Citation: Yang Siqi, Li Xin, Peng Zhuojin, Yu Wenyan, Wang Guangxu, Jin Yalan, Zheng Bingbing, Dai Hongxue, Bai Dachang. Synthesis of Pentafluoroethylated Pyridines via Cu-Catalyzed[3+3] Cycloaddition Reaction of Oxime Acetates[J]. Chinese Journal of Organic Chemistry, ;2019, 39(6): 1623-1629. doi: 10.6023/cjoc201902025 shu

Synthesis of Pentafluoroethylated Pyridines via Cu-Catalyzed[3+3] Cycloaddition Reaction of Oxime Acetates

Henan Key Laboratory of Organic Functional Molecule and Drug Innovation, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007

Corresponding author: Bai Dachang, baidachang@126.com
Received Date: 23 February 2019
Revised Date: 16 May 2019
Available Online: 28 June 2019
Fund Project: the Start-Up Fund from Henan Normal University qd17108the National Natural Science Foundation of China 21801067the Research Fund from Henan Normal University 5101034011009Project supported by the National Natural Science Foundation of China (No. 21801067), the Research Fund from Henan Normal University (No. 5101034011009), the Natural Science Research Program of Education Department of Henan Province (No. 18A150010), and the Start-Up Fund from Henan Normal University (No. qd17108)the Natural Science Research Program of Education Department of Henan Province 18A150010

Figures(3)

An improved method for the synthesis of pentafluoroethylated pyridines through Cu-catalyzed[3+3] cyclo-addition reaction of oxime acetates is reported. The starting materials are more readily available, and these reactions occurred under mild conditions with broad substrate scope and excellent regioselectivity. Mechanistic studies have also been preformed.
- pentafluoroethylated,
- pyridines,
- copper-catalyzed,
- oxime acetates
1. [1]
  (a) Wong, D. T.; Perry, K. W.; Bymaster, F. P. Nat. Rev. Drug Discovery 2005, 4, 764.
  (b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
  (c) Hagmann, W. K. J.Med. Chem. 2008, 51, 4359.
  (d) O'Hagan, D. J. Fluorine Chem.2010, 131, 1071.
  (e) Meanwell, N. A. J. Med. Chem. 2011, 54, 2529.
  (f) Wang, J.; Sánchez-Roselló, M.; Aceñ a, J.; Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
2. [2]
  For selected reports/reviews: (a) Varela, J. A.; Saa, C. Chem. Rev. 2003, 103, 3787.
  (b) Manning, J. R.; Davies, H. M. L. J. Am. Chem. Soc. 2008, 130, 8602.
  (c) Zard, S. Z. Chem. Soc. Rev. 2008, 37, 1603.
  (d) Wang, Y.-F.; Chiba, S. J. Am. Chem. Soc. 2009, 131, 12570.
  (e) Ackermann, L. Chem. Rev. 2011, 111, 1315.
  (f) McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885.
  (g) Kumar, P.; Prescher, S.; Louie, J. Angew. Chem., Int. Ed. 2011, 50, 10694.
  (h) Too, P. C.; Noji, T.; Lim, Y. J.; Li, X.; Chiba, S. Synlett 2011, 2789.
  (i) Chinnagolla, R. K.; Pimparkar, S.; Jeganmohan, M. Org. Lett. 2012, 14, 3032.
  (j) Pi, C.; Cui, X.-L.; Liu, X.-Y.; Guo, M-X.; Zhang, H.-Y.; Wu, Y.-J. Org. Lett. 2014, 16, 5164.
  (k) Huang, H.-W.; Ji, X.-C.; Wu, W.-Q.; Jiang, H.-F. Chem. Soc. Rev. 2015, 44, 1155.
  (l) Xu, Y.; Hu, W.; Tang, X.; Zhao, J.; Wu, W.; Jiang, H. Chem. Commun. 2015, 51, 6843.
  (m) Zhao, M.-N.; Ren, Z.-H.; Yu, L.; Wang, Y.-Y.; Guan, Z.-H. Org. Lett. 2016, 18, 1194.
  (n) Hille, T.; Irrgang, T.; Kempe, R. Angew. Chem., Int. Ed. 2017, 56, 371.
3. [3]
  (a) Shevchenko, N. E.; Nenajdenko, V. G.; Röschenthaler, G.-V. J. Fluorine Chem. 2008, 129, 390.
  (b) Prakash, G. K. S.; Wang, Y.; Mogi, R.; Hu, J.-B.; Mathew, T.; Olah, G. A. Org. Lett. 2010, 12, 2932.
  (c) Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475. (d) Mu, X; Chen, S. J, ; Zhen, X. L.; Liu, G. S. Chem.-Eur. J. 2011, 17, 6039.
  (d) Liu, T.; Shen, Q. Org. Lett. 2011, 13, 2342.
  (e) Zhang, C. P.; Wang, Z. L.; Chen, Q. Y.; Zhang, C. T.; Gu, Y. C.; Xiao, J. C. Angew. Chem., Int. Ed. 2011, 50, 1896.
  (f) Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214.
  (g) Chu, L. L.; Qing, F. L. Acc. Chem. Res. 2014, 47, 1513.
  (h) Landelle, G.; Panossian, A.; Pazenok, S.; Vors, J.-P.; Leroux, F. R. Beilstein J. Org. Chem. 2013, 9, 2476.
  (i) Yu, Y. B.; Wang, Z.; Zhang, X. G. Sci. China Chem. 2014, 57, 276.
  (j) Shao, X.-X.; Xu, C.-F.; Lu, L.; Shen, Q. Acc. Chem. Res. 2015, 48. 1227.
  (k) Rong, J.; Deng, Li.; Tan, P.; Ni, C. F; Gu, Y. C.; Hu, J. B. Angew. Chem., Int. Ed. 2016, 55, 274.
  (l) Ni, C. F.; Hu, M. Y.; Hu, J. B. Chem. Rev. 2015, 115, 765.
  (m) Feng, Z.; Xiao, Y. L.; Zhang, X. G. Acc. Chem. Res., 2018, 51, 2264.
  (n) Wang, F.; Chen, P. H.; Liu, G. S. Acc. Chem. Res. 2018, 51, 2036.
  (o) Yang, B.; Yu, D. H.; Xu, X. H.; Qing, F. L. ACS Catal. 2018, 8, 2839.
4. [4]
  (a) Langlois, B. R.; Roques, N. J. Fluorine Chem. 2007, 128, 1318.
  (b) Kremlev, M. M.; Tyrra, W.; Mushta, A. I.; Naumann, D.; Yaguposkii, Y. L. J. Fluorine Chem. 2010, 131, 212.
  (c) Popov, I.; Lindeman, S.; Daugulis, O. J. Am. Chem. Soc. 2011, 133, 9286.
  (d) Serizawa, H.; Aikawa, K.; Mikami, K. Org. Lett. 2014, 16, 3456.
5. [5]
  Yagupoi'skii, L. M.; II'chenko, A. Y.; Kondratenko, N. V. Russ. Chem. Rev. 1974, 43, 32. doi: 10.1070/RC1974v043n01ABEH001787
6. [6]
  (a) Kobayashi, Y. J. Chem. Soc., Perkin Trans. 1 1980, 661.
  (b) Wiermers, D. M.; Burton, D. J. J. Am. Soc. Chem. 1986, 108, 832.
  (c) Urata, H.; Fuchikami, T. Tetrahedron Lett. 1991, 32, 91.
  (d) Carr, G. E.; Chambers, R. D.; Holmes, T. F.; Parker, D. G. J. Chem. Soc., Perkin Trans. 1 1988, 921.
7. [7]
  (a) Litvinas, N. D.; Fier, P. S.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 536.
  (b) Mormino, M. G.; Fier, P. S.; Hartwig, J. F. Org. Lett. 2014, 16, 1744.
8. [8]
  (a) Lishchynskyi, A.; Grushin, V. V. J. Am. Chem. Soc. 2013, 135, 12584.
  (b) Serizawa, H.; Aikawa, K.; Mikami, K. Org. Lett. 2014, 16, 3456.
9. [9]
  (a) Lin, Q.-Y.; Xu, X.-H.; Qing, F.-L. J. Org. Chem. 2014, 79, 10434.
  (b) Zhu, J. S.; Li, Y. G.; Ni, C. F.; Shen, Q. L. Chin. J. Chem. 2016, 34, 662.
  (c) Liu, Y. F.; Ge, H.M.; Lu, L.; Shen, Q. L. Chin. J. Org. Chem. 2019, 39, 257.
10. [10]
  Xie, Q. Q.; Li, L. C.; Zhu, Z. Y.; Zhang, R. Y.; Ni, C. F.; Hu, J. B. Angew. Chem., Int. Ed. 2018, 57, 13211. doi: 10.1002/anie.201807873
11. [11]
  Bai, D. C.; Wang, X. L.; Zheng, G. F.; Li, X. W. Angew. Chem., Int. Ed. 2018, 57, 6633. doi: 10.1002/anie.v57.22
12. [12]
  (a) Tang, X.-D.; Huang, L.-B.; Qi, C.-R.; Wu, W.-Q.; Jiang, H.-F. Chem. Commun. 2013, 49, 9597.
  (b) Ran, L.-F.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Green Chem. 2014, 16, 112.
  (c) Du, W.; Zhao, M.-N.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Chem. Commun. 2014, 50, 7437.
  (d) Faulkner, A.; Race, N. J.; Scott, J. S.; Bower, J. F. Chem. Sci. 2014, 5, 2416.
  (e) Zhu, C.-L.; Zeng, H.; Chen, F.-L.; Liu, C.; Zhu, R.; Wu, W.-Q.; Jiang, H.-F. Org. Chem. Front. 2018, 5, 571.
  (f) Tang, X. D.; Wu, W. Q.; Zeng, W.; Jiang, H. F. Acc. Chem. Res. 2018, 51, 1092.
1. [1]
  Pengzi Wang , Wenjing Xiao , Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090
2. [2]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
3. [3]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
4. [4]
  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
5. [5]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
6. [6]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
7. [7]
  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
8. [8]
  Jiapei Zou , Junyang Zhang , Xuming Wu , Cong Wei , Simin Fang , Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081
9. [9]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
10. [10]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
11. [11]
  Qiaowen CHANG , Ke ZHANG , Guangying HUANG , Nuonan LI , Weiping LIU , Fuquan BAI , Caixian YAN , Yangyang FENG , Chuan ZUO . Syntheses, structures, and photo-physical properties of iridium phosphorescent complexes with phenylpyridine derivatives bearing different substituting groups. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 235-244. doi: 10.11862/CJIC.20240311
12. [12]
  Hongjie SHEN , Haozhe MIAO , Yuhe YANG , Yinghua LI , Deguang HUANG , Xiaofeng ZHANG . Synthesis, crystal structure, and fluorescence properties of two Cu(Ⅰ) complexes based on pyridyl ligand. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 855-863. doi: 10.11862/CJIC.20250009
13. [13]
  Xue Dong , Xiaofu Sun , Shuaiqiang Jia , Shitao Han , Dawei Zhou , Ting Yao , Min Wang , Minghui Fang , Haihong Wu , Buxing Han . 碳修饰的铜催化剂实现安培级电流电化学还原CO₂制C₂₊产物. Acta Physico-Chimica Sinica, 2025, 41(3): 2404012-. doi: 10.3866/PKU.WHXB202404012
14. [14]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
15. [15]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
16. [16]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
17. [17]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
18. [18]
  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
19. [19]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
20. [20]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(748)
HTML views(81)

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