L-酪氨酸修饰的石墨烯铜催化含氮杂环化合物的N-芳基化反应
收稿日期: 2015-04-19
修回日期: 2015-06-18
网络出版日期: 2015-07-10
基金资助
国家自然科学基金(No. 21303139)资助项目.
L-Tyrosine-Grafted Graphene Copper for Catalyzing N-Arylation of Nitrogen Heterocycles
Received date: 2015-04-19
Revised date: 2015-06-18
Online published: 2015-07-10
Supported by
Project supported by the National Natural Science Foundation of China (No. 21303139).
周丽梅 , 郎文成 , 蒋晓慧 , 黄强 , 尹梦云 . L-酪氨酸修饰的石墨烯铜催化含氮杂环化合物的N-芳基化反应[J]. 有机化学, 2015 , 35(11) : 2340 -2346 . DOI: 10.6023/cjoc201504028
The catalytic performance of L-tyrosine-grafted graphene copper (Tyr-G-Cu) was investigated in the N-arylation of nitrogen heterocycles. In the presence of this catalyst, the N-arylation proceeded smoothly and afforded the desired coupling products with good yields, respectively. Meanwhile, the catalyst was reused five times without remarkable loss of activity. Finally, the plausible heterogeneous recycle process of catalyst was identified by typical hot filtration test.
Key words： L-tyrosine; graphene; copper catalysts; N-arylation; heterogeneous catalysis
[1] Kiruthika, S.; Perumal, P. Org. Lett. 2014, 16, 484.
[2] Xi, L.; Zhang, R.; Liang, S.; Chen, S.; Yu, X. Org. Lett. 2014, 16, 5269.
[3] Petiot, P.; Dansereau, J.; Gagnon, A. RSC Adv. 2014, 4, 22255.
[4] Morofuji, T.; Shimizu, A.; Yoshida, J. J. Am. Chem. Soc. 2014, 136, 4496.
[5] Yang, C.; Fu, Y.; Huang, Y.; Yi, J.; Guo, Q.; Liu, L. Angew. Chem., Int. Ed. Engl. 2009, 48, 7398.
[6] Qin, J.; Chen, F.; Ding, Z.; He, Y.; Xu, L.; Fan, Q. Org. Lett. 2011, 13, 6568.
[7] Cai, Q.; Zhou, F. Synlett 2012, 408.
[8] Wolf, C.; Boswell, M.; Yeung, F. Synlett 2012, 1240.
[9] Wang, Y.; Wu, Z.; Wang, L.; Li, Z.; Zhou, X. Chem. Eur. J. 2009, 15, 8971.
[10] Li, Z.; Wu, Z.; Deng, H.; Zhou, X. Chin. J. Org. Chem. 2013, 33, 760 (in Chinese).(李正凯, 吴之清, 邓 杭, 周向葛, 有机化学, 2013, 33, 760.)
[11] Evano, G.; Blanchard, N.; Toummi, M. Chem. Rev. 2008, 108, 3054.
[12] Hartwig, J. Acc. Chem. Res. 2008, 41, 1534.
[13] Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450.
[14] Chen, Y.; Xie, X.; Ma, D. J. Org. Chem. 2007, 72, 9329.
[15] Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
[16] Moussa, S.; Siamaki, A.; Gupton, B.; El-Shall, M. ACS Catal. 2012, 2, 145.
[17] Shaabani, A.; Mahyari, M. J. Mater. Chem. A 2013, 1, 9303.
[18] Tan, R.; Li, C.; Luo, J.; Kong, Y.; Zheng, W.; Yin, D. J. Catal. 2013, 298, 138.
[19] Yuan, D.; Chen, B. Chin. J. Org. Chem. 2014, 34, 1630 (in Chinese). (袁定重, 陈碧波, 有机化学, 2014, 34, 1630.)
[20] Keßler, M.; Robke, S.; Prechtl, M. Catal. Sci. Technol. 2013, 4, 102.
[21] Pai, G.; Chattopadhyay, A. Tetrahedron Lett. 2014, 55, 941.
[22] Cheng, Y.; Sun, L. Chin. J. Org. Chem. 2013, 33, 877 (in Chinese). (成宜娟, 孙丽萍, 有机化学, 2013, 33, 877.)
[23] Mondal, P.; Sinha, A.; Salam, N.; Roy, A.; Jana, N.; Islam, S. M. RSC Adv. 2013, 3, 5615.
[24] Movahed, S.; Dabiri, M.; Bazgir, A. Appl. Catal., A 2014, 481, 79.
[25] Huang, Q.; Zhou, L.; Jiang, X.; Zhou, Y.; Fan, H.; Lang, W. ACS Appl. Mater. Interfaces 2014, 6, 13502.
[26] Zhang, P.; Yuan, J.; Li, H.; Liu, X.; Xu, X.; Antoniettib, M.; Wang, Y. RSC Adv. 2013, 3, 1890.
[27] Kim, A. Y.; Lee, H. J.; Park, J. C.; Kang, H.; Yang, H.; Song, H.; Park, K. H. Molecules 2009, 14, 5169.
[28] Joseph, P. J.; Priyadarshini, S.; Kantam, M.; Maheswaran, H. Catal. Sci. Technol. 2011, 1, 234.
[29] Rout, L.; Jammi, S.; Punniyamurthy T. Org. Lett. 2007, 9, 3397.
[30] Collins, G.; Schmidt, M.; O'Dwyer, C.; McGlacken, G.; Holmes, J. ACS Catal. 2014, 4, 3105.
[31] Movahed, S.; Esmatpoursalmani, R.; Bazgir, A. RSC Adv. 2014, 4, 14586.
[32] Lv, X.; Bao, W. J. Org. Chem. 2007, 72, 3863.
[33] Zhang, J.; Yin, H.; Han, S. Chin. J. Org. Chem. 2012, 32, 1429 (in Chinese). (张敬先, 殷慧清, 韩世清, 有机化学, 2012, 32, 1429.)
[34] Choudary, B.; Sridhar, C.; Kantam, M.; Venkanna, G.; Sreedhar, B. J. Am. Chem. Soc. 2005, 127, 9948.
[35] Yang, M.; Liu, F. J. Org. Chem. 2007, 72, 8969.
[36] Cheng, D.; Gan, F.; Qian, W.; Bao, W. Green Chem. 2008, 10, 171.
[37] Rout, L.; Jammi, S.; Punniyamurthy. T. Org. Lett. 2007, 17, 3397.
[38] Ziegler, D.; Choi, J.; Muñoz-Molina, J.; Bissember, A.; Peters, J.; Fu, G. J. Am. Chem. Soc. 2013, 135, 13107.
/
| 〈 |
|
〉 |
