Chinese Journal of Organic Chemistry >
Asymmetric Addition Reaction Catalyzed by 1- (2-Hydroxynaphtha-len-1-yl)naphthalen-2-ol Functionalized Porous Organic Polymer
Received date: 2018-04-08
Revised date: 2018-05-25
Online published: 2018-06-07
Supported by
Project supported by the National Natural Science Foundation of China (No. 21271129).
A functionalized porous organic polymer POP-BINOL has been prepared and characterized by various techniques including carbon-13 cross-polarization magic-angle spinning nuclear magnetic resonance (13C CP/MAS NMR), fourier transform infrared spectroscopy (FT-IR), powder X-ray diffraction (pXRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), nitrogen adsorption and thermogravimetric analysis (TG). After being treated with Ti (OiPr)4, the composite material could be used as highly effective and reusable heterogeneous catalyst for asymmetric diethylzinc addition to aldehydes with medium and upper ee value.
Kong Shengnan , Qian Xuefeng , Shu Mouhai , Xiao Wende . Asymmetric Addition Reaction Catalyzed by 1- (2-Hydroxynaphtha-len-1-yl)naphthalen-2-ol Functionalized Porous Organic Polymer[J]. Chinese Journal of Organic Chemistry, 2018 , 38(10) : 2754 -2760 . DOI: 10.6023/cjoc201804011
[1] (a) Wang, C. A.; Wang, W. Acta Chim. Sinica 2015, 73, 498(in Chinese). (王昌安, 王为, 化学学报, 2015, 73, 498.)
(b) Ren, H.; Zhu, G. S. Acta Chim. Sinica 2015, 73, 587(in Chinese). (任浩, 朱广山, 化学学报, 2015, 73, 587.)
[2] (a) Zhao, W.; Xia, L.; Liu, X. CrystEngComm 2018, 20, 1613.
(b) Liu, G.; Sheng, J.; Zhao, Y. Sci. China, Chem. 2017, 60, 1015.
[3] (a) Jiang, J. X.; Su, F.; Trewin, A.; Wood, C. D.; Campbell, N. L. Niu, H. J.; Dickinson, C.; Ganin, A. Y.; Rosseinsky, M. J.; Khimyak, Y. Z.; Cooper, A. I. Angew. Chem., Int. Ed. 2007, 119, 8574.
(b) Xu, Y.; Zhang, C.; Mu, P.; Mao, N.; Wang, X.; He, Q.; Wang, F.; Jiang, J. X. Sci. China, Chem. 2017, 60, 1075.
[4] (a) Zhou, Y. B.; Zhan, Z. P. Chem.-Asian J. 2018, 13, 9.
(b) Wu, K. Y.; Guo, J. Acta Chim. Sinica 2015, 73, 480(in Chinese). (吴可义, 郭佳, 化学学报, 2015, 73, 480.)
[5] Lee, J. S. M.; Briggs, M. E.; Hu, C. C.; Cooper, A. Nano Energy 2018, 46, 277.
[6] (a) Sato, H.; Nakajo, S.; Oishi, Y.; Shibasaki, Y. React. Funct. Polym. 2018, 125, 70.
(b) McKeown, N. B. Sci. China, Chem. 2017, 60, 1023.
[7] Schmidt, J.; Werner, M.; Thomas, A. Macromolecules 2009, 42, 4426.
[8] Zhang, P.; Weng, Z.; Guo, J.; Wang, C. C. Chem. Mater. 2011, 23, 5243.
[9] Sun, L. B.; Liang, Z. Q.; Yu, J. H.; Xu, R. R. Polym. Chem. 2013, 4, 1932.
[10] (a) Pandey, P.; Farha, O. K.; Spokoyny, A. M.; Mirkin, C. A.; Kanatzidis, M. G.; Hupp, J. T.; Nguyen, S. T. J. Mater. Chem. 2011, 21, 1700.
(b) Li, L.; Zhao, H.; Wang, J.; Wang, R. ACS Nano 2014, 8, 5352.
(c) Plietzsch, O.; Schilling, C. I.; Grab, T.; Grage, S. L.; Ulrich, A. S.; Comotti, A.; Sozzani, P.; Muller, T.; Brase, S. New J. Chem. 2011, 35, 1577.
(d) Kong, S. N.; Malik, A. U.; Qian, X. F.; Shu, M. H.; Xiao, W. D. Chin. J. Org. Chem. 2018, 38, 656(in Chinese). (孔胜男, Abaid Ullah Malik, 钱雪峰, 舒谋海, 肖文德, 有机化学, 2018, 38, 656.)
[11] Modak, A.; Mondal, J.; Bhaumik, A. ChemCatChem 2013, 5, 1749.
[12] Gomes, R.; Bhanja, P.; Bhaumik, A. J. Mol. Catal. A:Chem. 2016, 411, 110.
[13] Côté, A. P.; Benin, A. I.; Ockwig, N. W.; O'Keeffe, M.; Matzger, A. J.; Yaghi, O. M. Science 2005, 310, 1166.
[14] Spitler, E. L.; Dichtel, W. R. Nat. Chem. 2010, 2, 672.
[15] Kuhn, P.; Antonietti, M.; Thomas, A. Angew. Chem., Int. Ed. 2008, 47, 3450.
[16] Wang, K. W.; Yang, L. M.; Wang, X.; Guo, L. P.; Cheng, G.; Zhang, C.; Jin, S. B.; Tan, B.; Cooper, A. Angew. Chem., Int. Ed. 2017, 56, 14149.
[17] (a) Zhang, W.; Aguila, B.; Ma, S. J. Mater. Chem. A 2017, 5, 8795.
(b) Wang, M.; Guo, L.; Cao, D. Sci. China, Chem. 2017, 60, 1090.
(c) Li, Y. Q.; Ben, T.; Qiu, S. L. Acta Chim. Sinica 2015, 73, 605(in Chinese). (李艳强, 贲腾, 裘式纶, 化学学报, 2015, 73, 605.)
(d) Huang, N.; Day, G.; Yang, X.; Drake, H.; Zhou, H. C. Sci. China. Chem. 2017, 60, 1007.
(e) Lu, S.; Jin, Y.; Gu, H.; Zhang, W. Sci. China, Chem. 2017, 60, 999.
(f) Wan, G.; Fu, Y.; Guo, J.; Xiang, Z. Acta Chim. Sinica 2015, 73, 557(in Chinese). (万刚, 付玉昂, 郭佳宁, 向中华, 化学学报, 2015, 73, 557.)
(g) Zhou, B. L.; Chen, L. Acta Chim. Sinica 2015, 73, 487(in Chinese). (周宝龙, 陈龙, 化学学报, 2015, 73, 487.)
[18] Wang, T.; Zhao, Y. C.; Luo, M.; Zhang, L. M.; Cui, Y.; Zhang, C. S.; Han, B. H. Polymer 2015, 60, 26.
[19] Sang, N.; Zhan, C.; Cao, D. J. Mater. Chem. A 2015, 3, 92.
[20] Li, R.; Wang, Z. J. Wang, L.; Ma, B. C.; Ghasimi, S.; Lu, H.; Landfester, K.; Zhang, K. A. I. ACS Catal. 2016, 6, 1113.
[21] Li, X. C.; Zhang, Y.; Wang, C. Y.; Wan, Y.; Lai, W. Y.; Pang, H.; Huang, W. Chem. Sci. 2017, 8, 2959.
[22] (a) Ma, L.; Wanderley, M. M.; Lin, W. ACS Catal. 2011, 1, 691.
(b) Noyori, R.; Tomino, I.; Tanimoto, Y. J. Am. Chem. Soc. 1979, 101, 3129.
(c) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988,110, 310.
(d) Mikami, K.; Matsukawa, S.; Volk, T.; Terada, M. Angew. Chem., Int. Ed. 1997, 36, 2768.
(e) Ma, M. F. P.; Li, K.; Zhou, Z.; Tang, C.; Chan, A. S. C. Tetrahedron:Asymmetry 1999, 10, 3259.
(f) Wang, X.; Wang, X.; Guo, H.; Wang, Z.; Ding, K. Chem.-Eur. J. 2005, 11, 4078.
(g) Wang, X.; Shi, L.; Li, M.; Ding, K. L. Angew. Chem., Int. Ed. 2005, 44, 6362.
[23] Liu, D.; Ouyang, K.; Yang, N. Tetrahedron 2016, 47, 1018.
[24] Zhao, Y.; Li, J.; Li, C.; Yin, K.; Ye, D.; Jia, X. Green Chem. 2010, 12, 1370.
[25] Valente, C.; Choi, E.; Belowich, M. E.; Doonan, C. J.; Li, Q.; Gasa, T. B.; Botros, Y. Y.; Yaghi, O. M.; Stoddart, J. F. Chem. Commun. 2010, 46, 4911.
[26] (a) Zhang, Y.; Zhang, Y.; Sun, Y. L.; Du, X.; Shi, J. Y.; Wang, W. D.; Wang, W. Chem.-Eur. J. 2012, 18, 6328.
(b) Kiskan, B.; Antonietti, M.; Weber, J. Macromolecules 2012, 45, 1356.
[27] Wang, X.; Han, X.; Zhang, J.; Wu, X.; Liu, Y.; Cui, Y. J. Am. Chem. Soc. 2017, 138, 12332.
[28] Aga, M. A.; Kumar, B.; Rouf, A.; Shah, B. A.; Taneja, S. C. Tetrahedron Lett. 2014, 55, 2639.
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