聚乙二醇功能化离子液体的制备及其在有机反应中的应用

徐艺凇; 张凤香; 厉嘉云; 白赢; 肖文军; 彭家建

doi:10.7536/PC150320

化学进展 ›› 2015, Vol. 27 ›› Issue (10) :1400-1412 DOI: 10.7536/PC150320

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聚乙二醇功能化离子液体的制备及其在有机反应中的应用

徐艺凇, 张凤香, 厉嘉云, 白赢*, 肖文军, 彭家建*

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Preparation and Applications in Organic Reactions of Polyethylene Glycol Functionalized Ionic Liquids

Xu Yisong, Zhang Fengxiang, Li Jiayun, Bai Ying*, Xiao Wenjun, Peng Jiajian*

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文章历史 +

摘要

聚乙二醇功能化离子液体作为一个新的研究方向受到了化学研究者关注,该类离子液体已经成功地应用于许多有机合成反应中,可以明显改善催化剂性能,并可在一定程度上解决传统催化剂使用中遇到的难分离、难回收再利用的问题。本文介绍了聚乙二醇功能化离子液体的发展历程、制备方法和其作为反应介质、溶剂或催化剂在有机合成反应中应用的最新研究成果,主要包括加成反应、缩合反应、还原反应、酯化反应、硝化反应、氧化反应、水解反应、Heck 反应以及Suzuki-Miyaura反应等。

Abstract

The ionic liquids have been widely applied in the organic synthesis as a new reaction medium or catalysts, because of their special properties and excellent solubility with organic and inorganic compounds. Recently, polyethylene glycol-functionalized ionic liquids have attracted much attention from the researchers engaging in organic synthesis. The polyethylene glycol-functionalized ionic liquids merged the physical and chemical properties of ionic liquids and polyethylene glycol, so it can be used as better solvent or reaction medium than that of ionic liquids or polyethylene glycol respectively. On the other hand, the polyethylene glycol-functionalized ionic liquids could be easily modified with different functional groups, which can change the corresponding electronic properties by the modification of their structure. All this will contribute greatly to improve the catalytic performance in polyethylene glycol-functionalized ionic liquids involved organic reactions. The previous progress showed that there are several merits for the application of polyethylene glycol ionic liquids in organic synthesis, not only improved the catalytic activity and selectivity of reaction, but also simplified the work-up, and facilitated the separation and reuse of traditional catalyst. The paper summarizes the synthesis of various polyethylene glycol functionalized ionic liquids, and focused on the recent applications of polyethylene glycol functionalized ionic liquids as new reaction medium, or catalyst in organic reaction, including addition reaction, condensation reaction, reduction reaction, esterification, nitration reaction, oxidation reaction, hydrolysis reaction, Heck reaction, Suzuki-Miyaura coupling reaction, etc.

Contents
1 Introduction
2 Progress and preparation of polyethylene glycol functionalized ionic liquids
3 Application of polyethylene glycol functionalized ionic liquids in the addition reaction
3.1 Hydrosilylation
3.2 Cycloaddition of epoxy compounds with CO₂
4 Application of polyethylene glycol functionalized ionic liquids in the condensation reaction
4.1 Application of polyethylene glycol functionalized ionic liquids/toluene in the acetal reaction
4.2 Condensation reaction of three components
4.3 Condensation reaction of four components
4.4 Knoevenagel condensation reaction
5 Application of polyethylene glycol functionalized ionic liquids in the reduction reaction
5.1 Application of PEG₁₀₀₀-DAIL/toluene in the reduction reaction of aromatic nitro compounds
5.2 Catalytic synthesis of 2-(amino benzene) six fluorine isopropyl alcohol
5.3 Catalytic hydrogenation
6 Application of polyethylene glycol functionalized ionic liquids in the esterification reaction
7 Application of polyethylene glycol functionalized ionic liquids in the nitration
8 Application of polyethylene glycol functionalized ionic liquids in the oxidation reaction
9 Application of polyethylene glycol functionalized ionic liquids in the hydrolysis reaction
10 Application of polyethylene glycol functionalized ionic liquids in the other reaction
11 Conclusion and perspective

Graphical abstract

关键词

聚乙二醇离子液体 / 催化 / 有机合成

Key words

polyethylene glycol functionalized ionic liquid / catalysis / organic synthesis

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徐艺凇, 张凤香, 厉嘉云, 白赢, 肖文军, 彭家建. 聚乙二醇功能化离子液体的制备及其在有机反应中的应用[J]. 化学进展, 2015, 27(10): 1400-1412 DOI:10.7536/PC150320

Xu Yisong, Zhang Fengxiang, Li Jiayun, Bai Ying, Xiao Wenjun, Peng Jiajian. Preparation and Applications in Organic Reactions of Polyethylene Glycol Functionalized Ionic Liquids[J]. Progress in Chemistry, 2015, 27(10): 1400-1412 DOI:10.7536/PC150320

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原文顺序 | 出版日期 | 本文引用

[1] Lee S G. Chem. Commun., 2006, 10: 1049.
[2] Pucheault M, Vaultier M. Top Curr. Chem., 2009, 290: 83.
[3] Giernoth R. Angew Chem. Int. Ed., 2010, 49(16): 2834.
[4] 应安国(Ying A G), 叶伟东(Ye W D), 刘泺(Liu L), 吴国锋(Wu G F), 陈新志(Chen X Z), 钱胜(Qian S), 张秋萍(Zhang Q P). 有机化学(Chinese Journal of Organic Chemistry), 2008, 28(12): 2081.
[5] 钟涛(Zhong T), 乐长高(Le Z G), 谢宗波(Xie Z B), 曹霞(Cao X), 吕雪霞(Lv X X). 有机化学(Chinese Journal of Organic Chemistry), 2010, 30(7): 981.
[6] Chen J, Spear S K, Huddleston J G, Holbrey J D, Swatloski R P, Rogers R D. Green Chem., 2004, 43(17): 5358.
[7] Naik S D, Doraiswamy L K. AIChE J., 1998, 44(3): 612.
[8] Chen J, Spear S K, Huddleston J G, Rogers R D. Green Chem., 2005, 7(2): 64.
[9] Chandrasekhar S, Prakash S J, Rao C L. J. Org. Chem., 2006, 71(5): 2196.
[10] Fraga D J, Famelart M H, Bazureau J P. Org. Proc. Res. Dev., 2002, 6(4): 374.
[11] Jin C M, Ye C F, Phillips B S, Zabinski J S, Liu X Q, Liu W M, Shreeve J M. J. Mater. Chem., 2006, 16(16): 1529.
[12] Zhi H Z, Lv C X, Zhang Q, Luo J. Chem. Commun., 2009, 20: 2878.
[13] Li H, Hou Z S, Qiao Y X, Feng B, Hu Y, Wang X R, Zhao X G. Catal. Commun., 2010, 11(5): 470.
[14] Williams M E, Masui H, Long J W, Malik J, Murray R W. J. Am. Chem. Soc., 1997, 119(8): 1997.
[15] Masui H, Murray R W. Inorg. Chem., 1997, 36(22): 5118.
[16] Long J W, Kim I K, Murray R W. J. Am.Chem. Soc., 1997, 119(47): 11510.
[17] Williams M E, Crooker J C, Pyati R, Lyons L J, Murray R W. J. Am. Chem. Soc., 1997, 119(42): 10249.
[18] Dickinson V E, Williams M E, Hendrichson S M, Masui H, Murray R W. J. Am. Chem. Soc., 1999, 121(4): 613.
[19] Liu N, Liu C, Jin Z.Green Chem., 2012, 14(3): 592.
[20] 付尧(Fu Y). 大连理工大学硕士学位论文(Master Dissertation of Dalian University of Technology), 2014.
[21] 姚美焕(Yao M H), 梁永民(Liang Y M), 夏延秋(Xia Y F), 周峰(Zhou F). 2009年全国摩擦学学术会议(The 2009 National Conference on Tribology),长沙(Changsha). 379.
[22] Wu C, Peng J J, Li J Y, Bai Y, Hu Y Q, Lai G Q. Catal. Commun., 2008, 10(2): 248.
[23] Xu Y S, Bai Y, Peng J J, Li J Y, Xiao W J, Lai G Q. J. Organomet. Chem., 2014, 765: 59.
[24] Calo V, Nacci A, Monopoli A, Fanizzi A. Org. Lett., 2002, 4(15): 2561.
[25] Nishikubo T, Kameyama A, Yamashita J, Tomoi M, Fukuda W. J. Polym. Sci. Part A: Polym. Chem., 1993, 31(4): 939.
[26] Nishikubo T, Kameyama A, Yamashita J, Fukumitsu T, Maejima C, Tomoi M. J. Polym. Sci. Part A: Polym. Chem., 1995, 33(7): 1011.
[27] Ochiai B, Endo T. J. Polym. Sci. Part A: Polym. Chem., 2007, 45(23): 5673.
[28] Takeda N, Inoue S. Bull. Chem. Soc. Jpn., 1978, 51(12): 3564.
[29] Kasuga K, Kato T, Kabata N, Handa M. Bull. Chem. Soc. Jpn., 1996, 69(10): 2885.
[30] Jin L L, Jing H W, Chang T, Bu X L, Wang L, Liu Z L. J. Mol. Catal. A: Chem., 2007, 261(2): 262.
[31] Fujinami T, Suzuki T, Kamiya M, Fukuzawa S, Sakai S. Chem. Lett., 1985, 14(2): 199.
[32] Melendez J, North M, Pasquale R. Eur. J. Inorg. Chem., 2007, 21: 3323.
[33] North M, Pasquale R. Angew. Chem. Int. Ed., 2009, 48(16): 2946.
[34] Berkessel A, Brandenburg M. Org. Lett., 2006, 8(20): 4401.
[35] Yang Z Z, Zhao Y N, He L N, Gao J, Yin Z S. Green Chem., 2012, 14(2): 519.
[36] 姚锐(Yao R). 天津大学硕士论文(Master Dissertation of Tianjin University), 2012.
[37] Smith B M, Graham A E. Tetrahedron Lett., 2006, 47(52): 9317.
[38] Li D M, Shi F, Peng J J, Guo S, Deng Y Q. J. Org. Chem., 2004, 69(10): 3582.
[39] 职慧珍(Zhi H Z), 罗军(Luo J),马伟(Ma W),吕春绪(Lü C X).高等学校化学学报(Chemical Journal of Chinese University), 2008, 29(10): 2007.
[40] Zhi H Z, Lu C X, Zhang Q, Luo J. Chem. Commun, 2009, 2878.
[41] 职慧珍(Zhi H Z). 南京理工大学博士论文(Doctoral Dissertation of Nanjing University of Science and Technology), 2012.
[42] Wang Y L, Li Z, Luo J, Liu Z L. J. Chin. Chem. Soc., 2013, 60(12): 1431.
[43] Kuo S C, Huang L J, Nakamura H. Med. Chem., 1984, 27(4): 539.
[44] 史达清(Shi D Q), 张姝(Zhang S), 庄启亚(Zhuang Q Y), 屠树江(Tu S J), 胡宏纹(Hu H W). 有机化学(Chinese Journal of Organic Chemistry), 2003, 23(11): 1314.
[45] Mecadon H, Rohman M R, Kharbangar I, Laloo B M, Kharkongor I, Rajbangshi M, Myrboh B. Tetrahedron Lett., 2011, 52(25): 3228.
[46] Litvinov Y M, Shestopalov A A, Rodinovskaya L A, Shestopalov A M. J. Comb. Chem., 2009, 11(5): 914.
[47] Ablajan K, Maimaiti Z. Synth. Commun., 2012, 42(13): 1959.
[48] Zou Y, Wu H, Hu Y, Liu H, Zhao X, Ji H L, Shi D Q. Ultrason. Sonochem., 2011, 18(3): 708.
[49] 李晓君(Li X J), 郭红云(Guo H Y). 有机化学(Chinese Journal of Organic Chemistry), 2012, 32(1): 127.
[50] 王英磊(Wang Y L), 罗军(Luo J). 有机化学(Chinese Journal of Organic Chemistry), 2013, 33(9): 2016.
[51] Luo J, Xin T T, Wang Y L. New J. Chem., 2013, 37(2): 269.
[52] 职慧珍(Zhi H Z), 罗军(Luo J), 马伟(Ma W), 吕春绪(Lv C X). 高等学校化学学报(Chemical Journal of Chinese Universities), 2013, 34(3): 573.
[53] 戴燕(Dai Y), 李斌栋(Li B D), 吕春绪(Lv C X). 精细石油化工(Speciality Petrochemicals), 2009, 26(2): 40.
[54] Tan B, Jiang J Y, Wang Y H, Wei L, Chen D J, Jin Z L. Appl. Organomet. Chem., 2008, 22(11): 620.
[55] Zeng Y, Wang Y H, Jiang J Y, Jin Z L. Catal. Commun., 2012, 19: 70.
[56] Wei L, Jiang J Y, Wang Y H, Jin Z L. J. Mol. Catal. A: Chem., 2004, 221(1/2): 47.
[57] 郑明东(Zheng M D), 陈同云(Chen T Y ), 胡克良(Hu K L).高等学校化学学报(Chemical Journal of Chinese Universities), 2006, 27(6): 1086.
[58] 王会萍(Wang H P), 商艳梅(Shang Y M), 王磊(Wang L), 李叶芝(Li Y Z), 黄化民(Huang H M). 高等学校化学学报(Chemical Journal of Chinese Universities), 2006, 27(5): 894.
[59] 职慧珍(Zhi H Z), 罗军(Luo J), 马伟(Ma W), 吕春绪(Lv C X). 高等学校化学学报(Chemical Journal of Chinese Universities), 2008, 29(4): 772.
[60] Wu Q, Wan H, Li H, Song H, Chu T. Catal. Today, 2013, 200(1): 74.
[61] Laali K K, Gettwert V J. J. Org. Chem., 2001, 66(1): 35.
[62] Smith K, Liu S, El-Hiti G A. Ind. Eng. Chem. Res., 2005, 44(23): 8611.
[63] Fang D, Shi Q R, Cheng J, Gong K, Liu Z L. Appl. Catal. A, 2008, 345(2): 158.
[64] Wang P C, Lu M. Tetrahedron Lett., 2011, 52(13): 1452.
[65] Mallat T, Baiker A. Chem. Rev., 2004, 104(6): 3037.
[66] Ghorbani-Choghamarani A, Azadi G. J. Iran. Chem. Soc., 2011, 8(4): 1082.
[67] Hajipour A R, Khazdooz L, Ruoho A E. J. Iran. Chem. Soc., 2011, 8(2): 382.
[68] Hu Y L, Lu M, Ge X T. J. Iran. Chem. Soc., 2013, 10(3): 453.
[69] Lu T T, Mao Y, Yao K, Xu J, Lu M. Catal. Commun., 2012, 27: 124.
[70] Beste G W, Hammett L P. J. Am. Chem. Soc., 1940, 62: 2481.
[71] Saramma K, Anantarman R. Proc. Indian Acad. Sci. Sect. A, 1959, 49(2): 111.
[72] Shi M, Feng Y S. J. Org. Chem., 2001, 66(9): 3235.
[73] Leonid G M, Andrei V V, Olga S K, Oleg M N. Mendeleev Commun., 1995, 5(6): 223.
[74] Xing M K, Si Q C, Juan D, Xiao Q Y, Xian C Z. J. Mol. Catal. A: Chem., 2004, 210(1/2): 23.
[75] Bazzicalupi C, Bencini A, Berni E, Di Vaira M. Inorg. Chim. Acta, 2005, 358: 77.
[76] Mohile S S, Potdar M K, Harjani J R, Nara S J, Salunkhe M M, Swapnil S M, Mahesh K P. J. Mol. Catal. B: Enzylmatic., 2004, 30(5/6): 185.
[77] 蒋辉(Jiang H), 陆明(Lu M). 南京理工大学硕士论文, (Master Dissertation of Nanjing University of Science and Technology), 2011.
[78] Hu Y L, Jiang H, Zhu J, Lu M. New J. Chem., 2011, 35(2): 292.
[79] Wang L, Zhang Y H, Xie C S, Wang Y G. Synlett, 2005, 12: 1861.
[80] Li B, Li Y Q, Zheng J. ARKIVOC, 2010, 9: 163.
[81] Wang J Y, Xu B L, Sun H Y, Song G H. Tetrahedron Lett., 2013, 54(3): 238.
[82] Wang Y L, Luo J, Liu Z L. Appl. Organomet. Chem., 2013, 27(10): 601.
[83] Hu Y L, Lu M, Ge Q, Wang P C, Lu T T. J. Ind. Eng. Chem., 2010, 16 (4): 615.
[84] 陆鸿飞(Lu H F), 孙垒垒(Sun L L), 武鼎铭(Wu D M),高玉华(Gao Y H), 石亚丽(Shi Y L), 薛芹(Xue Q). 有机化学(Chinese Journal of Organic Chemistry), 2012, 32(10): 1880.