Recent Progress of Metal/Metal Oxide Nanoparticles for Asymmetric Hydrogenation and Transfer Hydrogenation

doi:10.6023/A14040325

Acta Chimica Sinica ›› 2014, Vol. 72 ›› Issue (7): 798-808.DOI: 10.6023/A14040325 Previous Articles Next Articles

Special Issue: 不对称催化与合成

Review

金属/金属氧化物纳米粒子在不对称氢化和氢转移反应中的应用研究进展

季益刚^a,c, 吴磊^a, 范青华^b

a 南京农业大学理学院化学系南京 210095;
b 中国科学院化学研究所分子识别与功能院重点实验室北京 100190;
c 江苏第二师范学院生命科学与化学化工学院南京 210013

投稿日期:2014-04-25 发布日期:2014-05-07
通讯作者: 吴磊, 范青华 E-mail:rickywu@njau.edu.cn;fanqh@iccas.ac.cn
基金资助:
项目受国家自然科学基金（Nos.21372118，21232008）、国家重点基础研究发展计划（No.2010CB833300）、江苏省“333高层次人才培养工程”、江苏省“青蓝工程”和南京农业大学中央高校基本科研业务费-引进人才专项资金（No.KYRC201211）资助.

Recent Progress of Metal/Metal Oxide Nanoparticles for Asymmetric Hydrogenation and Transfer Hydrogenation

Ji Yigang^a,c, Wu Lei^a, Fan Qinghua^b

a Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China;
b CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190, China;
c Department of Life Sciences and Chemistry, Jiangsu Second Normal University, Nanjing 210013, China

Received:2014-04-25 Published:2014-05-07
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21372118, 21232008), the National Basic Research Program of China(No. 2010CB833300), “333 High Level Talent Project”, “QingLan Project” of JiangSu Province and the Fundamental Research Funds for the Central Universities (NJAU) (No. KYRC201211).

Metal/metal oxide nanoparticles for asymmetric hydrogenation and transfer hydrogenation have emerged as a frontier and evolved into a hot topic of asymmetric catalysis in recent years. Their catalytic modes resemble that of “nano-reactor”, where substrates diffuse through organic shells into catalytic active sites. Thus, high local catalyst concentration usually dramatically improves TON and TOF. In the case of nanoparticles as active sites, Orito’s platinum catalytic system received most extensive interests. Achievements have been made in chiral modifier structural modification, catalyst supports, reaction medium, nanoparticle morphology and catalytic mechanism. Moreover, other metal nanoparticles including palladium, rhodium, ruthenium, iridium and iron exhibited favorable catalytic efficiency in the asymmetric hydrogenation and transfer hydrogenation of alkenes, ketones and imines, especially for iridium and iron nanoparticles, ee values over 95% were obtained. In another case of metal/metal oxide nanoparticles as catalyst supports, comparable efficiency and enantioselectivity were observed to homogeneous catalysts, meanwhile, this protocol overcame the drawbacks of homogeneous catalysts with easier recovery and reuse. This review presents a brief overview on the recent progress in the asymmetric hydrogenation and transfer hydrogenation catalyzed by metal/metal oxide nanoparticles, as well as the related catalytic mechanism. However, there are still many challenges in this promising research field of metal/metal oxide nanoparticles for asymmetric catalysis. In addition to the continuous understanding of the catalytic mechanism, it is highly desirable to develop new types of metal/metal oxide nanoparticles with high efficiency, high enantioselectivity, and convenient recyclability.

Key words: transition metal, metal nanoparticles, asymmetric hydrogenation, asymmetric transfer hydrogenation, catalyst recycling

Cite this article

Ji Yigang, Wu Lei, Fan Qinghua. Recent Progress of Metal/Metal Oxide Nanoparticles for Asymmetric Hydrogenation and Transfer Hydrogenation[J]. Acta Chimica Sinica, 2014, 72(7): 798-808.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.

(b) Xie, J. H.; Zhou, Q. L. Acta Chim. Sinica 2012, 70, 1427. (谢建华, 周其林, 化学学报, 2012, 70, 1427.)

(c) Wang, D.; Hou, C. J.; Chen, L.-F.; Liu, X. N.; An, Q. D.; Hu, X. P. Chin. J. Org. Chem. 2013, 33, 1355. (王东, 候传金, 陈丽凤, 刘小宁, 安庆大, 胡向平, 有机化学, 2013, 33, 1355.)

(d) Cui, P. L.; Liu, H. M.; Guo, X. M.; Zhang, D. N.; Wang, Y. E.; Wang, C. Chin. J. Org. Chem. 2013, 33, 436. (崔朋雷, 刘卉敏, 果秀敏, 张冬暖, 王彦恩, 王春, 有机化学, 2013, 33, 436.)

(e) Li, X. N.; Zhang, P. L.; Duan, K.; Wang, J. X. Chin. J. Org. Chem. 2012, 32, 19. (李小娜, 张鹏亮, 段凯, 王家喜, 有机化学, 2012, 32, 19.)

(f) Liu, Y.; Wang, Z.; Ding, K. L. Acta Chim. Sinica 2012, 70, 1464. (刘龑, 王正, 丁奎岭, 化学学报, 2012, 70, 1464.)

[2] Knowles, W. S. Acc. Chem. Res. 1983, 16, 106.

[3] (a) Fan, Q. H.; Li, Y. M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.

(b) Handbook of Asymmetric Heterogeneous Catalysis,Eds.: Ding, K.; Uozumi, Y., Wiley-VCH, 2008.

[4] (a) Wang, Z.; Chen, G.; Ding, K. L. Chem. Rev. 2009, 109, 322.

(b) Fan, Q. H.; Ding, K. L. Top. Organomet. Chem. 2011, 36, 207.

(c) Ma, B. D.; Deng, G. J.; Liu, J. ; He, Y. M.; Fan, Q. H. Acta Chim. Sinica 2013, 71, 528. (马保德, 邓国军, 刘继, 何艳梅, 范青华, 化学学报, 2013, 71, 528.)

(d) Liu, H. Q.; Shi, L.; Chen, Q. A.; Wang, L.; Zhou, Y. G. Acta Chim. Sinica 2013, 71, 40. (刘洪强, 时磊, 陈庆安, 王磊, 周永贵, 化学学报, 2013, 71, 40.)

[5] (a) Mallat, T.; Orglmeister, E.; Baiker, A. Chem. Rev. 2007, 107, 4863.

(b) Yasukawa, T.; Miyamura, H.; Kobayashi, S. Chem. Soc. Rev. 2014, 43, 1450.

[6] (a) Astruc, D.; Lu, F.; Aranzaes, J. R. Angew. Chem. Int. Ed. 2005, 44, 7852.

(b) Schätz, A.; Reiser, O.; Stark, W. J. Chem. Eur. J. 2010, 16, 8950.

[7] (a) Barbaro, P.; Santo, V. D.; Liguori, F. Dalton Trans. 2010, 39, 8391.

(b) Ranganath, K. V. S.; Glorius, F. Catal. Sci. Technol. 2011, 1, 13.

[8] Orito, Y.; Imai, S.; Niwa, S. Bull. Chem. Soc. Jpn. 1979, 1118.

[9] Harada, T.; Izumi, Y. Chem. Lett. 1978, 1195.

[10] Studer, M.; Blaser, H. U.; Exner, C. Adv. Synth. Catal. 2003, 345, 45.

[11] (a) Burgi, T.; Baiker, A. Acc. Chem. Res. 2004, 37, 909.

(b) Chen, C. H.; Zhan, E. S.; Li, Y.; Shen, W. J. J. Mol. Catal. A-Chem. 2013, 379, 117.

[12] (a) Griffiths, S. P.; Johnson, P.; Wells, P. B. Appl. Catal. A 2000, 191, 193.

(b) Chen, Z. J.; Li, X. H.; Li, C. Chin. J. Catal. 2011, 32, 155. (陈志坚, 李晓红, 李灿, 催化学报, 2011, 32, 155.)

[13] Li, X.; Shen, Y.; Xing, R.; Liu, Y. M.; Wu, H. H.; He, M. Y.; Wu, P. Catal. Lett. 2008, 122, 325.

[14] Xing, L.; Du, F.; Liang, J. J.; Chen, Y. S.; Zhou, Q. L. J. Mol. Catal. A-Chem. 2007, 276, 191.

[15] Li, B.; Li, X. H.; Wang, H. N.; Wu, P. J. Mol. Catal. A-Chem. 2011, 345, 81.

[16] Schmidt, E.; Vargas, A.; Mallat, T.; Baiker, A. J. Am. Chem. Soc. 2009, 131, 12358.

[17] Nandanan, E.; Gu, H. W.; Shao, H. L.; Jiang, J.; Ying, J. Y. Green Chem. 2011, 13, 3070.

[18] Beier, M. J.; Andanson, J.-M.; Mallat, T.; Krumeich, F.; Baiker, A. ACS Catal. 2012, 2, 337.

[19] Chen, Z. J.; Guan, Z. H.; Li, M. R.; Yang, Q. H.; Li, C. Angew. Chem. Int. Ed. 2011, 50, 4913.

[20] Guan, Z.; Lu, S.; Chen, Z.; Li, C.J. Catal. 2013, 305, 19.

[21] (a) Lavoie, S.; Mahieu, G.; McBreen, P. H. Angew. Chem. Int. Ed. 2006, 45, 7404.

(b) Lavoie, S.; Laliberté, M.-A.; Temprano, I.; McBreen, P. H. J. Am. Chem. Soc. 2006, 128, 7588.

[22] Schmidt, E.; Bucher, C.; Santarossa, G.; Mallat, T.; Gilmour, R.; Baiker, A. J. Catal. 2012, 289, 238.

[23] Meemken, F.; Maeda, N.; Hungerbühler, K.; Baiker, A. Angew. Chem. Int. Ed. 2012, 51, 8212.

[24] Perez, J. R. G.; Malthete, J.; Jacques, J. CR. Acad. Sc. Paris Serie Ⅱ . 1985, 300, 169.

[25] (a) Chen, C. H.; Zhan, E. S.; Li, Y.; Shen, W. J. Acta Chim. Sinica 2013, 71, 1505. (陈春辉, 展恩胜, 李勇, 申文杰, 化学学报, 2013, 71, 1505.)

(b) Chen, C. H.; Zhan, E. S.; Ta, N.; Li, Y.; Shen, W. J. Catal. Sci. Technol. 2013, 3, 2620.

[26] Huck, W.-R.; Mallat, T.; Baiker, A. New J. Chem. 2002, 26, 6.

[27] Nitta, Y.; Watanabe, J.; Okuyama, T.; Sugimura, T. J. Catal. 2005, 236, 164.

[28] Makra, Z.; Szöllösi, G.; Bartók, M. Catal. Today 2012, 181, 56.

[29] Maris, M.; Huck, W.-R.; Mallat, T.; Baiker, A. J. Catal. 2003, 219, 52.

[30] Watson, D. J.; Jesudason, R. J.; Beaumont, S. K.; Kyriakou, G.; Burton, J. W.; Lambert, R. M. J. Am. Chem. Soc. 2009, 131, 14584.

[31] Ma, H.; Chen, H.; Zhang, Q.; Li, X. J. Mol. Catal. A-Chem. 2003, 196, 131.

[32] Sonderegger, O. J.; Ho, G. M.-W.; Bürgi, T.; Baiker, A. J. Catal. 2005, 230, 499.

[33] Wang, J.; Feng, J.; Qin, R.; Fu, H.; Yuan, M.; Chen, H.; Li, X. Tetrahedron: Asymmetry 2007, 18, 1643.

[34] Jiang, H. Y.; Yang, C. F.; Li, C.; Fu, H. Y.; Chen, H.; Li, R. X.; Li, X. J. Angew. Chem. Int. Ed. 2008, 47, 1.

[35] Jiang, H. Y.; Sun, B.; Zheng, X. X.; Chen, H. Appl. Catal. A- Gen. 2012, 421, 86.

[36] (a) Johnson, N. B.; Lennon, I. C.; Moran, P. H.; Ramsden, J. A. Acc. Chem. Res. 2007, 40, 1291.

(b) Sun, Q.; Meng, X. J.; Liu, X.; Zhang, X. M.; Yang, Y.; Yang, Q. H.; Xiao, F. S. Chem. Commun. 2012, 48, 10505.

[37] Groves, J. T.; Myers, R. S. J. Am. Chem. Soc. 1983, 105, 5791.

[38] Gopalaiah, K. Chem. Rev. 2013, 113, 3248.

[39] (a) Mikhailine, A.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2009, 131, 13943.

(b) Sonnenberg, J. F.; Coombs, N.; Dube, P. A.; Morris, R. H. J. Am. Chem. Soc. 2012, 134, 5893.

[40] Li, Y. Y.; Yu, S.; Wu, X.; Xiao, J.; Shen, W. Y.; Dong, Z. R.; Gao, J. X. J. Am. Chem. Soc. 2014, 136, 4031.

[41] Wu, L. Ph.D. Dissertation, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing, 2007. (吴磊, 博士论文, 中国科学院化学研究所, 北京, 2007.)

[42] Li, H.; Luk, Y. Y.; Mrksich, M. Langmuir 1999, 15, 4957.

[43] Daniel, M. C.; Astruc, D. Chem. Rev. 2004, 104, 293.

[44] Belser, T.; Stöhr, M.; Pfaltz, A. J. Am. Chem. Soc. 2005, 127, 8720.

[45] Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H.; Bouhrara, M.; Basset, J. M. Chem. Rev. 2011, 111, 3036.

[46] Hu, A. G.; Yee, G. T.; Lin, W. B. J. Am. Chem. Soc. 2005, 127, 12486.

[47] Hu, A. G.; Liu, S.; Lin, W. B. RSC Adv. 2012, 2, 2576.

[48] Gao, X.; Liu, R.; Zhang, D.; Wu, M.; Cheng, T.; Liu, G. Chem. Eur. J. 2014, 20, 1515.

[49] Fraile, J. M.; García, J. I.; Mayoral, J. A. Chem. Rev. 2009, 109, 360.

[50] Wu, L.; He, Y. M.; Fan, Q. H. Adv. Synth. Catal. 2011, 353, 2915.

[51] Gleeson, O.; Davies, G. L.; Peschiulli, A.; Tekoriute, R.; Gun'ko, Y. K.; Connon, S. J. Org. Biomol. Chem. 2011, 9, 7929.

金属/金属氧化物纳米粒子在不对称氢化和氢转移反应中的应用研究进展

Recent Progress of Metal/Metal Oxide Nanoparticles for Asymmetric Hydrogenation and Transfer Hydrogenation

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Xinhong Cai, Jianzhong Chen, Wanbin Zhang. Development of Construction of Chiral C—X Bonds through Nickel Catalyzed Asymmetric Hydrogenation^★ [J]. Acta Chimica Sinica, 2023, 81(6): 646-656.
[2]	Huang Jiapian, Liu Fei, Wu Jie. Recent Advances in the Transformation of Difluorocyclopropenes^★ [J]. Acta Chimica Sinica, 2023, 81(5): 520-532.
[3]	Xuelu Ma, Meng Li, Ming Lei. Trinuclear Transition Metal Complexes in Catalytic Reactions [J]. Acta Chimica Sinica, 2023, 81(1): 84-99.
[4]	Xia Liu, Chunxiang Kuang, Changhui Su. Transition-metal Catalyzed 1,2,3-Triazole-assisted C—H Functionalization Processes [J]. Acta Chimica Sinica, 2022, 80(8): 1135-1151.
[5]	Yang, Qi-Liang, Wang, Xiang-Yang, Weng, Xin-Jun, Yang, Xiang, Xu, Xue-Tao, Tong, Xiaofeng, Fang, Ping, Wu, Xin-Yan, Mei, Tian-Sheng. Palladium-Catalyzed ortho-Selective C—H Chlorination of Arenes Using Anodic Oxidation [J]. Acta Chimica Sinica, 2019, 77(9): 866-873.
[6]	Zhang, Hong-Hao, Yu, Shouyun. Advances on Transition Metals and Photoredox Cooperatively Catalyzed Allylic Substitutions [J]. Acta Chimica Sinica, 2019, 77(9): 832-840.
[7]	Lu, Fu-Dong, Jiang, Xuan, Lu, Liang-Qiu, Xiao, Wen-Jing. Application of Propargylic Radicals in Organic Synthesis [J]. Acta Chimica Sinica, 2019, 77(9): 803-813.
[8]	Wang Qiang, Gu Qing, You Shu-Li. Recent Progress on Transition-Metal-Catalyzed Asymmetric C-H Bond Functionalization for the Synthesis of Biaryl Atropisomers [J]. Acta Chim. Sinica, 2019, 77(8): 690-704.
[9]	Li Cui, Zhang Qi, Fu Yao. Transition Metal Catalyzed Deoxydehydration of Alcohols [J]. Acta Chim. Sinica, 2018, 76(7): 501-514.
[10]	Li Pan, Liu Jian, Sun Weiyi, Tao Zhanliang, Chen Jun. Synthesis of Coin-like Vanadium Disulfide and Its Sodium Storage Performance [J]. Acta Chim. Sinica, 2018, 76(4): 286-291.
[11]	Hu Shu-Boa, Chen Mu-Wang, Zhai Xiao-Yong, Zhou Yong-Gui. Synthesis of Tetrahydropyrrolo/indolo[1,2-a]pyrazines by Enantioselective Hydrogenation of Heterocyclic Imines [J]. Acta Chim. Sinica, 2018, 76(2): 103-106.
[12]	Zhou Qiang, Lu Ping. Recent Advances in Cooperative Catalysis of Chiral Lewis Base and Transition Metal Catalyst [J]. Acta Chim. Sinica, 2018, 76(11): 825-830.
[13]	Zhang Mao-Mao, Luo Yuan-Yuan, Lu Liang-Qiu, Xiao Wen-Jing. Advances on Asymmetric Allylic Substitutions under Synergetic Catalysis System with Transition Metals and Organocatalysts [J]. Acta Chim. Sinica, 2018, 76(11): 838-849.
[14]	Li Jiapeng, Yin Jianhao, Yu Chao, Zhang Wenxiong, Xi Zhenfeng. Direct Transformation of N₂ to N-Containing Organic Compounds [J]. Acta Chim. Sinica, 2017, 75(8): 733-743.
[15]	Li Tiantian, Zhao Jikuan, Li Yao, Quan Zhenlan, Xu Jie. Synthesis and Electrochemical Properties of Nitrogen-Doped Partially Graphitized Carbon/Cobalt Iron Oxides Composite [J]. Acta Chim. Sinica, 2017, 75(5): 485-493.