Citation: Sun Xiaoli, Sun Zhenhua, Han Minmin, Han Jing, He Weimin, Chen Jie, Deng Hongmei, Shao Min, Zhang Hui, Cao Weiguo. Synthesis of Perfluoroalkylated Fluorenes with Phosphonate Group via One-Pot Synthesis Process[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 192-199. doi: 10.6023/cjoc201808028 shu

Synthesis of Perfluoroalkylated Fluorenes with Phosphonate Group via One-Pot Synthesis Process

Sun Xiaoli ^a ,
Sun Zhenhua ^a ,
Han Minmin ^b ,
Han Jing ^a ,
He Weimin ^a ,
Chen Jie ^a ,
Deng Hongmei ^c ,
Shao Min ^c ,
Zhang Hui ^a,c,, ,
Cao Weiguo ^a,d,e,,

a.
Department of Chemistry, Shanghai University, Shanghai 200444
b.
Qianweichang College, Shanghai University, Shanghai 200444
c.
Laboratory for Microstructures, Instrumental Analysis and Research Center of Shanghai University, Shanghai 200444
d.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
e.
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Zhang Hui, wgcao@staff.shu.edu.cn Cao Weiguo, wgcao@staff.shu.edu.cn
Received Date: 24 August 2018
Revised Date: 13 September 2018
Available Online: 19 January 2018
Fund Project: the National Natural Science Foundation of China 21672138Project supported by the National Natural Science Foundation of China (No. 21672138)

Figures(3)

A simple and versatile metal-free protocol for the synthesis of perfluoroalkyated fluorene derivatives bearing phosphonate group is achieved. The reactions proceeded via one-pot three-component condensation of indenones, fluorinated alkynylphosphonates and malononitrile under mild conditions. This protocol is highly regioselective, operationally facile and applicable to a variety of indenones in good to excellent yields.
- multicomponent reactions (MCRs),
- one-pot synthesis,
- perfluoroalkynyl phosphonate,
- fluorene
1. [1]
  For selected examples, see: (a) Pearce, A. K.; Rolfe, B. E.; Russell, P. J.; Tse, B. W. C.; Whittaker, A. K.; Fuchs, A. V.; Thurecht, K. J. Polym. Chem. 2014, 5, 6932.
  (b) Zeng, W.; Ballard, T. E.; Tkachenko, A. G.; Burns, V. A.; Feldheim, D. L.; Melander, C. Bioorg. Med. Chem. Lett. 2006, 16, 5148.
  (c) Beutler, U.; Fuenfschilling, P. C.; Steinkemper, A. Org. Process Res. Dev. 2007, 11, 341.
  (d) Hicks, L. D.; Hyatt, J. L.; Stoddard, S.; Tsurkan, L.; Edwards, C. C.; Wadkins, R. M.; Potter, P. M. J. Med. Chem. 2009, 52, 3742.
2. [2]
  For selected reviews, see: (a) Leclerc, M. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 2867.
  (b) Scherf, U.; List, E. J. W. Adv. Mater. 2002, 14, 477.
  (c) Grimsdale, A.; Mallen, K. Adv. Polym. Sci. 2006, 199, 1.
  (d) Monkman, A.; Rothe, C.; King, S.; Dias, F. Adv. Polym. Sci. 2008, 212, 187.
  (e) Knaapila, M.; Monkman, A. P. Adv. Mater. 2013, 25, 1090.
3. [3]
  Liu, B.; Yu, W.; Lai, Y.; Huang, W. Chem. Commun. 2000, 551.
4. [4]
  Zhang, F.; Mammo, W.; Andersson, L. Adv. Mater. 2006, 18, 2169. doi: 10.1002/(ISSN)1521-4095
5. [5]
  (a) Fleckenstein, C. A.; Plenio, H. Chem.-Eur. J. 2007, 13, 2701.
  (b) Bassas, O.; Huuskonen, J.; Rissanen, K.; Koskinen, A. M. P. Eur. J. Org. Chem. 2009, 1340.
  (c) Paleo, M. R.; Aurrecoechea, N.; Jung, K.-Y.; Rapoport, H. J. Org. Chem. 2003, 68, 130.
  (d) Ding, Y.; Wang, J.; Abboud, K. A.; Xu, Y.; Dolbier, W. R.; Richards, Jr., N. G. J. J. Org. Chem. 2001, 66, 6381.
6. [6]
  For recent selected examples, see: (a) Chinnagolla, R. K.; Jeganmohan, M. Org. Lett. 2012, 14, 5246.
  (b) Song, J.; Wei, F.; Sun, W.; Li, K.; Tian, Y.; Liu, C.; Li, Y.; Xie, L. Org. Lett. 2015, 17, 2106.
  (c) Sun, F.-L.; Zeng, M.; Gu, Q.; You, S.-L. Chem.-Eur. J. 2009, 15, 8709.
  (d) Peterson, J. J.; Simon, Y. C.; Coughlin, E. B.; Carter, K. R. Chem. Commun. 2009, 4950.
  (e) Shabashov, D.; Maldonado, J. R. M.; Daugulis, O. J. Org. Chem. 2008, 73, 7818.
  (f) Barluenga, J.; Trincado, M.; Rubio, E.; Gonz lez, J. M. Angew. Chem., Int. Ed. 2006, 45, 3140.
  (g) Wong, K.; Chi, L.; Huang, S.; Liao, Y.; Liu, Y.; Wang, Y. Org. Lett. 2006, 8, 5029.
  (h) Wang, S.-G.; Han, L.; Zeng, M.; Sun, F.-L.; Zhang, W.; You, S.-L. Org. Biomol. Chem. 2012, 10, 3202.
7. [7]
  For recent selected examples, see: (a) Janina, B.; Thomas, W.; Svenja, T.; Eleni, S.; David, A.; Matthias, R.; Frank, R.; Stephen, A.; Hashmi, K. Adv. Synth. Catal. 2017, 359, 225.
  (b) Xu, S.; Chen, R.; Fu, Z.-H.; Zhou, Q.; Zhang, Y.; Wang, J.-B. ACS Catal. 2017, 7, 1993.
  (c) Shi, G.-F.; Chen, D.-S.; Jiang, H.; Zhang, Y.; Zhang, Y.-H. Org. Lett. 2016, 18, 2958.
  (d) Peng, X.-P.; Luo, H.-W.; Wu, F.-H.; Zhu, D.-H.; Ganesan, A.; Huang, P.; Wen, S.-J. Adv. Synth. Catal. 2017, 359, 1152.
  (e) Song, J.; Sun, W.; Li, Y.-L.; Wei, F.-L.; Liu, C.; Qian, Y.; Chen, S.-F. Chem.-Asian J. 2016, 11, 211.
  (f) Song, J.; Li, Y.-L.; Sun, W.; Yi, C.-L.; Wu, H.; Wang, H.-T.; Ding, K.-R.; Xiao, K.; Liu, C. New J. Chem. 2016, 40, 9030.
  (g) Vergeiner, C.; Ulrich, M.; Li, C.; Liu, X.; Müller, T.; Krä utler, B. Chem.-Eur. J. 2015, 21, 1.
  (h) Zhou, A.-H.; Pan, F.; Zhu, C.; Ye, L.-W. Chem.-Eur. J. 2015, 21, 10278.
  (i) Song, J.; Sun, W.; Li, Y.; Wei, F.; Liu, C.; Qian, Y.; Chen, S. Chem.-Asian. J. 2016, 11, 211.
  (j) Zhou, A.-H.; Pan, F.; Zhu, C.; Ye, L.-W. Chem.-Eur. J. 2015, 21, 10278.
8. [8]
  For recent selected examples, see: (a) Shi, Z.; Glorius, F. Chem. Sci. 2013, 4, 829.
  (b) Wertz, S.; Leifert, D.; Studer, A. Org. Lett. 2013, 15, 928.
  (c) Seo, S.; Slater, M.; Greaney, M. F. Org. Lett. 2012, 14, 2650.
  (d) Lockner, J. W.; Dixon, D. D.; Risgaard, R.; Baran, P. S. Org. Lett. 2011, 13, 5628.
  (e) Chu, X.-Q.; Xing, Z.-H.; Meng, H.; Xu, X.-P.; Ji, S.-J. Org. Chem. Front. 2016, 3, 165.
9. [9]
  (a) Morimoto, K.; Itoh, M.; Hirano, K.; Satoh, T.; Shibata, Y.; Tanaka, K.; Miura, M. Angew. Chem., Int. Ed. 2012, 51, 5359.
  (b) Hsiao, C. C.; Lin, Y.-K.; Liu, C.-J.; Wu, T.-C.; Wu, Y.-T. Adv. Synth. Catal. 2010, 352, 3267.
  (c) Liu, Z.; Tan, H.; Wang, L.; Fu, T.; Xia, Y.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2015, 54, 3056.
  (d) Shi, Y.-B.; Gao, S.-H. Tetrahedron 2016, 72, 1717.
10. [10]
11. [11]
  Sun, Z.-H.; Huang, Q.; Han, J.; He, W.-M.; Chen, J.; Xu, Y.-C.; Deng, H.-M.; Shao, M.; Zhang, H.; Cao, W.-G. Tetrahedron 2018, 74, 2073. doi: 10.1016/j.tet.2018.03.012
12. [12]
  (a) Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology, John Wiley & Sons, Chichester, 2009.
  (b) Azema, L.; Baron, R.; Ladame, S. Curr. Enzyme Inhib. 2006, 2, 61.
  (c) Nagarajan, R.; Pratt, F. R. Biochemistry 2004, 43, 9664.
13. [13]
  CCDC 1862491(4a) contains all crystallographic details of this publication and are available free of charge at www.ccdc.cam.ac.uk/consts/retrieving.html. Or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ; fax: +441223336033; or deposit@ccdc.cam.ac.uk. Unit cell parameters (4a): a=0.7134(16) nm, b=1.146(3) nm, c=1.266(3) nm; α=106.91(3)°, β=98.99(3)°, g=91.87(3)°; space group: P-1.
14. [14]
  (a) Esmaeili, A.; Moradi, A.; Khoddam-Mohammadi, H. Tetrahedron 2010, 66, 3575.
  (b) Alizadeh, A.; Hosseini, S.; Sedighian, H.; Bayat, F.; Zhu, Z.; Dusek, M. Tetrahedron 2015, 71, 7885.
  (c) Su, W.; Ding, K.; Chen, Z. Tetrahedron Lett. 2009, 50, 636.
15. [15]
  Broman, S. L.; Brand, S. L.; Parker, C. R.; Petersen, M. A.; Tortzen, C. G.; Kadziola, A.; Kilsa, K.; Nielsen, M. B. ARKIVOC 2011, ix, 51.
16. [16]
  (a) Chambers, R. D.; Holling, D.; Sand-ford, G.; Batsanov, A. S.; Howard, J. A. K. J. Fluorine Chem. 2004, 125, 661.
  (b) Nichson, T. E. J. Org. Chem. 1988, 53, 3870.
1. [1]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
2. [2]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
3. [3]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
4. [4]
  Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095
5. [5]
  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
6. [6]
  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
7. [7]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
8. [8]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
9. [9]
  Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195
10. [10]
  . . Chinese Journal of Inorganic Chemistry, 2024, 40(11): 0-0.
11. [11]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
12. [12]
  Bingliang Li , Yuying Han , Dianyang Li , Dandan Liu , Wenbin Shang . One-Step Synthesis of Benorilate Guided by Green Chemistry Principles and in vivo Dynamic Evaluation. University Chemistry, 2024, 39(6): 342-349. doi: 10.3866/PKU.DXHX202311070
13. [13]
  Jiaojiao Yu , Bo Sun , Na Li , Cong Wen , Wei Li . Improvement of Classical Organic Experiment Based on the “Reverse-Step Optimization Method”: Taking Synthesis of Ethyl Acetate as an Example. University Chemistry, 2025, 40(3): 333-341. doi: 10.12461/PKU.DXHX202405177
14. [14]
  Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
15. [15]
  Yanting HUANG , Hua XIANG , Mei PAN . Construction and application of multi-component systems based on luminous copper nanoclusters. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2075-2090. doi: 10.11862/CJIC.20240196
16. [16]
  Bin HE , Hao ZHANG , Lin XU , Yanghe LIU , Feifan LANG , Jiandong PANG . Recent progress in multicomponent zirconium?based metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2041-2062. doi: 10.11862/CJIC.20240161
17. [17]
  Ruitong Zhang , Zhiqiang Zeng , Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004
18. [18]
  Shuying Zhu , Shuting Wu , Ou Zheng . Improvement and Expansion of the Experiment for Determining the Rate Constant of the Saponification Reaction of Ethyl Acetate. University Chemistry, 2024, 39(4): 107-113. doi: 10.3866/PKU.DXHX202310117
19. [19]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
20. [20]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(1100)
HTML views(176)

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