Citation: Xu Huiting, Zhang Chaohuai, Chen Gang, Shen Runpu, Ying Anguo. Application of Task-Specific Ionic liquids to Organic Synthesis[J]. Chinese Journal of Organic Chemistry, ;2016, 36(10): 2353-2367. doi: 10.6023/cjoc201604053 shu

Application of Task-Specific Ionic liquids to Organic Synthesis

Xu Huiting ^a ,
Zhang Chaohuai ^b ,
Chen Gang ^b ,
Shen Runpu ^a,*,, ,
Ying Anguo ^b,*,,

a.
School of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing 312000
b.
School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 318000

Corresponding author: Shen Runpu, srunpu@usx.edu.cn Ying Anguo, yinganguo@163.com
Received Date: 26 April 2016
Revised Date: 28 May 2016

Fund Project: the National Natural Science Foundation of China Nos.21576176，21106090and the Science and Technology Innovation Undergraduate Program of Zhejiang Province No.2015R430015Project supported by the Natural Science Foundation of Zhejiang Province No.LY15B060002

Figures(12)

Ionic liquids (ILs) have been widely used as green reaction solvents and/or catalysts in organic synthesis due to their advantages, including low volatility, good thermal stability, good solubility and recyclability. ILs have played a significant role in accelerating reaction rate and selectivity. The recent advances in the application of ILs as catalysts or solvents are summarized in this review, such as in Baylis-Hillman reaction, Michael addition, oxidation and reduction reaction, Knoevenagel condensation, aldol reaction, Diels-Alder reaction, Heck coupling reaction, Suzuki reaction, asymmetric reaction, Biginelli reaction, Mannich reaction and Hantzsch reaction. Relationship between structure and catalytic efficiency of ILs as well as plausible mechanism has been discussed, which is beneficial to develop the novel task-specific ionic liquids with diverse functionalities.
- task-specific ionic liquids,
- organic synthesis,
- relationship between structure and activity,
- green chemistry,
- recy-clability
1. [1]
2. [2]
  Rogers, R. D. Nature 2007, 447, 917.
3. [3]
  Poulimenoua, N. I.; Giannopouloua, I.; Paniasa, D. Mater. Manuf. Process 2015, 30, 1403.
4. [4]
  Qureshi, Z. S.; Deshmukh, K. M.; Bhanage, B. M. Clean. Technol. Environ. Policy 2014, 16, 1487.
5. [5]
  Yang, J. B.; Zhou, L. H.; Guo, X. T.; Li, L. Chem. Eng. J. 2015, 280, 147.
6. [6]
  Zhou, Y.; Huang, W.; Chen, X. S.; Song, Z. B.; Tao, D. J. Catal. Lett. 2015, 145, 1830.
7. [7]
  Ali, E.; Alnashef, I.; Ajbar, A.; Mulyono, S.; Hizaddin, H. F.; Hadj-Kali, M. K. Korean J. Chem. Eng. 2013, 30, 2068.
8. [8]
9. [9]
  Benzagouta, M. S.; AlNashef, I. M.; Karnanda, W.; Al-Khidir, K. Korean J. Chem. Eng. 2013, 30, 2108.
10. [10]
  Mai, N. L.; Kim, S. H.; Ha, S. H.; Shin, H. S.; Koo, Y. M. Korean J. Chem. Eng. 2013, 30, 1804.
11. [11]
  Tseng, M. C.; Liang, Y. M.; Chu, Y. H. Tetrahedron Lett. 2005, 46, 6131.
12. [12]
  Zang, H. H.; Zhang, Y.; Cheng, B. W.; Zhang, W. W.; Xu, X. L.; Ren, Y. L. Chin. J. Chem. 2012, 30, 362.
13. [13]
14. [14]
  Popescu, A. M.; Constantin, V. Chem. Res. Chin. Univ. 2014, 30, 119.
15. [15]
  Vander, H. T.; Wellens, S.; Verachtert, K.; Binnemans, K. Green Chem. 2013, 15, 919. (b) Clark, K. D.; Nacham, O.; Yu, H. L.; Li, T. H.; Yamsek, M. M.; Ronning, D. R.; Anderson, J. L. Anal. Chem. 2015, 87, 1552.
16. [16]
  Abbott, A. P.; Frisch, G.; Gurman, S. J.; Hillman, A. R.; Hartley, J.; Holyoak, F.; Ryder, K. S. Chem. Commun. 2011, 47, 10031.
17. [17]
  Tschan, M. J. L.; Dieboh, O.; Leeuwen, P. W. N. M. Top. Cata1. 2014, 57, 1054.
18. [18]
  Oh, Y.; Hu, X. L. Chem. Commun. 2015, 51, 13698.
19. [19]
  Gallardo, I.; Vila, N. J. Org. Chem. 2010, 75, 680.
20. [20]
  Hsieh, Y. T.; Sun, I. W. Chem. Commun. 2014, 50, 246.
21. [21]
  Armand, M.; Endres, F.; Macfarlane, D. R.; Ohno, H.; Scrosati, B. Nat. Mater. 2009, 8, 621.
22. [22]
  Wang, C. F.; Chen, Y. J.; Zhuo, K. L. Chem. Commun. 2013, 49, 3336.
23. [23]
24. [24]
25. [25]
26. [26]
  Basavaiah, D.; Dharma, R. P.; Suguna, H. R. Tetrahedron 1996, 52, 8001. (b) Basaviah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
27. [27]
  Zhao, S. H.; Zhang, Q. J.; Duan, X. E. Synth. Commun. 2011, 41, 3289.
28. [28]
29. [29]
  Song, Y.; Ke, H. H.; Wang, N.; Wang, L. M.; Zou, G. Tetrahedron 2009, 65, 9086.
30. [30]
  Lenardão, E. J.; Feijó, J. O.; Thurow, Samuel.; Perin, G.; Jacob, R. G.; Silveira, C. C. Tetrahedron Lett. 2009, 50, 5215.
31. [31]
  Keithellakpam, S.; Laitonjam, W. S. Chin. Chem. Lett. 2014, 25, 767.
32. [32]
  Chelghoum, M.; Bahnous, M.; Bouraiou, A.; Bouacida, S.; Belfaitah, A. Tetrahedron Lett. 2012, 53, 4059.
33. [33]
  Ying, A. G.; Li, Z. F.; Yang, J. G.; Liu, S.; Xu, S. L.; Yan, H.; Wu, C. L. J. Org. Chem. 2014, 79, 6510.
34. [34]
  Hou, H. L.; Qiu, F. L.; Ying, A. G.; Xu, S. L. Chin. Chem. Lett. 2015, 26, 377.
35. [35]
  Du, Z. Y.; Ng, H. F.; Zhang, K.; Zeng, H. Q.; Wang, J. Org. Biomol. Chem. 2011, 9, 6930.
36. [36]
  Van, Doorslaer. C.; Schellekens, Y.; Mertens, P.; Binnemansb, K.; De, Vos. D. Phys. Chem. Chem. Phys. 2010, 10, 1741.
37. [37]
  Sun, W. Y.; Ueyama, N.; Nakamura, A. Tetrahedron 1993, 49, 1357.
38. [38]
  Nishiguchi, T.; Asano, F. J. Org. Chem. 1989, 54, 1531.
39. [39]
  Sahiner, N.; Sagbas, S.; Nahit, A. RSC Adv. 2015, 5, 18183.
40. [40]
  Das, J.; Velusamy, P. J. Taiwan Inst. Chem. Eng. 2014, 45, 2280.
41. [41]
  Sahiner, N.; Kaynak, A.; Butun, S. J. Non-Cryst. Solids 2012, 358, 758.
42. [42]
  Chauhan, M. S.; Singh, S. J. Mol. Catal. A:Chem. 2015, 398, 184.
43. [43]
  Chinnappan, A.; Kim, H. RSC. Adv. 2013, 3, 3399.
44. [44]
  Freeman, F. Chem. Rev. 1980, 80, 329.
45. [45]
  Tietze, L. F. Chem. Rev. 1996, 96, 115.
46. [46]
  Rumer, J. W.; Levick, M.; Dai, S. Y.; Rossbauer, S.; Huang, Z. G.; Biniek. L.; Anthopoulos, T. D.; Durrant, J. R.; Procter, D. J.; McCulloch, I. Chem. Commun. 2013, 49, 4465.
47. [47]
  Liang, F.; Pu, Y. J.; Kurata, T.; Kido, J.; Nishide, H. Polymer 2005, 46, 3767.
48. [48]
  Zahouily, M.; Salah, M.; Bahlaouane, B.; Rayadh, A.; Houmam, A.; Hamed, E. A.; Sebti, S. Tetrahedron 2004, 60, 1631.
49. [49]
  Ouyang, F.; Zhou, Y.; Li, Z M.; Hu, N.; Tao, D. J. Korean J. Chem. Eng. 2014, 31, 1377.
50. [50]
  Bahrami, K.; Khodaei, M. M.; Babajani N.; Naali, F. J. Iran. Chem. Soc. 2014, 11, 1675.
51. [51]
  Ding, L. B.; Li, H. S.; Zhang, Y. P.; Zhang, K.; Yuan, H.; Wu, Q.; Zhao, Y.; Jiao, Q. Z.; Shi, D. X. RSC Adv. 2015, 5, 21415.
52. [52]
  Ying, A. G.; Ni, Y. X.; Xu, S. L.; Liu, S.; Yang, J. G.; Li, R. R. Ind. Eng. Chem. Res. 2014, 53, 5678.
53. [53]
54. [54]
  Davoodnia, A.; Yassaghi, G. Chin. J. Catal. 2012, 33, 1950.
55. [55]
  Iglesias, M.; Gonzalez-Olmos, R.; Cota, I.; Medina, F. Chem. Eng. J. 2010, 162, 802.
56. [56]
  Wang, C.; Liu, J.; Leng, W. G.; Gao, Y. N. Int. J. Mol. Sci. 2014, 15, 1284.
57. [57]
58. [58]
  Ying, A. G.; Xu, S. L.; Liu, Shuo.; Ni, Y. X.; Yang, J. G.; Wu, C. L. Ind. Eng. Chem. Res. 2014, 53, 547.
59. [59]
  Erfurt, K.; Wandzik, I.; Walczak, K.; Matuszek, K.; Chrobok, A. Green Chem. 2014, 16, 3508.
60. [60]
  Zhu, X. Y.; Liu, J. Q.; Zhang, D. G.; Liu, C. B. Comput. Theor. Chem. 2012, 996, 21.
61. [61]
  Wang, Y. P.; Lee, H. M. J. Org. Chem. 2015, 791, 90.
62. [62]
  Nowrouzia, N.; Tarokha, D.; Motevalli, S. J. Mol. Catal. A:Chem. 2014, 385, 13.
63. [63]
64. [64]
  Wang, M.; Yuan, X. B.; Li, H. Y.; Ren, L. M.; Sun, Z. Z.; Hou, Y. J.; Chu, W. Y. Catal. Commun. 2015, 58, 154.
65. [65]
  Boruah, P. R.; Koiri, M. J.; Bora, U.; Sarma, D. Tetrahedron Lett. 2014, 55, 2423.
66. [66]
  Xu, D.; Zhou, Z. M.; Da, L.; Tang, L. W.; Zhang, J. Bioorg. Med. Chem. Lett. 2015, 25, 1961.
67. [67]
  Kaur, A.; Singh, V. Synlett 2014, 1191.
68. [68]
  Liu, X. R.; Chen, C.; Xiu, Y. H.; Chen, A. J.; Guo, L.; Zhang, R.; Chen, J. Z.; Hou, Z. S. Catal. Commun. 2015, 67, 90.
69. [69]
  Shaterian, H. R.; Aghakhanizadeh, M. Phosphorus, Sulfur Silicon Relat. Elem. 2013, 188, 1064.
70. [70]
  Fang, D.; Zhang, D. Z.; Liu, Zu. L. Monatsh. Chem. 2010, 141, 419.
71. [71]
  He, L. Q.; Qin, S. J.; Chang, T.; Sun, Y. Z.; Zhao, J. Q. Int. J. Mol. Sci. 2014, 15, 8656.
72. [72]
  Nagarajan, S.; Kandasamy, E. Catal. Lett. 2014, 144, 1507.
73. [73]
  Dayanand, P.; Dattatray, C.; Abhijeet, M. Catal. Lett. 2014, 144, 949.
74. [74]
  Heravi, M. M.; Saeedi, M.; Karimi, N.; Zakeri, M.; Beheshtiha, Y. S.; Davoodnia, A. Synth. Commun. 2010, 40, 523.
75. [75]
  Ying, A. G.; Liu, S.; Yang, J. G.; Hu, H. N. Ind. Eng. Chem. Res. 2014, 53, 16143.
1. [1]
  Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
2. [2]
  Fengxiao Wang , Zhiwei Miao , Yaofeng Yuan . 有机磷化学与化学教学. University Chemistry, 2025, 40(8): 158-168. doi: 10.12461/PKU.DXHX202410077
3. [3]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
4. [4]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044
5. [5]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
6. [6]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
7. [7]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
8. [8]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
9. [9]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
10. [10]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
11. [11]
  Haiying Jiang , Liuhong Song , Yangyang Cheng , Kefen Yue , Mingli Peng , Huilin Guo . Ph―C≡C―Cu_2.5的力致变色现象探究——推荐一个物理化学实验. University Chemistry, 2025, 40(8): 249-254. doi: 10.12461/PKU.DXHX202410003
12. [12]
  Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
13. [13]
  Zhilian Liu , Wengui Wang , Hongxiao Yang , Yu Cui , Shoufeng Wang . Ideological and Political Education Design for the Synthesis of Irinotecan Drug Intermediate 7-Ethyl Camptothecin. University Chemistry, 2024, 39(2): 89-93. doi: 10.3866/PKU.DXHX202306012
14. [14]
  Zijian Zhao , Yanxin Shi , Shicheng Li , Wenhong Ruan , Fang Zhu , Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094
15. [15]
  Jihua Deng , Xinshi Wu , Dichang Zhong . Exploration of Green Teaching and Ideological and Political Education in Chemical Experiment of “Preparation of Ammonium Ferrous Sulfate”. University Chemistry, 2024, 39(10): 325-329. doi: 10.12461/PKU.DXHX202405046
16. [16]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
17. [17]
  Yifan Liu , Haonan Peng . AI-Assisted New Era in Chemistry: A Review of the Application and Development of Artificial Intelligence in Chemistry. University Chemistry, 2025, 40(7): 189-199. doi: 10.12461/PKU.DXHX202405182
18. [18]
  Xue Dong , Xiaofu Sun , Shuaiqiang Jia , Shitao Han , Dawei Zhou , Ting Yao , Min Wang , Minghui Fang , Haihong Wu , Buxing Han . Electrochemical CO₂ Reduction to C₂₊ Products with Ampere-Level Current on Carbon-Modified Copper Catalysts. Acta Physico-Chimica Sinica, 2025, 41(3): 2404012-0. doi: 10.3866/PKU.WHXB202404012
19. [19]
  Yunchao Li , Shanying Chen , Ke Qi , Kangning Huo , Shuxin Li , Jingyi Li , Ying Wei , Louzhen Fan . A New Colloid Electrophoresis Experiment Incorporating Characteristics of Inquiry Learning and Ideological and Political Education. University Chemistry, 2024, 39(2): 47-51. doi: 10.3866/PKU.DXHX202308063
20. [20]
  Ruizhi Duan , Xiaomei Wang , Panwang Zhou , Yang Liu , Can Li . The role of hydroxyl species in the alkaline hydrogen evolution reaction over transition metal surfaces. Acta Physico-Chimica Sinica, 2025, 41(9): 100111-0. doi: 10.1016/j.actphy.2025.100111

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(4624)
HTML views(388)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142