Cu(0)/Selectfluor体系催化的查尔酮的环氧化反应
收稿日期: 2015-07-17
修回日期: 2015-08-20
网络出版日期: 2015-08-26
基金资助
国家自然科学基金(Nos. 21172197, 21372201)、浙江工业大学"省重中之重一级学科"开放基金资助项目.
Cu(0)/Selectfluor System-Catalyzed Epoxidation of Chalcone Compounds
Received date: 2015-07-17
Revised date: 2015-08-20
Online published: 2015-08-26
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21172197, 21372201) and the Opening Foundation of Zhejiang Key Course of Chemical Engineering and Technology, Zhejiang University of Technology.
在Cu(0)/Selectfluor体系的作用下, 以水为氧源, 在温和的条件下实现了查尔酮的环氧化反应, 制得了2,3-环氧- 1,3-二芳基丙酮类化合物. 通过考察催化剂前体、氧化剂的种类与用量、溶剂等因素对反应的影响, 获得了最优的反应条件. 该反应普适性较好, 各种取代的查尔酮皆能顺利地进行环氧化反应, 并取得较高的收率, 最高可达92%.
关键词: 铜催化; Selectfluor; 查尔酮; 环氧化
张剑 , 汪衡 , 任少波 , 张文霞 , 刘运奎 . Cu(0)/Selectfluor体系催化的查尔酮的环氧化反应[J]. 有机化学, 2015 , 35(12) : 2650 -2654 . DOI: 10.6023/cjoc201507016
A mild synthesis of 1,3-diaryl-2,3-epoxypropanones via the Cu(0)/selectfluor system-catalyzed epoxidation of chalcone compounds has been achieved using water as the oxygen source. The optimized reaction conditions were established through systematic investigations of the effect of catalyst precursors, oxidants and their dosages, and solvents on the reaction conditions. A variety of chalcones with different substituted patterns can undergo the epoxidation smoothly and furnish products with high yields of up to 92%.
Key words: copper catalysis; selectluor; chalcone; epoxidation
[1] Lattanzi, A.; Russo, A. Tetrahedron 2006, 62, 12264.
[2] (a) Parker, R. E.; Isaucs, N. S. Chem. Rev. 1959, 59, 737. (b) Adger, B. M.; Barkley, J. V.; Bergeron, S.; Cappi, M. W.; Flowerdew, B. E.; Jackson, M. P.; McCague, R.; Nugent, T. C.; Rorberts, S. M. J. Chem. Soc., Perkin Trans. 1 1997, 3501. (c) Bhat, B. A.; Puri, S. C.; Qurishi, M. A.; Dhar, K. L.; Qazi, G. N. Synth. Commun. 2005, 35, 1135.
[3] (a) Yamaguchi, K.; Mori, K.; Mizugaki, K.; Ebitani, K.; Kaneda, K. J. Org. Chem. 2000, 65, 6897. (b) Porter, M. J.; Skidmore, J. Chem. Commun. 2000, 14, 1215.
[4] (a) Zhang, W.; Zhang, J.; Liu, Y. Synlett 2013, 24, 2709. (b) Zhang, J.; Wu, D.; Chen, X.; Liu, Y. J. Org. Chem. 2014, 79, 4799. (c) Zhang, J.; Wang, H.; Ren, S.; Zhang, W.; Liu, Y. Org. Lett.. 2015, 17, 2920.
[5] Gezegen, H.; Dingil, A.; Ceylan, M. J. Heterocycl. Chem., 2010, 47, 1017.
[6] Adam, W.; Hadjiarapoglou, L.; Smerz, A. Chem. Ber. 1991, 124, 227.
[7] Kumar, C. V.; Ramaiah, D.; Das, P. K.; George, M. V. J. Org. Chem. 1985, 50, 2818.
[8] Jin, H.; Zhao, H.; Zhao, F.; Li, S.; Liu, W.; Zhou, G.; Tao, K.; Hou, T. Ultrason. Sonochem. 2008, 16, 304.
[9] Xiang, M.; Ni, X.; Yi, X., Zheng, A.; Wang, W.; He, M.; Xiong, J.; Liu, T.; Ma, Y.; Zhu, P.; Zheng, X.; Tang, T. ChemCatChem 2015, 7, 521.
[10] Krohnke, F.; Schulze, A. Ber. Dtsch. Chem. Ges. B 1939, 72B, 2000.
[11] Lakouraj, M. M.; Movassagh, B.; Bahrami, K. Synth. Commun. 2001, 31, 1239.
[12] Li, J.-L.; Liu, X.-F.; Yin, Y.; Du, C. Org. Commun. 2009, 2, 1.
[13] Li, J.; Liu, X.; Liu, X.; Li, L. Chin. J. Org. Chem. 2008, 28, 2162 (in Chinese). (李记太, 刘献锋, 刘晓茹, 李玲, 有机化学, 2008, 28, 2162.)
[14] Zolfigol, M. A.; Chehardoli, G.; Shiri, M. React. Funct. Polym. 2007, 67, 723.
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