Recent Advances of Nickel-Catalyzed Homogeneous Asymmetric Hydrogenation

doi:10.6023/cjoc201912025

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (5): 1096-1104.DOI: 10.6023/cjoc201912025 Previous Articles Next Articles

Special Issue: 镍催化有机反应虚拟合辑

镍催化均相不对称氢化反应研究进展

刘元华^a, 董秀琴^a, 张绪穆^b

a 武汉大学化学与分子科学学院生物医用高分子材料教育部重点实验室有机硅化合物及材料教育部工程中心武汉 430072;
b 南方科技大学化学系广东深圳 518055

收稿日期:2019-12-19 修回日期:2020-01-20 发布日期:2020-02-15
通讯作者: 董秀琴 E-mail:xiuqindong@whu.edu.cn
基金资助:
国家自然科学基金（No.21502145）、武汉市青年科技晨光计划（No.2017050300307）和江苏省自然科学基金（No.SBK2019041078）资助项目.

Recent Advances of Nickel-Catalyzed Homogeneous Asymmetric Hydrogenation

Liu Yuanhua^a, Dong Xiu-Qin^a, Zhang Xumu^b

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

Received:2019-12-19 Revised:2020-01-20 Published:2020-02-15
Supported by:
Project 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).

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.

Key words: asymmetric hydrogenation, nickel catalysis, chiral diphosphine ligand, chiral compounds, stereoselectivity

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
(b) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
(c) Minnaard, A. J.; Feringa, B. L.; Lefort, L.; de Vries, J. G. Acc. Chem. Res. 2007, 40, 1267.
(d) Zhang, W.; Chi, Y.; Zhang, X. Acc. Chem. Res. 2007, 40, 1278.
(e) Zhou, Y.-G. Acc. Chem. Res. 2007, 40, 1357.
(f) Roseblade, S. J.; Pfaltz, A. Acc. Chem. Res. 2007, 40, 1402.
(g) Xie, J. H.; Zhu, S. F.; Zhou, Q. L. Chem. Rev. 2011, 111, 1713.
(h) Wang, Y.; Zhang, Z.; Zhang, W. Chin. J. Org. Chem. 2015, 35, 528(in Chinese). (王英杰, 张振锋, 张万斌, 有机化学, 2015, 35, 528.)
(i) Wang, D.-S.; Chen, Q.-A.; Lu, S.-M.; Zhou, Y.-G. Chem. Rev. 2012, 112, 2557.
(j) Chen, Q.-A.; Ye, Z.-S.; Duan, Y.; Zhou, Y.-G. Chem. Soc. Rev. 2013, 42, 497.
(k) Verendel, J. J.; Pamies, O.; Dieguez, M.; Andersson, P. G. Chem. Rev. 2014, 114, 2130.
(l) Zhang, Z.; Butt, N. A.; Zhang, W. Chem. Rev. 2016, 116, 14769.
(m) de Vries, J. G.; Elsevier, C. J. Handbook of Homogeneous Hydrogenation, Wiley-VCH, Weinheim, Germany, 2007.
(n) Ma, Y.; Zhang, Y. J.; Zhang, W. Chin. J. Org. Chem. 2007, 27, 289(in Chinese). (马元辉, 张勇健, 张万斌, 有机化学, 2007, 27, 289.)
(o) Xie, J.-H.; Zhou, Q.-L. Acta Chim. Sinica 2012, 70, 1427(in Chinese). (谢建华, 周其林, 化学学报, 2012, 70, 1427.)
(p) Wang, Z.; Zhang, Z.; Liu, Y.; Zhang, W. Chin. J. Org. Chem. 2016, 36, 447(in Chinese). (王志惠, 张振锋, 刘燕刚, 张万斌, 有机化学, 2016, 36, 447.)
(q) Chen, S.; Yang, W.; Yao, Y.; Yang, X.; Deng, Y.; Yang, D. Chin. J. Org. Chem. 2018, 38, 2534(in Chinese). (陈姝琪, 杨文, 姚永祺, 杨新, 邓颖颍, 杨定乔, 有机化学, 2018, 38, 2534.)
(r) Liang, Z.; Yang, T.; Gu, G.; Dang, L.; Zhang, X. Chin. J. Chem. 2018, 36, 851.
[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] (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] 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.
[5] Hamada, Y.; Koseki, Y.; Fujii, T.; Maeda, T.; Hibino, T.; Makino, K. Chem. Commun. 2008, 6206.
[6] Hibino, T.; Makino, K.; Sugiyama, T.; Hamada, Y. ChemCatChem 2009, 1, 237.
[7] Dong, Z. R.; Li, Y. Y.; Yu, S. L.; Sun, G. S.; Gao, J. X. Chin. Chem. Lett. 2012, 23, 533.
[8] Corma, A.; Iglesias, M.; Del Pino, C.; Sanchez, F. J. Organomet. Chem. 1992, 431, 233.
[9] Yang, P.; Xu, H.; Zhou, J. Angew. Chem., Int. Ed. 2014, 53, 12210.
[10] Guo, S. Y.; Yang, P.; Zhou, J. Chem. Commun. 2015, 51, 12115.
[11] Guo, S.; Zhou, J. Org. Lett. 2016, 18, 5344.
[12] Gao, W.; Lv, H.; Zhang, T.; Yang, Y.; Chung, L. W.; Wu, Y.; Zhang, X. Chem. Sci. 2017, 8, 6419.
[13] Li, X.; You, C.; Li, S.; Lv, H.; Zhang, X. Org. Lett. 2017, 19, 5130.
[14] Long, J.; Gao, W.; Guan, Y.; Lv, H.; Zhang, X. Org. Lett. 2018, 20, 5914.
[15] Han, Z.; Liu, G.; Zhang, X.; Li, A.; Dong, X.-Q.; Zhang, X. Org. Lett. 2019, 21, 3923.
[16] Guan, Y.; Han, Z.; Li, X.; You, C.; Tan, X.; Lv, H.; Zhang, X. Chem. Sci. 2019, 10, 252.
[17] You, C.; Li, X.; Gong, Q.; Wen, J.; Zhang, X. J. Am. Chem. Soc. 2019, 141, 14560.
[18] Xu, H.; Yang, P.; Chuanprasit, P.; Hirao, H.; Zhou, J. Angew. Chem., Int. Ed. 2015, 54, 5112.
[19] Yang, P.; Lim, L. H.; Chuanprasit, P.; Hirao, H.; Zhou, J. Angew. Chem., Int. Ed. 2016, 55, 12083.
[20] Zhao, X.; Xu, H.; Huang, X.; Zhou, J. Angew. Chem., Int. Ed. 2019, 58, 292.
[21] Li, B.; Chen, J.; Zhang, Z.; Gridnev, I. D.; Zhang, W. Angew. Chem., Int. Ed. 2019, 58, 7329.
[22] Liu, Y.; Yi, Z.; Tan, X.; Dong, X.-Q.; Zhang, X. iScience 2019, 19, 63.
[23] Zhao, X.; Zhang, F.; Liu, K.; Zhang, X.; Lv, H. Org. Lett. 2019, 21, 8966.

镍催化均相不对称氢化反应研究进展

Recent Advances of Nickel-Catalyzed Homogeneous Asymmetric Hydrogenation

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Wanting Chen, Xiongwei Zhong, Jiale Xing, Changshu Wu, Yang Gao. Progress in Asymmetric Catalytic Synthesis of C—N Axis Chiral Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 349-377.
[2]	Quanbin Jiang. Progress in Synthesis of Axially Chiral Compounds through aza-Vinylidene o-Quinone Methide Intermediates [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 159-172.
[3]	Jingrui Wang, Yongkui Feng, Nengzhong Wang, Nianyu Huang, Hui Yao. Pd-Catalyzed Stereoselective Synthesis of Nitroalkyl β-C-Glycosides [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3216-3225.
[4]	Yangyang Chu, Zhaobin Han, Kuiling Ding. Progresses in the Application of Kinetic Resolution in Transition Metal Catalyzed Asymmetric (Transfer) Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1934-1951.
[5]	Xun Xiang, Zhaolin He, Xiuqin Dong. Recent Advances of Efficient Synthesis of Chiral Molecules Promoted by Pd/Chiral Phosphoric Acid Synergistic Catalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 791-808.
[6]	Yanyan Zhang, Zhuzhu Zhang, Shengqing Zhu, Lingling Chu. Recent Advances in Nickel Catalyzed Asymmetric Acylation Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1023-1035.
[7]	Licheng Wu, Xianqing Wu, Jingping Qu, Yifeng Chen. Exploration of Quinim Ligand in Ni-Catalyzed Enantioselective Reductive Carbamoyl-Alkylation of Alkene [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4239-4250.
[8]	Kang Pan, Fan Xu. Lanthanum Silylamide-Catalyzed Synthesis of Enol Phosphates [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4261-4267.
[9]	Yunpeng Qi, Dengkai Lin, Liang-An Chen. Research Progress on Reductive Acylation with Acyl-Ni as a Key Intermediate to Synthesize Ketones [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3861-3875.
[10]	Weilu Zhang, Shaowei Chen, Xiao Shen. Nickel-Catalyzed [4＋2] Cyclization of Benzosilacyclobutenes and Acylsilanes [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3635-3643.
[11]	Qi Sun, Zeying Sun, Ze Yu, Guangwei Wang. Nickel-Catalyzed Stereoselective Aryl-Difluoroalkylation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2515-2520.
[12]	Xueli Zhu, Shaoli Yang, Caixia Jia, Jing Li, Zheng Duan. Synthesis of Dihydrobenzooxaphospholes via Cyclocondensation of 2-Phosphinylphenol and Aldehydes [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2201-2213.
[13]	Mengnan Lai, Qiuyuan Wang, Min Hua, Nianyu Huang, Hui Yao. Open-Air Stereoselective Synthesis of C-Aryl Fucosides/Arabinosides [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1694-1705.
[14]	Weiguo Yu, Lingna Wang, Xiaocong Yu, Shuping Luo. Fluorescent Dye/Nickel Synergistic Catalytic Decarboxylative Carbonylation Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1216-1223.
[15]	Yurong Zhang, Han Wang, Yongjun Mao, Shiliang Shi. Ni-Catalyzed Three-Component Coupling Reaction of Butadiene,Aldimines and Alkenylboronic Acids [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1198-1209.