Citation: Zhao Haiying, Yin Fengnan, Yu Lingyan, Li Baoguo, Bian Zhanxi. Facile Synthesis of Ferrocenylchalcone Promoted by Ionic Liquid or Phase-Transfer Catalyst[J]. Chinese Journal of Organic Chemistry, ;2016, 36(5): 1118-1121. doi: 10.6023/cjoc201511045 shu

Facile Synthesis of Ferrocenylchalcone Promoted by Ionic Liquid or Phase-Transfer Catalyst

1.
Inner Mongolia Key Laboratory of Fine Organic Synthesis, College of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021

Corresponding author: Zhao Haiying, hyzhao@imu.edu.cn Bian Zhanxi, bzx1957@sina.com
Received Date: 25 November 2015
Revised Date: 14 December 2015

Fund Project: Project supported by the National Natural Science Foundation of China No. 21562032and the Natural Science Foundation of Inner Mongolia Nos. 2013MS0207, 2014JQ02the Research Program of Science and Technology at Universities of Inner Mongolia No. NJZZ001

The Claisen-Schmidt condensation of acetylferrocene with arylaldehydes in the presence of ionic liquids (ILs) or phase-transfer catalysts (PTCs) provided the corresponding ferrocenylchalcones in high yields, and PTCs can promote the condensation reaction better than those of ILs. Optimum conditions were as follows: molar ratio of acetylferrocene, arylaldehyde, n-Bu₄NPF₆ and NaOH is 1:1:2.5:0.75, and the appropriate reaction temperature is 35 ℃ in anhydrous EtOH.
- ferrocene,
- chalcone,
- ionic liquid,
- phase-transfer catalyst,
- Claisen-Schmidt condensation
1. [1]
2. [2]
  Zhao, H.; Zhu, X.; Wang, D.; Chen, S.; Bian, Z. Aust. J. Chem. 2015, 68, 1035.
3. [3]
  Avila, H.; Smania, E.; Monache, F.; Junior, A. Bioorg. Med. Chem. 2008, 16, 9790.
4. [4]
  Niu, C.; Li, G.; Tuerxuntayi, A.; Aisa, H. A. Chin. J. Chem. 2015, 33, 486.
5. [5]
  Prasath, R.; Bhavana, P.; Ng, S. W.; Tiekink, E. R. T. J. Organomet. Chem. 2013, 726, 62.
6. [6]
  Attar, S.; O'Brien, Z.; Alhaddad, H.; Golden, M. L.; Calderón-Urrea, A. Bioorg. Med. Chem. 2011, 19, 2055.
7. [7]
  Wu, X.; Tiekink, E. R. T.; Kostetski, I.; Kocherginsky, N.; Tan, A. L. C.; Khoo, S. B.; Wilairat, P.; Go, M. L. Eur. J. Pharm. Sci. 2006, 27, 175.
8. [8]
9. [9]
  Yang, J. M.; Ji, S. J.; Gu, D. G.; Shen, Z. L.; Wang, S. Y. J. Organomet. Chem. 2005, 690, 2989.
10. [10]
  Parveen, H.; Hayat, F.; Salahuddin, A.; Azam, A. Eur. J. Med. Chem. 2010, 45, 3497.
11. [11]
  Gong, Z. L.; Xie, Y. S; Zhao, B. X.; Lv, H. S.; Liu, W. Y.; Zheng, L. W.; Lian, S. J. Fluoresc. 2011, 21, 355.
12. [12]
  Bukhari, S. N. A.; Jasamai, M.; Jantan, I.; Ahmad, W. Mini-Rev. Org. Chem. 2013, 10, 73.
13. [13]
  Fang, D.; Cheng, J.; Fei, Z.; Gong, K.; Liu, Z. Catal. Commun. 2008, 9, 1924.
14. [14]
  Shibata, K.; Katsuyama, I.; Matsui, M.; Muramatsu, H. Bull. Chem. Soc. Jpn. 1990, 63, 3710.
15. [15]
  Erasmus, E. Inorg. Chim. Acta 2011, 378, 95.
16. [16]
  Abashev, G. G.; Antuf'eva, A. D.; Bushueva, A. Y.; Kudryavtsev, P. G.; Osorgina, I. V.; Syutkin, R. V.; Shklyaeva, E. V. Russ. J. Appl. Chem. 2010, 83, 1435.
17. [17]
  Muller, T. J.; Conradie, J.; Erasmus, E. Polyhedron 2012, 33, 257.
18. [18]
  Srivastava, Y. K. Rasayan J. Chem. 2008, 1, 884.
19. [19]
  Liu, Y. T.; Lian, G. D.; Yin, D. W.; Su, B. J. Res. Chem. Intermed. 2012, 38, 1043.
20. [20]
  Liu, Y. T.; Feng, L.; Yin, D. W. Res. Chem. Intermed. 2013, 39, 2971.
21. [21]
  Ji, S. J.; Wang, S. Y.; Shen, Z. L.; Zhou, M. F. Chin. Chem. Lett. 2003, 14, 1246.
22. [22]
  Liu, W.; Xu, Q.; Chen, B.; Ma, Y. Synth. Commun. 2002, 32, 171.
23. [23]
  Salisova, M.; Puciova, M.; Postnov, U. N.; Toma, S. Chem. Papers 1990, 44, 201.
24. [24]
  Villemin, D.; Martin, B.; Puciova, M.; Toma, S. J. Organomet. Chem. 1994, 484, 27.
1. [1]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . 碳基催化剂催化有机液体氢载体脱氢研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-. doi: 10.1016/j.actphy.2024.100044
2. [2]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
3. [3]
  Juntao Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-. doi: 10.3866/PKU.WHXB202312024
4. [4]
  Xiuyun Wang , Jiashuo Cheng , Yiming Wang , Haoyu Wu , Yan Su , Yuzhuo Gao , Xiaoyu Liu , Mingyu Zhao , Chunyan Wang , Miao Cui , Wenfeng Jiang . Improvement of Sodium Ferric Ethylenediaminetetraacetate (NaFeEDTA) Iron Supplement Preparation Experiment. University Chemistry, 2024, 39(2): 340-346. doi: 10.3866/PKU.DXHX202308067
5. [5]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
6. [6]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
7. [7]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
8. [8]
  Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . 二维共价有机框架作为光催化剂在有机合成中的研究进展. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-. doi: 10.1016/j.actphy.2025.100086
9. [9]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
10. [10]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
11. [11]
  Xinxin YU , Yongxing LIU , Xiaohong YI , Miao CHANG , Fei WANG , Peng WANG , Chongchen WANG . Photocatalytic peroxydisulfate activation for degrading organic pollutants over the zero-valent iron recovered from subway tunnels. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 864-876. doi: 10.11862/CJIC.20240438
12. [12]
  Yuyao Wang , Zhitao Cao , Zeyu Du , Xinxin Cao , Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-. doi: 10.3866/PKU.WHXB202406014
13. [13]
  Fangxuan Liu , Ziyan Liu , Guowei Zhou , Tingting Gao , Wenyu Liu , Bin Sun . Hollow structured photocatalysts. Acta Physico-Chimica Sinica, 2025, 41(7): 100071-. doi: 10.1016/j.actphy.2025.100071
14. [14]
  Yi Yang , Xin Zhou , Miaoli Gu , Bei Cheng , Zhen Wu , Jianjun Zhang . Femtosecond transient absorption spectroscopy investigation on ultrafast electron transfer in S-scheme ZnO/CdIn₂S₄ photocatalyst for H₂O₂ production and benzylamine oxidation. Acta Physico-Chimica Sinica, 2025, 41(6): 100064-. doi: 10.1016/j.actphy.2025.100064
15. [15]
  Liuyun Chen , Wenju Wang , Tairong Lu , Xuan Luo , Xinling Xie , Kelin Huang , Shanli Qin , Tongming Su , Zuzeng Qin , Hongbing Ji . Soft template-induced deep pore structure of Cu/Al₂O₃ for promoting plasma-catalyzed CO₂ hydrogenation to DME. Acta Physico-Chimica Sinica, 2025, 41(6): 100054-. doi: 10.1016/j.actphy.2025.100054
16. [16]
  Hong LI , Xiaoying DING , Cihang LIU , Jinghan ZHANG , Yanying RAO . Detection of iron and copper ions based on gold nanorod etching colorimetry. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 953-962. doi: 10.11862/CJIC.20230370
17. [17]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
18. [18]
  Li'na ZHONG , Jingling CHEN , Qinghua ZHAO . Synthesis of multi-responsive carbon quantum dots from green carbon sources for detection of iron ions and L-ascorbic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 709-718. doi: 10.11862/CJIC.20240280
19. [19]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
20. [20]
  Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO₂ reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(677)
HTML views(95)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142