Citation: Wang Zhenrong, Xie Peipei, Xia Yuanzhi. Recent progress in Ru(Ⅱ)-catalyzed C-H activations with oxidizing directing groups[J]. Chinese Chemical Letters, ;2018, 29(1): 47-53. doi: 10.1016/j.cclet.2017.06.018 shu

Recent progress in Ru(Ⅱ)-catalyzed C-H activations with oxidizing directing groups

College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China

Author Bio:

Yuanzhi Xia completed his bachelor degree at Hubei University in 2004 and obtained his Ph.D. degree from the Graduate University of Chinese Academy of Sciences in 2009, working with Profs. Zhi-Xiang Yu and Yahong Li. After that, he was appointed to a lectureship at Wenzhou University, and was promoted to full Professor in 2016 and director of the chemistry department in 2017. He was a visiting scientist in the research group of Prof. Bernhard Breit at the University of Freiburg, Germany, from 2013 to 2015. His research focuses on mechanistic investigation of organic and organometallic transformations by DFT calculations and development of new synthetic methodology.
Corresponding author: Xia Yuanzhi, xyz@wzu.edu.cn
Received Date: 10 May 2017
Revised Date: 27 May 2017
Accepted Date: 14 June 2017
Available Online: 15 January 2017

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In this review, we highlight the recent development in Ru(Ⅱ)-catalyzed C-H activations under redox neutral conditions. After a brief introduction of the C-H activations with oxidizing direct group by different transition metal catalysts, the examples with Ru(Ⅱ) catalyst were classified and introduced according to different internal oxidants used in the system. The features of each methodology will be highlighted and the plausible reaction mechanism will be presented if available.
- Ru (Ⅱ) catalysis,
- C-H activation,
- Redox neutral condition,
- Oxidizing directing group,
- Internal oxidant
1. [1]
  (a) B. Song, B. Xu, Chem. Soc. Rev. 46(2017) 1103-1123;
  (b) G. Qiu, J. Wu, Org. Chem. Front. 2(2015) 169-178;
  (c) W. Liu, L. Ackermann, ACS Catal. 6(2016) 3743-3752;
  (d) Z. Chen, B. Wang, J. Zhang, et al., Org. Chem. Front. 2(2015) 1107-1295;
  (e) P. L. Arnold, M. W. McMullon, J. Rieb, F. E. Kühn, M. Angew, Chem. Int. Ed. 54(2015) 82-100;
  (f) Zhang, Y. Zhang, X. Jie, et al., Org. Chem. Front. 1(2014) 843-895.
2. [2]
  (a) H. Huang, X. Ji, W. Wu, H. Jiang, Chem. Soc. Rev. 44(2015) 1155-1171;
  (b) J. Mo, L. Wang, Y. Liu, X. Cui, Synthesis 47(2015) 439-459;
  (c) T. Gensch, M. N. Hopkinson, F. Glorius, J. Wencel-Delord, Chem. Soc. Rev. 45(2016) 2900-2936.
3. [3]
  T. Gerfaud, L. Neuville, J. Zhu, J. Angew, Chem. Int. Ed. 48(2009) 572-577. doi: 10.1002/anie.v48:3
4. [4]
  (a) J. Wu, X. Cui, L. Chen, G. Jiang, Y. Wu, J. Am. Chem. Soc. 131(2009) 13888-13889;
  (b) Y. Tan, J. F. Hartwig, J. Am. Chem. Soc. 132(2010) 3676-3677.
5. [5]
  (a) S. Rakshit, C. Grohmann, T. Besset, F. Glorius, J. Am. Chem. Soc. 133(2011) 2350-2353;
  (b) N. Guimond, S. I. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 133(2011) 6449-6457;
  (c) N. Guimond, C. Gouliaras, K. Fagnou, J. Am. Chem. Soc. 132(2010) 6908-6909.
6. [6]
  (a) S. Yu, S. Liu, Y. Lan, B. Wan, X. Li, J. Am. Chem. Soc. 137(2015) 1623-1631;
  (b) S. Wu, R. Zeng, C. Fu, et al., Chem. Sci. 6(2015) 2275-2285;
  (c) T. Piou, T. Rovis, J. Am. Chem. Soc. 136(2014) 11292-11295;
  (d) T. K. Hyster, D. M. Dalton, T. Rovis, Chem. Sci. 6(2015) 254-258;
  (e) S. Cui, Y. Zhang, D. Wang, Q. Wu, Chem. Sci. 4(2013) 3912-3916;
  (f) H. Zhang, K. Wang, B. Wang, et al., Angew. Chem. Int. Ed. 53(2014) 13234-13238.
7. [7]
  (a) J. Chen, W. Guo, Y. Xia, J. Org. Chem. 81(2016) 2635-2638;
  (b) W. Guo, Y. Xia, J. Org. Chem. 80(2015) 8113-8121;
  (c) W. Guo, T. Zhou, Y. Xia, Organometallics 34(2015) 3012-3020;
  (d) T. Zhou, W. Guo, Y. Xia, Chem. Eur. J. 21(2015) 9209-9218;
  (e) L. Xu, Q. Zhu, G. Huang, B. Cheng, Y. Xia, J. Org. Chem. 77(2012) 3017-3024.
8. [8]
  (a) Y. Yang, K. N. Houk, Y. Wu, J. Am. Chem. Soc. 138(2016) 6861-6868;
  (b) S. R. Neufeldt, G. Jimene'z-Ose's, J. R. Huckins, O. R. Thiel, K. N. Houk, J. Am. Chem. Soc. 137(2015) 9843-9854;
  (c) M. Zhang, G. Huang, Chem. Eur. J. 22(2016) 9356-9365;
  (d) W. Chen, Z. Lin, Organometallics 34(2015) 309-318.
9. [9]
  (a) A. A. Kulkarni, O. Daugulis, Synthesis 24(2009) 4087-4109;
  (b) K. Gao, N. Yoshikai, Acc. Chem. Res. 47(2014) 1208-1219;
  (c) R. Hess, J. Treutwein, G. Hilt, Synthesis 22(2008) 3537-3562;
  (d) M. Moselage, J. Li, L. Ackermann, ACS Catal. 6(2016) 498-525;
  (e) P. Gandeepan, C. Cheng, Acc. Chem. Res. 48(2015) 1194-1206.
10. [10]
  (a) L. Ackermann, Acc. Chem. Res. 47(2014) 281-295;
  (b) C. Bruneau, P. H. Dixneuf, Top. Organomet. Chem. 55(2016) 137-188;
  (c) S. Dana, M. R. Yadav, A. K. Sahoo, Top. Organomet. Chem. 55(2016) 189-216;
  (d) P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 112(2012) 5879-5918.
11. [11]
  Bin. Li, H. Feng, S. Xu, B. Wang, Chem. Eur. J. 17(2011) 12573-12577. doi: 10.1002/chem.201102445
12. [12]
  L. Ackermann, A.V. Lygin, N. Hofmann, Angew. Chem. Int. Ed. 50(2011) 6379-6382. doi: 10.1002/anie.201101943
13. [13]
  L. Ackermann, S. Fenner, Org. Lett. 13(2011) 6548-6551. doi: 10.1021/ol202861k
14. [14]
  F. Yang, L. Ackermann, J. Org. Chem. 79(2014) 12070-12082. doi: 10.1021/jo501884v
15. [15]
  B. Li, J. Ma, N. Wang, et al., Org. Lett. 14(2012) 736-739. doi: 10.1021/ol2032575
16. [16]
  S. Nakanowatari, L. Ackermann, Chem. Eur. J. 21(2015) 16246-16251. doi: 10.1002/chem.201502785
17. [17]
  K.K. Gollapelli, S. Kallepu, N. Govindappa, J.B. Nanubolub, R. Chegondi, Chem. Sci. 7(2016) 4748-4753. doi: 10.1039/C6SC01456A
18. [18]
  T.Y. Fukui, P. Liu, Q. Liu, et al., J. Am. Chem. Soc. 136(2014) 15607-15614. doi: 10.1021/ja5072702
19. [19]
  X. Wu, B. Wang, S. Zhou, Y. Zhou, H. Liu, ACS Catal. 7(2017) 2494-2499. doi: 10.1021/acscatal.7b00031
20. [20]
  X. Wu, B. Wang, Y. Zhou, H. Liu, Org. Lett. 19(2017) 1294-1297. doi: 10.1021/acs.orglett.7b00089
21. [21]
  C. Kornhaaß, J. Li, L. Ackermann, J. Org. Chem. 77(2012) 9190-9198. doi: 10.1021/jo301768b
22. [22]
  R.K. Chinnagolla, S. Pimparkar, M. Jeganmohan, Org. Lett.14(2012) 3032-3035. doi: 10.1021/ol301091z
23. [23]
  R.K. Chinnagolla, S. Pimparkar, M. Jeganmohan, Chem. Commun. 49(2013) 3703-3705. doi: 10.1039/c3cc41269e
24. [24]
  C. Kornhaaß, C. Kuper, L. Ackermanna, Adv. Synth. Catal. 356(2014) 1619-1624. doi: 10.1002/adsc.v356.7
25. [25]
  Z. Zhou, G. Liu, Y. Shen, X. Lu, Org. Chem. Front. 1(2014) 1161-1165. doi: 10.1039/C4QO00196F
26. [26]
  (a) G. Liu, Y. Shen, Z. Zhou, X. Lu, Angew. Chem. 125(2013) 6149-6153;
  (b) Y. Shen, G. Liu, Z. Zhou, X. Lu, Org. Lett. 15(2013) 3366-3369.
27. [27]
  Z. Zhang, H. Jiang, Y. Huang, Org. Lett. 16(2014) 5976-5979. doi: 10.1021/ol502998n
28. [28]
  S. Zhou, J. Wang, P. Chen, K. Chen, J. Zhu, Chem. Eur. J. 22(2016) 14508-14512. doi: 10.1002/chem.201602936
29. [29]
  P.P. Kaishap, B. Sarma, S. Gogoi, Chem. Commun. 52(2016) 9809-9812. doi: 10.1039/C6CC04461A
30. [30]
  J. Zhang, A. Ugrinov, P. Zhao, Angew. Chem. Int. Ed. 52(2013) 6681-6684. doi: 10.1002/anie.v52.26
31. [31]
  D.N. Tran, N. Cramer, Angew. Chem. Int. Ed. 50(2011) 11098-11102. doi: 10.1002/anie.v50.47
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