Chinese Journal of Organic Chemistry >
Chitosan@Cu2O as A Facile, Efficient and Reusable Catalyst for Ligand-Free C-O and C-N Coupling
Received date: 2018-12-02
Revised date: 2019-04-04
Online published: 2019-04-16
Supported by
Project supported by the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (No. 14JKD150009) and the Key Projects of Innovation and Entrepreneurship Training Program for College Students in Jiangsu Province (No. 201710324003Z).
The coupling reactions of phenols and nitrogen hetereocycles with aryl halide were catalyzed by a highly active, readily available and easily recoverable heterogeneous Cu catalyst which was prepared by simply stirring an suspension of chitosan in solvent with copper compound. The result showed that chitosan@Cu2O catalyst catalyzed the coupling reactions of aryl halides with phenols and nitrogen hetereocycles to readily give the corresponding products in moderate to excellent yields. The highly active catalyst can be reused many times without losing its catalytic activity.
Key words： chitosan@Cu catalyst; synthesize; catalyze; Cross-coupling
Qian Cunwei , Zhu Wenqian , Liu Junlong , Wang Xuemin , Qiu Ligan . Chitosan@Cu2O as A Facile, Efficient and Reusable Catalyst for Ligand-Free C-O and C-N Coupling[J]. Chinese Journal of Organic Chemistry, 2019 , 39(6) : 1695 -1703 . DOI: 10.6023/cjoc201812003
[1] For reviews, see:
(a) Lindley, J. Tetrahedron 1984, 40, 1433.
(b) Theil, F. Angew. Chem. Int. Ed. 1999, 38, 2345.
(c) Sawyer, J. S. Tetrahedron 2000, 56, 5045.
(d) Thomas, A. W.; Ley, S. V. Angew. Chem. Int. Ed. 2003, 42, 5400.
(e) Kunz, K.; Scholz, U.; Ganzer, D. Synlett. 2003, 15, 2428.
(f) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
[2] For selected examples of medicinally important diaryl ethers, see:
(a) Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909.
(b) Singh, S. B.; Pettit, G. R. J. Org. Chem. 1990, 55, 2797.
(c) Deshpande, V. E.; Gohkhale, N. J. Tetrahedron Lett. 1992, 33, 4213.
(d) Evans, D. A.; DeViries, K. M. In Glycopeptide Antibiotics, Drugs and the Pharmaceutical Sciences, Ed.:Nagarajan, R., Marcel Decker, New York, 1994, p. 63.
(e) Zenitani, S.; Tashiro, S.; Shindo, K.; Nagai, K.; Suzuki, K.; Imoto, M.; Gerfelin, A. J. Antibiot 2003, 56, 617.
(f) Cristau, P.; Vors, J. P.; Zhu, J. Tetrahedron 2003, 59, 7859.
(g) Qian, C. W.; Pang, Y.; Fang, D.; Zong, Q. Chin. J. Pestic. Sci. 2013, 15, 44 (in Chinese).
[3] (a) Ullmann, F. Dtsch, Ber. Chem. Ges 1904, 37, 853.
(b) Ullmann, F. Dtsch, Ber. Chem. Ges. 1903, 36, 2382.
[4] (a) Mann, G.; Hartwig, J. F. Tetrahedron Lett. 1997, 46, 8005.
(b) Palucki, M.; Wolfe, J. P.; Bukhwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333.
(c) Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 13109.
(d) Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369.
(e) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413.
(f) Palucki, M. J.; Wolfe, P.; Buchwald, S. J. Am. Chem. Soc. 119, 3395.
(g) Widenhoefer, R. A.; Zhong, H. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6787.
[5] Marcoux, J. F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539.
[6] Ma, D.; Cai, Q. Org. Lett. 2003, 5, 3799.
[7] Chen, Y. J.; Chen, H. H. Org. Lett. 2006, 8, 5609.
[8] Rao, H.; Jin, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Chem.-Eur. J. 2006, 12, 3636.
[9] Wolter, M.; Nordmann, G.; Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 973.
[10] Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315.
[11] Qian, C.; Zong, Q.; Fang, D. Chin. J. Chem. 2012, 30, 199.
[12] Qian, C.; Xu, S.; Fang, D.; Zong, Q. Chin. J. Chem. 2012, 30, 1881.
[13] Buck, E.; Song, Z.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623.
[14] Lv, X.; Bao, W. J. Org. Chem. 2007, 72, 3863.
[15] Qian, C.; Qin, L.; Zong, Q.; Wu, L.; Fang, D. Bull. Korean Chem. Soc. 2013, 34, 3915.
[16] Qian, C.; Lv, W.; Zong, Q.; Wang, M.; Fang, D. Chin. Chem. Lett. 2014, 25, 337.
[17] Gawande, M. B.; Goswami, A.; Felpin, F.; Asefa, T.; Huang, X.; Silva, R.; Zou, X.; Zboril, R. R.; Varma, S. Chem. Rev. 2016, 116, 3722.
[18] Zhao, H.; Xu, J.; Wang, T. Appl. Catal. A:Gen. 2015, 502, 188.
[19] Honraedt, A.; Le Callonnec, F.; Le Grognec, E.; Fernandez, V.; Felpin, F.-X. J. Org. Chem. 2013, 78, 4604.
[20] Mondal, P.; Sinha, A.; Salam, N.; Roy, A. S.; Jana, N. R.; Islam, S. M. RSC Adv. 2013, 3, 5615.
[21] Hajipour, A. R.; Dordahan, F.; Rafiee, F.; Mahdavi, M. Appl. Organomet. Chem. 2014, 28, 809.
[22] Nador, F.; Volpe, M. A.; Alonso, F.; Radivoy, G. Tetrahedron 2014, 70, 6082.
[23] Baig, R. B. N.; Varma, R. S. Chem. Commun. 2012, 48, 2582.
[24] Sharma, R. K.; Gaur, R.; Yadav, M.; Rathi, A. K.; Pechousek, J.; Petr, M.; Zboril, R.; Gawande, M. B. ChemCatChem 2015, 7, 3495.
[25] Gopiraman, M.; Ganesh Babu, S.; Khatri, Z.; Kai, W.; Kim, Y. A.; Endo, M.; Karvembu, R.; Kim, I. S. Carbon 2013, 62, 135.
[26] (a) Carlo, G. Di; Curulli, A.; R. Toro, G.; Bianchini, C.; De Caro, T.; Padeletti, G.; Zane, D.; Ingo, G. M. Langmuir 2012, 28, 5471.
(b) Yang, Y.-H.; Cui, J.-H.; Zheng, M.-T.; Hu, C.-F.; Tan, S.-Z.; Xiao, Y.; Yang, Q.; Liu, Y.-L. Chem. Commun. 2012, 48, 380.
[27] Hardy, J. J. E.; Hubert, S.; Macquarrie, D. J.; Wilson, A. J. Green Chem. 2004, 6, 53.
[28] Kadib, A. E.; Molvinger, K.; Bousmina M.; Brunel, D. Org. Lett. 2010, 12, 948.
[29] Makhubela, B. C. E.; Jardine, A.; Smith, G. S. Green Chem. 2012, 14, 338.
[30] Baig, R. B. N.; Varma, R. S. Green Chem. 2013, 15, 1834.
[31] Shen, C.; Xu, J.; Yu, W.; Zhang P. Green Chem. 2014, 16, 3007.
[32] Collins, G.; Schmidt, M.; O'Dwyer, C.; McGlacken, G.; Holmes, J. ACS Catal. 2014, 4, 3105.
[33] Marcoux, J.; Doye, S.; Buchwald S. J. Am. Chem. Soc. 1997, 119, 10539.
[34] Takashi, M.; Fumitoshi, Y.; Masanori, S.; Kenji, K.; Hiroaki, S.; Masami, S.; Tsutomu, F. Synlett 2009, 2457.
[35] Li, Z.; Meng, F.; Zhang, J.; Xie, J.; Dai, B. Org. Biomol. Chem. 2016, 14, 10861.
[36] Janíkova, K.; Jedinak, L.; Volna, T.; Canka, P. Tetrahedron 2018, 74(5):606.
[37] Kantam, M. L.; Venkanna, G. T.; Sridhar, C.; Sreedhar, B.; Choudary, B. M. J. Org. Chem. 2006, 71, 9522.
[38] Zhang, Z. J.; Mao, J. C.; Zhu, D.; Wu, F.; Chen, H. L.; Wan, B. S. Tetrahedron 2006, 62, 4435.
[39] Zhang, X.; Xia, A.; Chen, H.; Liu, Y. Org. Lett. 2017, 19(8), 2118.
[40] Yin, W.; Wang, C.; Huang, Y. Org. Lett. 2013, 15(8), 1850.
[41] Hosseini-Sarvari, M.; Razmi Z. RSC Adv. 2014, 4, 44105.
[42] Shelke, G. M.; Rao, V. K.; Jha, M.; Cameron, T. S.; Kumar, A. Synlett. 2015, 26(3), 404.
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