao, S. S.; Luo, J. F. Chin. J. Org. Chem. 2018, 38, 1930(in Chinese).
25. [25]
  Zhang, Y. H.; Yu, J. Q. J. Am. Chem. Soc. 2009, 131, 14654. doi: 10.1021/ja907198n
26. [26]
  Yan, Y.; Feng, P.; Zheng, Q.-Z.; Liang, Y.-F.; Lu, J.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2013, 52, 5827. doi: 10.1002/anie.201300957
27. [27]
  Chiba, S.; Zhang, L.; Lee, J.-Y. J. Am. Chem. Soc. 2010, 132, 7266. doi: 10.1021/ja1027327
28. [28]
  Tnay, Y. L.; Chen, C.; Chua, Y. Y.; Zhang, L.; Chiba, S. Org. Lett. 2012, 14, 3550. doi: 10.1021/ol301583y
29. [29]
  Liang, Y.-F.; Li, X.; Wang, X.; Yan, Y.; Feng, P.; Jiao, N. ACS Catal. 2015, 5, 1956. doi: 10.1021/cs502126n
30. [30]
  Li, Z.; Huang, X.; Chen, F.; Zhang, C.; Wang, X.; Jiao, N. Org. Lett. 2015, 17, 584. doi: 10.1021/ol5035996
31. [31]
  Wu, W.; Xu, J.; Huang, S.; Su, W. Chem. Commun. 2011, 47, 9660. doi: 10.1039/c1cc10545k
32. [32]
  Bao, Y.-H.; Zhu, J.-Y.; Qin, W.-B.; Kong, Y.-B.; Chen, Z.-W.; Tang, S.-B.; Liu, L.-X. Org. Biomol. Chem. 2013, 11, 7938. doi: 10.1039/c3ob41589a
33. [33]
  Wang, C.; Zhang, L. P.; Ran, A.; Lu, P.; Wang, Y. G. Org. Lett. 2013, 15, 2982. doi: 10.1021/ol401144m
34. [34]
  Huang, H.; Cai, J.; Ji, X.; Xiao, F.; Chen, Y.; Deng, G. J. Angew. Chem. 2016, 128, 315. doi: 10.1002/ange.201508076
35. [35]
  Guo, S. H.; Wang, F.; Tao, L.; Zhang, X. Y.; Fan, X. S. J. Org. Chem. 2018, 83, 3889. doi: 10.1021/acs.joc.8b00231
36. [36]
  Zhang, J.; Kohlbouni, S. T.; Borban, B. Org. Lett. 2019, 21, 14. doi: 10.1021/acs.orglett.8b03185
37. [37]
  Yu, L. M.; Zhong, Y.; Yu, J. C.; Gan, L.; Cai, Z. J.; Wang, R.; Jiang, X. X. Chem. Commun. 2018, 54, 2353. doi: 10.1039/C7CC09640B
38. [38]
  Yu, L. M. Ph. D. Dissertation, Sun Yat-Sen University, Guangzhou, 2018 (in Chinese).
39. [39]
  Zhang, C.; Jiao, N. J. Am. Chem. Soc. 2010, 132, 28. doi: 10.1021/ja908911n
40. [40]
  Wang, J.; Wang, J.; Zhu, Y.; Lu, P.; Wang, Y. Chem. Commun. 2011, 47, 3275. doi: 10.1039/c0cc04922k
41. [41]
  Toh, K. K.; Sanjaya, S.; Sahnoun, S.; Chong, S. Y.; Chiba, S. Org. Lett. 2012, 9, 2290.
42. [42]
  Ling, F.; Li, Z. X.; Zhang, C. G.; Liu, X.; Ma, C. J. Am. Chem. Soc. 2014, 136, 10914. doi: 10.1021/ja506795u
43. [43]
  Ling, F.; Wan, Y.; Wang, D.; Ma, C. J. Org. Chem. 2016, 81, 2770. doi: 10.1021/acs.joc.5b02870
44. [44]
  Liu, X.; Mao, R. J.; Ma, C. Org. Lett. 2017, 19, 6704. doi: 10.1021/acs.orglett.7b03427
45. [45]
  Pan, J.; Li, X. Y.; Qiu, X.; Luo, X.; Jiao, N. Org. Lett. 2018, 20, 2762. doi: 10.1021/acs.orglett.8b00992
46. [46]
  Zhang, C.; Xu, Z.; Shen, T.; Wu, G.; Zhang, L.; Jiao, N. Org. Lett. 2012, 14, 2362. doi: 10.1021/ol300781s
47. [47]
  Zhang, C.; Feng, P.; Jiao, N. J. Am. Chem. Soc. 2013, 135, 15257. doi: 10.1021/ja4085463
48. [48]
  Huang, X.; Li, X.; Zou, M.; Song, S.; Tang, C.; Yuan, Y.; Jiao, N. J. Am. Chem. Soc. 2014, 136, 14858. doi: 10.1021/ja5073004
49. [49]
  Liu, C.; Yang, Z.; Zeng, Y.; Fang, Z.; Guo, K. Org. Chem. Front. 2017, 4, 2375. doi: 10.1039/C7QO00690J
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