Citation: Liu Yuanhua, Dong Xiu-Qin, Zhang Xumu. Recent Advances of Nickel-Catalyzed Homogeneous Asymmetric Hydrogenation[J]. Chinese Journal of Organic Chemistry, ;2020, 40(5): 1096-1104. doi: 10.6023/cjoc201912025 shu

Recent Advances of Nickel-Catalyzed Homogeneous Asymmetric Hydrogenation

a.
Key Laboratory of Biomedical Polymers, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072
b.
Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong 518055

Corresponding author: Dong Xiu-Qin, xiuqindong@whu.edu.cn
Received Date: 19 December 2019
Revised Date: 20 January 2020
Available Online: 31 May 2020
Fund Project: the National Natural Science Foundation of Jiangsu Province SBK2019041078the Wuhan Morning Light Plan of Youth Science 2017050300307the National Natural Science Foundation of China 21502145Project supported by the National Natural Science Foundation of China (No. 21502145), the Wuhan Morning Light Plan of Youth Science and Technology (No. 2017050300307) and the National Natural Science Foundation of Jiangsu Province (No. SBK2019041078)

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Transition metal complexes-catalyzed homogeneous asymmetric hydrogenation is an important method for the synthesis of chiral compounds. At present, it is mainly focused on precious transition metal catalytic systems, such as ruthenium, rhodium, iridium and palladium. However, they are suffered from the difficulties of limited resource, high cost and environmental contamination. Therefore, it is important and necessary to develop catalytic systems based on cheap, non-toxic or low toxic, environmentally friendly and earth-abundant iron, cobalt, nickel, copper transition metal, which are in accordance with the requirements and research trend of the sustainable development of modern chemistry. The recent progress of nickel-catalyzed homogeneous asymmetric hydrogenation of prochiral unsaturated compounds containing carbon oxygen double bond (C=O), carbon carbon double bond (C=C) and carbon nitrogen double bond (C=N) is reviewed, and some breakthroughs and considerable research results achieved are introduced. In addition, the advantages and disadvantages of different types of substrates in nickel catalyst system are analyzed, and the future research direction is prospected.
- asymmetric hydrogenation,
- nickel catalysis,
- chiral diphosphine ligand,
- chiral compounds,
- stereoselectivity
1. [1]
2. [2]
  (a) Morris, R. H. Chem. Soc. Rev. 2009, 38, 2282.
  (b) Morris, R. H. Acc. Chem. Res. 2015, 48, 1494.
  (c) Chirik, P. J. Acc. Chem. Res. 2015, 48, 1687.
  (d) Li, Y.-Y.; Yu, S.-L.; Shen, W.-Y.; Gao, J.-X. Acc. Chem. Res. 2015, 48, 2587.
  (e) Harman, W. H.; Peters, J. C. Chem. Rev. 2015, 115, 3170.
  (f) Zhang, Z.; Butt, N. A.; Zhou, M.; Liu, D.; Zhang, W. Chin. J. Chem. 2018, 36, 443.
3. [3]
  (a) Tai, A. and Sugimura, T. In Chiral Catalysts Immobilization and Recycling, Eds.: De Vos, D. E.; Vankelecom, I. F. J.; Jacobs, P. A., Wiley-VCH, Weinheim, 2000.
  (b) Sarko, C. R.; DiMare, M.; Yus, M.; Alonso, F. e-EROS Encyclopedia of Reagents for Organic Synthesis, Wiley-VCH, Weinheim 2014.
  (c) Angulo, I. M.; Kluwer, A. M.; Bouwman, E. Chem. Commun. 1998, 2689.
  (d) Angulo, I. M.; Bouwman, E.; van Gorkum, R.; Lok, S. M.; Lutz, M.; Spek, A. L. J. Mol. Catal. A: Chem. 2003, 202, 97.
  (e) Harman, W. H.; Peters, J. C. J. Am. Chem. Soc. 2012, 134, 5080.
  (f) Cammarota, R. C.; Lu, C. C. J. Am. Chem. Soc. 2015, 137, 12486.
4. [4]
  Shevlin, M.; Friedfeld, M. R.; Sheng, H.; Pierson, N. A.; Hoyt, J. M.; Campeau, L.; Chirik, P. J. J. Am. Chem. Soc. 2016, 138, 3562. doi: 10.1021/jacs.6b00519
5. [5]
  Hamada, Y.; Koseki, Y.; Fujii, T.; Maeda, T.; Hibino, T.; Makino, K. Chem. Commun. 2008, 6206.
6. [6]
  Hibino, T.; Makino, K.; Sugiyama, T.; Hamada, Y. ChemCatChem 2009, 1, 237. doi: 10.1002/cctc.200900084
7. [7]
  Dong, Z. R.; Li, Y. Y.; Yu, S. L.; Sun, G. S.; Gao, J. X. Chin. Chem. Lett. 2012, 23, 533. doi: 10.1016/j.cclet.2012.02.005
8. [8]
  Corma, A.; Iglesias, M.; Del Pino, C.; Sanchez, F. J. Organomet. Chem. 1992, 431, 233. doi: 10.1016/0022-328X(92)80121-D
9. [9]
  Yang, P.; Xu, H.; Zhou, J. Angew. Chem., Int. Ed. 2014, 53, 12210. doi: 10.1002/anie.201407744
10. [10]
  Guo, S. Y.; Yang, P.; Zhou, J. Chem. Commun. 2015, 51, 12115. doi: 10.1039/C5CC01632K
11. [11]
  Guo, S.; Zhou, J. Org. Lett. 2016, 18, 5344. doi: 10.1021/acs.orglett.6b02662
12. [12]
  Gao, W.; Lv, H.; Zhang, T.; Yang, Y.; Chung, L. W.; Wu, Y.; Zhang, X. Chem. Sci. 2017, 8, 6419. doi: 10.1039/C7SC02669B
13. [13]
  Li, X.; You, C.; Li, S.; Lv, H.; Zhang, X. Org. Lett. 2017, 19, 5130. doi: 10.1021/acs.orglett.7b02417
14. [14]
  Long, J.; Gao, W.; Guan, Y.; Lv, H.; Zhang, X. Org. Lett. 2018, 20, 5914. doi: 10.1021/acs.orglett.8b02579
15. [15]
  Han, Z.; Liu, G.; Zhang, X.; Li, A.; Dong, X.-Q.; Zhang, X. Org. Lett. 2019, 21, 3923. doi: 10.1021/acs.orglett.9b00994
16. [16]
  Guan, Y.; Han, Z.; Li, X.; You, C.; Tan, X.; Lv, H.; Zhang, X. Chem. Sci. 2019, 10, 252. doi: 10.1039/C8SC04002H
17. [17]
  You, C.; Li, X.; Gong, Q.; Wen, J.; Zhang, X. J. Am. Chem. Soc. 2019, 141, 14560. doi: 10.1021/jacs.9b07957
18. [18]
  Xu, H.; Yang, P.; Chuanprasit, P.; Hirao, H.; Zhou, J. Angew. Chem., Int. Ed. 2015, 54, 5112. doi: 10.1002/anie.201501018
19. [19]
  Yang, P.; Lim, L. H.; Chuanprasit, P.; Hirao, H.; Zhou, J. Angew. Chem., Int. Ed. 2016, 55, 12083. doi: 10.1002/anie.201606821
20. [20]
  Zhao, X.; Xu, H.; Huang, X.; Zhou, J. Angew. Chem., Int. Ed. 2019, 58, 292. doi: 10.1002/anie.201809930
21. [21]
  Li, B.; Chen, J.; Zhang, Z.; Gridnev, I. D.; Zhang, W. Angew. Chem., Int. Ed. 2019, 58, 7329. doi: 10.1002/anie.201902576
22. [22]
  Liu, Y.; Yi, Z.; Tan, X.; Dong, X.-Q.; Zhang, X. iScience 2019, 19, 63. doi: 10.1016/j.isci.2019.07.004
23. [23]
  Zhao, X.; Zhang, F.; Liu, K.; Zhang, X.; Lv, H. Org. Lett. 2019, 21, 8966. doi: 10.1021/acs.orglett.9b03365
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