Chinese Journal of Organic Chemistry >
Application of Task-Specific Ionic liquids to Organic Synthesis
Received date: 2016-04-26
Revised date: 2016-05-28
Online published: 2016-06-08
Supported by
Project supported by the Natural Science Foundation of Zhejiang Province (No.LY15B060002), the National Natural Science Foundation of China (Nos.21576176, 21106090), and the Science and Technology Innovation Undergraduate Program of Zhejiang Province (No.2015R430015).
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.
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
[1] Yi, F. P.; Zhang, X.; Sun, H. Y.; Chen, S. H. Acta Chim. Sinica 2012, 70, 741(in Chinese). (易封萍, 张旋, 孙海洋, 陈世洪, 化学学报, 2012, 70, 741.)
[2] Rogers, R. D. Nature 2007, 447, 917.
[3] Poulimenoua, N. I.; Giannopouloua, I.; Paniasa, D. Mater. Manuf. Process 2015, 30, 1403.
[4] Qureshi, Z. S.; Deshmukh, K. M.; Bhanage, B. M. Clean. Technol. Environ. Policy 2014, 16, 1487.
[5] Yang, J. B.; Zhou, L. H.; Guo, X. T.; Li, L. Chem. Eng. J. 2015, 280, 147.
[6] Zhou, Y.; Huang, W.; Chen, X. S.; Song, Z. B.; Tao, D. J. Catal. Lett. 2015, 145, 1830.
[7] Ali, E.; Alnashef, I.; Ajbar, A.; Mulyono, S.; Hizaddin, H. F.; Hadj-Kali, M. K. Korean J. Chem. Eng. 2013, 30, 2068.
[8] Xu, S. Y.; Zhang, F. X.; Li, J. Y.; Bai, Y.; Xiao, W. J.; Peng, J. J. Prog. Chem. 2015, 27, 1400(in Chinese). (徐艺凇, 张凤香, 厉嘉云, 白赢, 肖文军, 彭家建, 化学进展, 2015, 27, 1400.)
[9] Benzagouta, M. S.; AlNashef, I. M.; Karnanda, W.; Al-Khidir, K. Korean J. Chem. Eng. 2013, 30, 2108.
[10] Mai, N. L.; Kim, S. H.; Ha, S. H.; Shin, H. S.; Koo, Y. M. Korean J. Chem. Eng. 2013, 30, 1804.
[11] Tseng, M. C.; Liang, Y. M.; Chu, Y. H. Tetrahedron Lett. 2005, 46, 6131.
[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] Ma, Y. Q.; Wang, R. Chem. J. Chin. Univ. 2013, 35, 760(in Chinese). (马云倩, 王睿, 高等学校化学学报, 2013, 35, 760.)
[14] Popescu, A. M.; Constantin, V. Chem. Res. Chin. Univ. 2014, 30, 119.
[15] (a) 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] Abbott, A. P.; Frisch, G.; Gurman, S. J.; Hillman, A. R.; Hartley, J.; Holyoak, F.; Ryder, K. S. Chem. Commun. 2011, 47, 10031.
[17] Tschan, M. J. L.; Dieboh, O.; Leeuwen, P. W. N. M. Top. Cata1. 2014, 57, 1054.
[18] Oh, Y.; Hu, X. L. Chem. Commun. 2015, 51, 13698.
[19] Gallardo, I.; Vila, N. J. Org. Chem. 2010, 75, 680.
[20] Hsieh, Y. T.; Sun, I. W. Chem. Commun. 2014, 50, 246.
[21] Armand, M.; Endres, F.; Macfarlane, D. R.; Ohno, H.; Scrosati, B. Nat. Mater. 2009, 8, 621.
[22] Wang, C. F.; Chen, Y. J.; Zhuo, K. L. Chem. Commun. 2013, 49, 3336.
[23] Hou, H. L.; Li, Z. F.; Ying, A. G.; Xu, S. L. Chin. J. Org. Chem. 2014, 34, 1277(in Chinese). (侯海亮, 李志峰, 应安国, 许松林, 有机化学, 2014, 34, 1277.)
[24] Hou, H. L.; Li, Z. F.; Ying, A. G.; Xu, S. L. Chin. J. Org. Chem. 2014, 34, 1074(in Chinese). (李志峰, 侯海亮, 应安国, 许松林, 有机化学, 2014, 34, 1074.)
[25] Pan, L. Y.; Li, Z. F.; Ni, Y. X.; Yao, Z. G.; Yu, Z. P.; Wu, W. K.; Ying, A. G. Chem. J. Chin. Univ. 2015, 36, 81(in Chinese). (泮丽亚, 李志峰, 倪宇翔, 姚振刚, 余志平, 吴文康, 应安国, 高等学校化学学报, 2015, 36, 81.)
[26] (a) 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] Zhao, S. H.; Zhang, Q. J.; Duan, X. E. Synth. Commun. 2011, 41, 3289.
[28] Zhao, S. H.; Wang, D.; Wang, M.; Kang, J.; Zhang, L. W.; Chin. J. Org. Chem. 2015, 35, 865(in Chinese). (赵三虎, 王豆, 王敏, 康锦, 张立伟. 有机化学, 2015, 35, 865.)
[29] Song, Y.; Ke, H. H.; Wang, N.; Wang, L. M.; Zou, G. Tetrahedron 2009, 65, 9086.
[30] Lenardão, E. J.; Feijó, J. O.; Thurow, Samuel.; Perin, G.; Jacob, R. G.; Silveira, C. C. Tetrahedron Lett. 2009, 50, 5215.
[31] Keithellakpam, S.; Laitonjam, W. S. Chin. Chem. Lett. 2014, 25, 767.
[32] Chelghoum, M.; Bahnous, M.; Bouraiou, A.; Bouacida, S.; Belfaitah, A. Tetrahedron Lett. 2012, 53, 4059.
[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] Hou, H. L.; Qiu, F. L.; Ying, A. G.; Xu, S. L. Chin. Chem. Lett. 2015, 26, 377.
[35] Du, Z. Y.; Ng, H. F.; Zhang, K.; Zeng, H. Q.; Wang, J. Org. Biomol. Chem. 2011, 9, 6930.
[36] Van, Doorslaer. C.; Schellekens, Y.; Mertens, P.; Binnemansb, K.; De, Vos. D. Phys. Chem. Chem. Phys. 2010, 10, 1741.
[37] Sun, W. Y.; Ueyama, N.; Nakamura, A. Tetrahedron 1993, 49, 1357.
[38] Nishiguchi, T.; Asano, F. J. Org. Chem. 1989, 54, 1531.
[39] Sahiner, N.; Sagbas, S.; Nahit, A. RSC Adv. 2015, 5, 18183.
[40] Das, J.; Velusamy, P. J. Taiwan Inst. Chem. Eng. 2014, 45, 2280.
[41] Sahiner, N.; Kaynak, A.; Butun, S. J. Non-Cryst. Solids 2012, 358, 758.
[42] Chauhan, M. S.; Singh, S. J. Mol. Catal. A:Chem. 2015, 398, 184.
[43] Chinnappan, A.; Kim, H. RSC. Adv. 2013, 3, 3399.
[44] Freeman, F. Chem. Rev. 1980, 80, 329.
[45] Tietze, L. F. Chem. Rev. 1996, 96, 115.
[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] Liang, F.; Pu, Y. J.; Kurata, T.; Kido, J.; Nishide, H. Polymer 2005, 46, 3767.
[48] Zahouily, M.; Salah, M.; Bahlaouane, B.; Rayadh, A.; Houmam, A.; Hamed, E. A.; Sebti, S. Tetrahedron 2004, 60, 1631.
[49] Ouyang, F.; Zhou, Y.; Li, Z M.; Hu, N.; Tao, D. J. Korean J. Chem. Eng. 2014, 31, 1377.
[50] Bahrami, K.; Khodaei, M. M.; Babajani N.; Naali, F. J. Iran. Chem. Soc. 2014, 11, 1675.
[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] 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] Liu, Y. T.; Li, R.; Xing, Y. J. Chin. J. Org. Chem. 2015, 35, 1520(in Chinese). (刘玉婷, 李戎, 邢彦军, 有机化学, 2015, 35, 1520.)
[54] Davoodnia, A.; Yassaghi, G. Chin. J. Catal. 2012, 33, 1950.
[55] Iglesias, M.; Gonzalez-Olmos, R.; Cota, I.; Medina, F. Chem. Eng. J. 2010, 162, 802.
[56] Wang, C.; Liu, J.; Leng, W. G.; Gao, Y. N. Int. J. Mol. Sci. 2014, 15, 1284.
[57] Cui, W. H.; Zhang, Y. M.; Jia, R. Y.; Wang, Y.; Wei, T. B. Chin. J. Org. Chem. 2015, 35, 890(in Chinese). (崔文辉, 张有明, 贾如琰, 王昱, 魏太保, 有机化学, 2015, 35, 890.)
[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] Erfurt, K.; Wandzik, I.; Walczak, K.; Matuszek, K.; Chrobok, A. Green Chem. 2014, 16, 3508.
[60] Zhu, X. Y.; Liu, J. Q.; Zhang, D. G.; Liu, C. B. Comput. Theor. Chem. 2012, 996, 21.
[61] Wang, Y. P.; Lee, H. M. J. Org. Chem. 2015, 791, 90.
[62] Nowrouzia, N.; Tarokha, D.; Motevalli, S. J. Mol. Catal. A:Chem. 2014, 385, 13.
[63] Yang, S. R.; Ling, G. W.; Ma, J. Y.; Zhang, L.; Li, J. X.; Luo, W. Chin. J. Org. Chem. 2014, 34, 1148(in Chinese). (杨少容, 凌厂围, 马建业, 张蕾, 李建晓, 罗维, 有机化学, 2014, 34, 1148.)
[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] Boruah, P. R.; Koiri, M. J.; Bora, U.; Sarma, D. Tetrahedron Lett. 2014, 55, 2423.
[66] Xu, D.; Zhou, Z. M.; Da, L.; Tang, L. W.; Zhang, J. Bioorg. Med. Chem. Lett. 2015, 25, 1961.
[67] Kaur, A.; Singh, V. Synlett 2014, 1191.
[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] Shaterian, H. R.; Aghakhanizadeh, M. Phosphorus, Sulfur Silicon Relat. Elem. 2013, 188, 1064.
[70] Fang, D.; Zhang, D. Z.; Liu, Zu. L. Monatsh. Chem. 2010, 141, 419.
[71] He, L. Q.; Qin, S. J.; Chang, T.; Sun, Y. Z.; Zhao, J. Q. Int. J. Mol. Sci. 2014, 15, 8656.
[72] Nagarajan, S.; Kandasamy, E. Catal. Lett. 2014, 144, 1507.
[73] Dayanand, P.; Dattatray, C.; Abhijeet, M. Catal. Lett. 2014, 144, 949.
[74] Heravi, M. M.; Saeedi, M.; Karimi, N.; Zakeri, M.; Beheshtiha, Y. S.; Davoodnia, A. Synth. Commun. 2010, 40, 523.
[75] Ying, A. G.; Liu, S.; Yang, J. G.; Hu, H. N. Ind. Eng. Chem. Res. 2014, 53, 16143.
/
| 〈 |
|
〉 |
