Polyethylene Glycol: A New Medium for Green Organic Synthesis
- Corresponding author: Xiao Liwei, xiaoliwei2000@sina.com
Citation:
Xiao Liwei, Dai Fucai, Li Zheng, Jing Xuemin, Kong Jie, Liu Guangxian. Polyethylene Glycol: A New Medium for Green Organic Synthesis[J]. Chinese Journal of Organic Chemistry,
;2019, 39(3): 648-660.
doi:
10.6023/cjoc201807056
Zhang, M.; Liu, Y.-H.; Shang, Z.-R.; Hu, H.-C.; Zhang, Z.-H. Catal. Commun. 2017, 88, 39.
doi: 10.1016/j.catcom.2016.09.028
Zhang, M.; Fu, Q.-Y.; Gao, G.; He, H.-Y.; Zhang, Y.; Wu, Y.-S.; Zhang, Z.-H. ACS Sustainable Chem. Eng. 2017, 5, 6175.
doi: 10.1021/acssuschemeng.7b01102
Gu, Y. Green Chem. 2012, 14, 2091.
doi: 10.1039/c2gc35635j
Liu, P.; Hao, J.-W.; Mo, L.-P.; Zhang. Z.-H. RSC Adv. 2015, 5, 48675.
doi: 10.1039/C5RA05746A
Gao, G.; Wang, P.; Liu, P.; Zhang, W.; Mo, L.; Zhang, Z. Chin. J. Org. Chem. 2018, 38, 846(in Chinese).
Chen, J.; Spear, S. K.; Huddleston, J. G.; Rogers, R. D. Green Chem. 2005, 7, 64.
doi: 10.1039/b413546f
Zhou, H.; Fan, Q.; He, Y.; Gu, L.; Chan, A. S. C. Prog. Chem. 2007, 19, 1517(in Chinese).
doi: 10.6023/cjoc201711014
Yin, L.; Zhang, Z.-H.; Wang, Y.-M. Tetrahedron 2006, 62, 9359.
doi: 10.1016/j.tet.2006.07.067
Li, J.; Liu, W.; Xie, Y. J. Org. Chem. 2005, 70, 5409.
doi: 10.1021/jo050353m
Li, J.; Hu, X.; Liang, Y.; Xie, Y. Tetrahedron 2006, 62, 3.
doi: 10.1016/S0040-4020(06)00445-5
Liu, L.; Zhang, Y.; Wang, Y. J. Org. Chem. 2005, 70, 6122.
doi: 10.1021/jo050724z
Silva, A.; Senra, J.; Aguiar, L. Tetrahedron Lett. 2010, 51, 3883.
doi: 10.1016/j.tetlet.2010.04.092
Han, W.; Liu, C.; Jin, Z. Org. Lett. 2007, 9, 4005.
doi: 10.1021/ol701709q
Razler, T. M.; Hsiao, Y.; Qian, F.; Fu, R.; Khan, R. K.; Doubleday, W. J. Org. Chem. 2009, 74, 1381.
doi: 10.1021/jo802277z
Mao, J.; Guo, J.; Fang, F.; Ji, S.-J. Tetrahedron 2008, 64, 3905.
doi: 10.1016/j.tet.2008.02.068
Chandrasekhar, S.; Narsihmulu, C.; Sultana, S. S.; Reddy, N. R. Org. Lett. 2002, 4, 4399.
doi: 10.1021/ol0266976
Nowrouzi, N.; Zarei, M. Tetrahedron 2015, 71, 7847.
doi: 10.1016/j.tet.2015.08.023
Declerck, V.; Lamaty, F. Eur. J. Org. Chem. 2007, 1, 201.
Luo, C.; Zhang, Y.; Wang, Y. J. Mol. Catal. A:Chem. 2005, 229, 7
doi: 10.1016/j.molcata.2004.10.039
Datta, G. K.; Schenck, H.; Hallberg, A.; Larhed, M. J. Org. Chem. 2006, 71, 3896.
doi: 10.1021/jo0602367
Zhou, W; Wang, K.; Wang, J. J. Org. Chem. 2009, 74, 5599.
doi: 10.1021/jo9005206
Xin, B.; Zhang, Y.; Cheng, K. J. Org. Chem. 2006, 71, 5725.
doi: 10.1021/jo060749d
Close, A. J.; Kemmitt, P.; Emmerson, M. K.; Spence, J. Tetrahedron 2014, 70, 9125.
doi: 10.1016/j.tet.2014.09.044
Ackermann, L.; Vicénte, R. Org. Lett. 2009, 11, 4922.
doi: 10.1021/ol9020354
Kabalka, G. W.; Dong, G.; Venkataiah, B.; Chen, C. J. Org. Chem. 2005, 70, 9207.
doi: 10.1021/jo051177k
Li, J.-H.; Zhu, Q.-M.; Liang, Y.; Yang, D. J. Org. Chem. 2005, 70, 5347.
doi: 10.1021/jo0506635
Shi, S.; Zhang, Y. J. Org. Chem. 2007, 72, 5927.
doi: 10.1021/jo070855v
Srimani, D.; Sawoo, S.; Sarkar, A. Org. Lett. 2007, 9, 3639.
doi: 10.1021/ol7015143
Bortolini, O.; Fantin, G.; Fogagnolo, M.; Giovannini, P. P.; Venturi, V.; Pacifico, S.; Massi, A. Tetrahedron 2011, 67, 8110.
doi: 10.1016/j.tet.2011.08.056
Mao, J.; Hua, Q.; Xie, G.; Yao, Z.; Shi, D. Eur. J. Org. Chem. 2009, 2262.
Wang, L.; Zhang, Y.; Liu, L.; Wang, Y. J. Org. Chem. 2006, 71, 1284.
doi: 10.1021/jo052300a
Li, X.; Yuan, T.; Yang, Y.; Chen, J. Tetrahedron 2004, 70, 9652
Chen, J.; Zhang, Y.; Hao, W.; Zhang, R.; Yi, F. Tetrahedron 2013, 69, 613.
doi: 10.1016/j.tet.2012.11.014
Colacino, E.; Villebrun, L.; Martinez, J.; Lamaty, F. Tetrahedron 2010, 66, 3730.
doi: 10.1016/j.tet.2010.03.065
Burley, G. A.; Davies, D. L.; Griffith, G. A.; Lee, M.; Singh, K. J. Org. Chem. 2010, 75, 980.
doi: 10.1021/jo902466f
Spina, R.; Colacino, E.; Gabriele, B.; Salerno, G.; Martinez, J.; Lamaty, F. J. Org. Chem. 2013, 78, 2698.
doi: 10.1021/jo302474r
Lara, R. G.; Rosa, P. C.; Soares, L. K.; Silva, M. S.; Jacob, R. G.; Perin, G. Tetrahedron 2012, 68, 10414.
doi: 10.1016/j.tet.2012.08.055
Chatterjee, T.; Ranu, B. C. J. Org. Chem. 2013, 78, 7145.
doi: 10.1021/jo401062k
Firouzabadi, H.; Iranpoor, N.; Abbasi, M. Tetrahedron 2009, 65, 5293.
doi: 10.1016/j.tet.2009.04.079
She, J.; Jiang, Z.; Wang, Y. G. Tetrahedron Lett. 2009, 50, 593.
doi: 10.1016/j.tetlet.2008.11.082
Lu, J.; Guan, Z.-Z.; Gao, J.-W.; Zhang, Z.-H. Appl. Organomet. Chem. 2011, 25, 537.
doi: 10.1002/aoc.v25.7
Wang, P.; Lu, J.; Zhang, Z.-H. J. Chem. Res. 2013, 359
doi: 10.3184/174751913X13686082295417
Xiao, L.; Gao, H.; Ren, L.; Kang, J. Chin. J. Appl. Chem. 2015, 32, 304(in Chinese).
doi: 10.11944/j.issn.1000-0518.2015.03.140228
Yang, X.; Li, C.; Ma, J.; Wang, C.; Zhang, L. Chem. Res. Appl. 2010, 22, 1004(in Chinese).
doi: 10.3969/j.issn.1004-1656.2010.08.008
Modugu, N. R.; Pittala, P. K. New J. Chem. 2017, 41, 14062.
doi: 10.1039/C7NJ03515B
Zhang, X.-N.; Li, Y.-X.; Zhang, Z-H. Tetrahedron 2011, 67, 7426.
doi: 10.1016/j.tet.2011.07.002
Zareai, Z.; Khoobi, M.; Ramazani, A.; Foroumadi, A.; Souldozi, A.; Slepokura, K.; Lis, T.; Shafiee, A. Tetrahedron 2012, 68, 6721.
doi: 10.1016/j.tet.2012.05.112
Balwe, S. G.; Lim, K. T.; Cho, B. G.; Jeong, Y. T. Tetrahedron 2017, 73, 3564.
doi: 10.1016/j.tet.2017.05.047
Jain, S. L.; Singhal, S.; Sain, B. Green Chem. 2007, 9, 740.
doi: 10.1039/b702311a
Kidwai, M.; Bhatnagar, D. Tetrahedron Lett. 2010, 51, 2700.
doi: 10.1016/j.tetlet.2010.03.033
Kidwai, M.; Bhatnagar, D.; Mishra, N. K. Catal. Commun. 2008, 9, 2547.
doi: 10.1016/j.catcom.2008.07.010
Hasaninejad, A.; Beyrati, M. RSC Adv. 2018, 8, 1934.
doi: 10.1039/C7RA13133J
Survase, D.; Bandgar, B.; Helavi, V. Synth. Commun. 2017, 47, 680.
doi: 10.1080/00397911.2017.1278774
Reddy, M. V.; Kim, J. S.; Lim, K. T.; Jeong, Y. T Tetrahedron Lett. 2014, 55, 6459.
doi: 10.1016/j.tetlet.2014.09.135
Chandrasekhar, S.; Prakash, S. J.; Rao, C. L. J. Org. Chem. 2006, 71, 2196.
doi: 10.1021/jo052604x
Xu, C.; Huang, B.; Yan, T.; Cai, M. Green Chem. 2018, 20, 391.
doi: 10.1039/C7GC02823G
Wang, X.; Quan, Z.; Zhang, Z. Tetrahedron 2007, 63, 8227.
doi: 10.1016/j.tet.2007.05.108
Kumar, D.; Patel, G.; Mishra, B. G.; Varma, R. S. Tetrahedron Lett. 2008, 49, 6974.
doi: 10.1016/j.tetlet.2008.09.116
Billault, I.; Pessel, F.; Petit, A.; Turgis, R.; Scherrmann, M.-C. New J. Chem. 2015, 39, 1986.
doi: 10.1039/C4NJ01784F
Kumaraswamy, G.; Ankamma, K.; Pitchaiah, A. J. Org. Chem. 2007, 72, 9822.
doi: 10.1021/jo701724f
Chandrasekhar, S.; Reddy, N. R.; Sultana, S. S.; Narsihmulu, C.; Reddy, K. V. Tetrahedron 2006, 62, 338.
doi: 10.1016/j.tet.2005.09.122
Dawane, B. S.; Konda, S. G.; Shaikh, B. M.; Bhosale, R. B. Acta Pharm. 2009, 59, 473.
doi: 10.2478/v10007-009-0034-7
Liu, Y.; Liang, J.; Liu, X. H.; Fan, J. C.; Shang, Z. C. Chin. Chem. Lett. 2008, 19, 1043.
doi: 10.1016/j.cclet.2008.06.016
Wang, X.; Ye, H.; Quan, Z. J. Northwest Normal Univ. (Nat. Sci.) 2009, 45, 79(in Chinese).
doi: 10.3969/j.issn.1001-988X.2009.03.021
Ballini, R.; Barboni, L.; Alessandro, P. Green Chem. 2008, 10, 1004.
doi: 10.1039/b805985c
Yadav, G. D.; Motirale, B. G. Org. Process Res. Dev. 2009, 13, 341.
doi: 10.1021/op800206c
Guravaiah, N.; Rao, V. R. J. Chem. Res. 2009, 237.
doi: 10.3184/030823410X12652994990526
Jawale, D. V.; Lingampalle, D. L.; Pratap, U. R.; Mane, R. A. Chin. Chem. Lett. 2010, 21, 412.
doi: 10.1016/j.cclet.2009.11.035
Zhu, D.; Chen, J.; Xiao, H.; Liu, M.; Ding, J.; Wu, H. Synth. Commun. 2009, 39, 2895,
doi: 10.1080/00397910802691874
Lin, P.; Hou, R.; Wang, H.; Kang, I.; Chen, L. J. Chin. Chem. Soc. 2009, 56, 455.
doi: 10.1002/jccs.v56.3
Mukhopadhyay, C.; Tapaswi, P. K. Tetrahedron Lett. 2008, 49, 6237.
doi: 10.1016/j.tetlet.2008.08.041
Deligeorgiev, T. G.; Kaloyanova, S.; Vasilev, A.; Vaquero, J. J. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 2292.
doi: 10.1080/10426501003598648
Liu, L.; Zhang, F.; Wang, H.; Zhu, N.; Liu, B.; Hong, H.; Han, L. Phosphorus, Sulfur Silicon Relat. Elem. 2017, 192, 464.
doi: 10.1080/10426507.2016.1259227
Wang, X.; Gong, H.; Quan, Z.; Li, L.; Ye, H. Chin. Chem. Let. 2009, 20, 44.
doi: 10.1016/j.cclet.2008.10.005
Wang, J.; Song, X. J. Northwest Normal Univ. (Nat. Sci.) 2010, 46, 78(in Chinese).
doi: 10.3969/j.issn.1001-988X.2010.02.018
Nalage, S. V.; Kalyankar, M. B.; Patil, V. S.; Bhosale, S. V.; Deshmukh, S. U.; Pawar, R. P. Open Catal. J. 2010, 3, 58.
doi: 10.2174/1876214X01003010058
Xiao, L.; Gao, H.; Kong, J.; Liu, G.; Li, L.; Duan, J. Chin. J. Org. Chem. 2014, 34, 2511(in Chinese).
Rao, H. S. P.; Jothilingama, S.; Scheerenb, H. W. Tetrahedron 2004, 60, 1625.
doi: 10.1016/j.tet.2003.11.087
Zhao, H.; Zhang, T.; Yan, T.; Cai, M. J. Org. Chem. 2015, 80, 8849.
doi: 10.1021/acs.joc.5b01388
Mukhopadhyay, C.; Tapaswi, P. K.; Butcher, R. J. Org. Biomol. Chem. 2010, 8, 4720.
doi: 10.1039/c0ob00177e
Nakka, M.; Tadikonda, R.; Rayavarapu, S.; Sarakula, P.; Vidavalur, S. Synthesis 2015, 47, 517.
doi: 10.1055/s-0034-1378909
Cho, C. S.; Ren, W. X.; Yoon, N. S. J. Mol. Catal. A:Chem. 2009, 299, 117.
doi: 10.1016/j.molcata.2008.10.024
Zhang, X. Z.; Wang, J. X.; Sun, Y. J.; Zhan, H. W. Chin. Chem. Lett. 2010, 21, 395.
doi: 10.1016/j.cclet.2009.12.015
He, Q.; Wang, J.; Feng, R. Lett. Org. Chem. 2010, 7, 172.
doi: 10.2174/157017810790796228
Jorapur, Y.; Rajagopal, G.; Saikia, P.; Pal, R. R. Tetrahedron Lett. 2008, 49, 1495.
doi: 10.1016/j.tetlet.2007.12.115
Liang, J.; Lv, J.; Shang, Z. C. Tetrahedron 2011, 67, 8532.
doi: 10.1016/j.tet.2011.08.091
Liao, Y.; Wei, T.; Yan, T.; Cai, M. Tetrahedron 2017, 73, 1238.
doi: 10.1016/j.tet.2017.01.023
Wang, J.-Q.; Cai, F.; Wang, E.; He, L.-N. Green Chem. 2007, 9, 882.
doi: 10.1039/b701875d
Chandrasekhar, S.; Reddy, N. K.; Kumar, V. P. Tetrahedron Lett. 2010, 51, 3623.
doi: 10.1016/j.tetlet.2010.05.006
Guo, W.; Liu, Y.; Li, C. Org. Lett. 2017, 19, 1044
doi: 10.1021/acs.orglett.7b00032
Martirosyan, A.; Tamazyan, R.; Gasparyan, S.; Alexanyan, M.; Panosyan, H.; Martirosyan, V.; Schinazi, R. Tetrahedron Lett. 2010, 51, 231.
doi: 10.1016/j.tetlet.2009.11.010
Zhou, H. F.; Fan, Q. H.; Huang, Y. Y.; Wu, L.; He, Y. M.; Tang, W. J.; Gu, L. Q.; Chan, A. S. C. J. Mol. Catal. A:Chem. 2007, 275, 47.
doi: 10.1016/j.molcata.2007.05.029
Liu, W.; Wang, F. Tetrahedron Lett. 2017, 58, 1673.
doi: 10.1016/j.tetlet.2017.03.016
Ding, M.; Jiang, X.; Peng, J.; Zhang, L.; Cheng, Z.; Zhu, X. Green Chem. 2015, 17, 271.
doi: 10.1039/C4GC01169D
Huang, X.; Liu, J.; Sheng, J.; Song, X.; Du, Z.; Li, M.; Zhang, X.; Zou, Y. Green Chem. 2018, 20, 804.
doi: 10.1039/C7GC02994B
Zhang, Z.-H. Monatsh. Chem. 2005, 136, 1191.
doi: 10.1007/s00706-005-0298-7
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