Citation: Rui Yan, Hu Chen, Ming Zhao. C—C Cross Coupling Reaction Based on Olefinic C-H Bond Activation[J]. University Chemistry, ;2024, 39(1): 87-94. doi: 10.3866/PKU.DXHX202306052 shu

C—C Cross Coupling Reaction Based on Olefinic C-H Bond Activation

Rui Yan ^1,2 ,
Hu Chen ¹ ,
Ming Zhao ^1,,

1.
Anhui Engineering Laboratory for Medicinal and Food Homologous Natural Resources Exploration, College of Chemistry and Pharmacy Engineering, Hefei Normal University, Hefei 230601, China;
2.
CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China

Corresponding author: Ming Zhao, zhaomnwu@126.com
Received Date: 27 June 2023

Olefins are a very important class of compounds, which can be transformed to various complex organic molecules through a series of transformations. In this paper, C-C cross coupling reaction based on olefinic C-H bond activation is described in detail. Based on the activation of C-H bonds, C-C bonds are constructed through C-C cross coupling reaction by transition metal catalysts such as Rh, Pd and Co. This introduction of olefinic C-H bond activation can enrich and expand the knowledge of olefins in organic chemistry courses, and it is also helpful for students to understand the forefront of organic chemistry development, stimulate their learning enthusiasm and initiative, and cultivate their scientific research literacy.
- Transition metal catalysis,
- C-H bond activation,
- Olefins,
- Coupling reaction
1. [1]
2. [2]
  Sigman, M. S.; Werner, E. W. Acc. Chem. Res. 2012, 45, 874.
3. [3]
  Colby, D. A.; Bergman, R. G.; Ellman, J. A.; Chem. Rev. 2010, 110, 624.
4. [4]
  Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814.
5. [5]
  Gung, B. W.; Kumi, G. J. Org. Chem. 2004, 69, 3488.
6. [6]
  Fontana, A.; d’lppolito, G.; D’Souza, L.; Mollo, E.; Parameswaram, P. S.; Cimino, G. J. Nat. Prod. 2001, 64, 131.
7. [7]
  Kong, J. R.; Ngai, M. Y.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 718.
8. [8]
  Miller, K. M.; Luanphaisarnnont, T.; Molinaro, C.; Jamison, T. F; J. Am. Chem. Soc. 2004, 126, 4130.
9. [9]
  Finkbeiner, P.; Kloeckner, U.; Nachtsheim, B. J. Angew. Chem. Int. Ed. 2015, 54, 4949.
10. [10]
  Caspers, L. D.; Finkbeiner, P.; Nachtsheim, B. J. Chem. Eur. J. 2017, 23, 2748.
11. [11]
  Feng, C.; Feng, D.; Luo, Y.; Loh, T. P. Org. Lett. 2014, 16, 5956.
12. [12]
  Xu, Y.; Zhang, Q.; He, T.; Meng, F.; Loh, T. P. Adv. Synth. Catal. 2014, 356, 1539.
13. [13]
  Negishi, E. Angew. Chem. Int. Ed. 2011, 50, 6738.
14. [14]
  Kuttruff, C. A.; Geiger, S.; Cakmak, M.; Mayer, P.; Trauner, D. Org. Lett. 2012, 14, 1070.
15. [15]
  Hubert, P.; Seibel, E.; Beemelmanns, C.; Campagne, J.-M.; Figueiredo, R. M. Adv. Synth. Catal. 2020, 362, 5532.
16. [16]
  Soengas, R. G.; Rodríguez-Solla, H. Molecules 2021, 26, 249.
17. [17]
  Wen, Z.-K.; Xu, Y.-H.; Loh, T.-P. Chem. Sci. 2013, 4, 4520.
18. [18]
  Zhong, X.-M.; Cheng, G.-J.; Chen, P.; Zhang, X.; Wu, Y.-D. Org. Lett. 2016, 18, 5240.
19. [19]
  Zhang, X.; Wang, M.; Zhang, M.-X.; Xu, Y.-H.; Loh, T.-P. Org. Lett. 2013, 15, 5531.
20. [20]
  Xu, Y.-H.; Lu, J.; Loh, T.-P. J. Am. Chem. Soc. 2009, 131, 1372.
21. [21]
  Xu, Y.-H.; Wang, W.-J.; Wen, Z.-K.; Hartley, J. J.; Loh, T.-P. Tetrahedron Lett. 2010, 51, 3504.
22. [22]
  Zhang, Y.; Cui, Z.; Li, Z.; Liu, Z.-Q. Org. Lett. 2012, 14, 1838.
23. [23]
  Boultadakis-Arapinis, M.; Hopkinson, M. N.; Glorius, F. Org. Lett. 2014, 16, 1630.
24. [24]
  Liang, Q.-J.; Yang, C.; Meng, F.-F.; Jiang, B.; Xu, Y.-H.; Loh, T.-P. Angew. Chem. Int. Ed. 2017, 56, 5091.
25. [25]
  Misha, N. K.; Sharma, S.; Park, J.; Han, S.; Kim, I. S. ACS Catal. 2017, 7, 2821.
26. [26]
  Gensch, T.; Vásquez-Céspedes, S.; Yu, D.-G.; Glorius, F. Org. Lett. 2015, 17, 3714.
27. [27]
  Kim, M.; Han, S. H.; Kim, I. S. Chem. Commun. 2014, 50, 11303.
28. [28]
  Wu, X.; Ji, H. Org. Chem. 2018, 83, 12094.
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