Citation: Gu Yingchun, Huang You. Tributylphosphine Catalyzed Cross Rauhut-Currier Reaction of Chalcones and Acrylates[J]. Chinese Journal of Organic Chemistry, ;2019, 39(8): 2251-2256. doi: 10.6023/cjoc201904017 shu

Tributylphosphine Catalyzed Cross Rauhut-Currier Reaction of Chalcones and Acrylates

Gu Yingchun ^a,b ,
Huang You ^a,,

a.
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071
b.
School of Science, Tianjin Chengjian University, Tianjin 300384

Corresponding author: Huang You, hyou@nankai.edu.cn
Received Date: 8 April 2019
Revised Date: 4 May 2019
Available Online: 15 August 2019
Fund Project: the National Natural Science Foundation of China 21472097the National Natural Science Foundation of China 21672109the National Natural Science Foundation of China 21871148the Natural Science Foundation of Tianjin City 15JCYBJC20000Project supported by the National Natural Science Foundation of China (Nos. 21672109, 21871148, 21472097) and the Natural Science Foundation of Tianjin City (No. 15JCYBJC20000)

Figures(1)

Rauhut-Currier (RC) reaction is an effective atom-economic method to construct C-C bond. However, the application of this reaction is limited by the lack of selectivity. Herein, an efficient intermolecular cross Rauhut-Currier reaction between chalcones and acrylates in the presence of the tributylphosphine catalyst was developed, the reactions were carried out in mild conditions, and performed well with a series of substrates, delivering the desired products with acceptable to good yields.
- tributylphosphine,
- catalysis,
- Rauhut-Currier reaction,
- chalcone,
- acrylate
1. [1]
  (a) Ni, H.; Chan, W.-L.; Lu, Y. Chem. Rev. 2018, 118, 9344.
  (b) Guo, H.; Fan, Y.-C.; Sun, Z.; Wu, Y.; Kwon, O. Chem. Rev. 2018, 118, 10049.
2. [2]
  Rauhut, M.; Currier, H. US 3074999, 1963[Chem. Abstr. 1963, 58, 1124a].
3. [3]
  (a) Aroyan, C. E.; Dermenci, A.; Miller, S. J. Tetrahedron 2009, 65, 4069.
  (b) Xie, P.; Huang, Y. Eur. J. Org. Chem. 2013, 6213.
4. [4]
  Morita, K.; Kobayashi, T. Bull. Chem. Soc. Jpn. 1969, 42, 2732. doi: 10.1246/bcsj.42.2732
5. [5]
  McClure, J. D. J. Org. Chem. 1970, 35, 3045. doi: 10.1021/jo00834a039
6. [6]
  (a) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402.
  (b) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404.
7. [7]
  (a) Aroyan, C. E.; Miller, S. J. J. Am. Chem. Soc. 2007, 129, 256.
  (b) Gong, J.-J.; Li, T.-Z.; Pan, K.; Wu, X.-Y. Chem. Commun. 2011, 47, 1491.
  (c) Zhang, X.-N.; Shi, M. Eur. J. Org. Chem. 2012, 6271.
  (d) Takizawa, S.; Tue, M. N. N.; Grossmann, A.; Enders, D.; Sasai, H. Angew. Chem., Int. Ed. 2012, 51, 5423.
  (e) Su, X.; Zhou, W.; Li, Y.; Zhang, J. Angew. Chem., Int. Ed. 2015, 54, 6874.
  (d) Jin, H.; Zhang, Q.; Li, E.; Jia, P.; Li, N.; Huang, Y. Org. Biomol. Chem. 2017, 15, 7097.
8. [8]
  Dong, X.; Liang, L.; Li, E.; Huang, Y. Angew. Chem., Int. Ed. 2015, 54, 1621. doi: 10.1002/anie.201409744
9. [9]
  Zhou, W.; Su, X.; Tao, M.; Zhu, C.; Zhao, Q.; Zhang, J. Angew. Chem., Int. Ed. 2015, 54, 14853. doi: 10.1002/anie.201508108
10. [10]
  (a) Zhao, Q.-Y.; Pei, C.-K.; Guan, X.-Y.; Shi, M. Adv. Synth. Catal. 2011, 353, 1973.
  (b) Zhou, W.; Chen, P.; Tao, M.; Su, X.; Zhao, Q.; Zhang, J. Chem. Commun. 2016, 52, 7612.
  (c) Qin, C.; Liu, Y.; Yu, Y.; Fu, Y.; Li, H.; Wang, W. Org. Lett. 2018, 20, 1304.
11. [11]
  (a) Xie, P.; Huang, Y.; Lai, W.; Meng, X.; Chen, R. Org. Biomol. Chem. 2011, 9, 6707.
  (b) Ma, J.; Xie, P.; Hu, C.; Huang, Y.; Chen, R. Chem.-Eur. J. 2011, 17, 7418.
  (c) Hu, C.; Geng, Z.; Ma, J.; Huang, Y.; Chen, R. Chem.-Asian J. 2012, 7, 2032.
  (d) Hu, C.; Zhang, Q.; Huang, Y. Chem.-Asian J. 2013, 8, 1981.
1. [1]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . Catalytic Effect of H₃PW₁₂O₄₀ on Hydrogen Storage of MgH₂. Acta Physico-Chimica Sinica, 2025, 41(1): 100001-0. doi: 10.3866/PKU.WHXB202308032
2. [2]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
3. [3]
  Xiaogang Liu , Mengyu Chen , Yanyan Li , Xiantao Ma . Experimental Reform in Applied Chemistry for Cultivating Innovative Competence: A Case Study of Catalytic Hydrogen Production from Liquid Formaldehyde Reforming at Room Temperature. University Chemistry, 2025, 40(7): 300-307. doi: 10.12461/PKU.DXHX202408007
4. [4]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
5. [5]
  Peng XU , Shasha WANG , Nannan CHEN , Ao WANG , Dongmei YU . Preparation of three-layer magnetic composite Fe₃O₄@polyacrylic acid@ZiF-8 for efficient removal of malachite green in water. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 544-554. doi: 10.11862/CJIC.20230239
6. [6]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
7. [7]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 2408015-0. doi: 10.3866/PKU.WHXB202408015
8. [8]
  Zijian Zhao , Yanxin Shi , Shicheng Li , Wenhong Ruan , Fang Zhu , Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094
9. [9]
  Yajin Li , Huimin Liu , Lan Ma , Jiaxiong Liu , Dehua He . Photothermal Synthesis of Glycerol Carbonate via Glycerol Carbonylation with CO₂ over Au/Co₃O₄-ZnO Catalyst. Acta Physico-Chimica Sinica, 2024, 40(9): 2308005-0. doi: 10.3866/PKU.WHXB202308005
10. [10]
  Xingyang LI , Tianju LIU , Yang GAO , Dandan ZHANG , Yong ZHOU , Meng PAN . A superior methanol-to-propylene catalyst: Construction via synergistic regulation of pore structure and acidic property of high-silica ZSM-5 zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1279-1289. doi: 10.11862/CJIC.20240026
11. [11]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
12. [12]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
13. [13]
  Jinghua Wang , Yanxin Yu , Yanbiao Ren , Yesheng Wang . Integration of Science and Education: Investigation of Tributyl Citrate Synthesis under the Promotion of Hydrate Molten Salts for Research and Innovation Training. University Chemistry, 2024, 39(11): 232-240. doi: 10.3866/PKU.DXHX202402057
14. [14]
  Hui-Ying Chen , Hao-Lin Zhu , Pei-Qin Liao , Xiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046
15. [15]
  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
16. [16]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
17. [17]
  Xiaohang JIN , Qi LIU , Jianping LANG . Room‑temperature solid‑state synthesis, structure, and third‑order nonlinear optical properties of phosphine‑ligand‑protected silver thiolate clusters. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1505-1512. doi: 10.11862/CJIC.20250125
18. [18]
  Xuyu WANG , Xinran XIE , Dengke CAO . Photoreaction characteristics and luminescence modulation in phosphine-anthracene-based Au(Ⅰ) and Ir(Ⅲ) complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1513-1522. doi: 10.11862/CJIC.20250113
19. [19]
  Heng Zhang . Determination of All Rate Constants in the Enzyme Catalyzed Reactions Based on Michaelis-Menten Mechanism. University Chemistry, 2024, 39(4): 395-400. doi: 10.3866/PKU.DXHX202310047
20. [20]
  Xichen YAO , Shuxian WANG , Yun WANG , Cheng WANG , Chuang ZHANG . Oxygen reduction performance of self?supported Fe/N/C three-dimensional aerogel catalyst layers. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1387-1396. doi: 10.11862/CJIC.20240384

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(709)
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