Citation: Zihang Zhang,  Sizhe Li,  Liyan Kan,  Jun Wen,  Jiang Bian. 有机氟化物的电化学合成[J]. University Chemistry, ;2021, 36(12): 210200. doi: 10.3866/PKU.DXHX202102001 shu

有机氟化物的电化学合成

  • Corresponding author: Jiang Bian, bj@pku.edu.cn
  • Received Date: 1 February 2021

  • 有机氟化物在很多领域(尤其是药物方面)有着广泛的应用,但鉴于氟的特殊反应性,氟原子的引入一直是有机化学中的难题。而有机电化学合成作为近年来新兴的合成手段,大大拓宽了有机反应的界限,使得更多绿色简易的氟化方法被开发了出来。本文就将集中列举这些有机电化学方法氟化的实例,并探讨电化学方法对于氟化学这一领域可能的推动作用。
  • 加载中
    1. [1]

    2. [2]

      (a) Moissan, H. C. R. Hebd. Seances Acad. Sci. 1886, 102, 1534. (b) Moissan, H. C. R. Hebd. Seances Acad. Sci. 1886, 103, 202. (c) Moissan, H. C. R. Hebd. Seances Acad. Sci. 1886, 103, 256. (d) For some representative reports on fluorine and fluoride compounds, see:(i) Moissan, H. Ann. Chim. Phys. 1887, 12, 472.(ii) Moissan, H. Ann. Chim. Phys. 1891, 24, 224.(iii) Moissan, H. Ann. Chim. Phys. 1894, 2, 66.

    3. [3]

      Borodine, A. Ann. Chem. Pharm. 1863, 126, 58.

    4. [4]

      Elliott, A. J. Chlorofluorocarbons. In Organofluorine Chemistry:Principles and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C. Eds.; Plenum Press:New York, USA, 1994; pp. 145-157.

    5. [5]

      (a) Rhodes, R. The Making of the Atomic Bomb; Simon and Schuster:New York, USA, 1986. (b) Rhodes, R. Dark Sun:The Making of the Hydrogen Bomb; Simon and Schuster:New York, USA, 1995.

    6. [6]

      Simons, J. H. J. Electrochem. Soc. 1949, 95, 47.

    7. [7]

      Pearlson, W. H. J. Fluorine. Chem. 1986, 32, 29.

    8. [8]

      Fuchigami, T.; Inagi, S. Acc. Chem. Res. 2020, 53, 322.

    9. [9]

      Dinoiu, V.; Fukuhara, T.; Hara, S.; Yoneda, N. J. Fluor. Chem. 2000, 103, 75.

    10. [10]

      Berger, M.; Herszman, J. D.; Kurimoto, Y.; Kruijff, G. H. M.; Schuell, A.; Rufc, S.; Waldvogel, S. R. Chem. Sci. 2020, 11, 6053.

    11. [11]

      Xiang, J.; Shang, M.; Kawamata, Y.; Lundberg, H.; Reisberg, S. H.; Chen, M.; Mykhailiuk, P.; Beutner, G.; Collins, M. R.; Davies, A.; et al. Nature 2019, 573, 398.

    12. [12]

      Fukuhara, T.; Akiyama, Y.; Yoneda, N.; Tada, T.; Hara, S. Tetrahedron Lett. 2002, 43, 6583.

    13. [13]

      Tajima, T.; Nakajima, A.; Fuchigami, T. J. Org. Chem. 2006, 71, 1436.

    14. [14]

      Hou, Y.; Higashiya, S.; Fuchigami, T. J. Org. Chem. 1999, 64, 3346.

    15. [15]

      Fuchigami, T.; Inagi, S. Chem. Commun. 2011, 47, 10211.

    16. [16]

      Baba, D.; Ishii, H.; Higashiya, S.; Fujisawa, K.; Fuchigami, T. Tetrahedron 2001, 57, 9067.

    17. [17]

      Hasegaw, M.; Ishii, H.; Fuchigami, T. Green Chem. 2003, 5, 512.

    18. [18]

      Cao, Y.; Suzuki, K.; Tajima, T.; Fuchigami, T. Tetrahedron 2005, 61, 6854.

    19. [19]

      Hasegawa, M.; Ishii, H.; Fuchigami, T. Tetrahedron Lett. 2002, 43, 1503.

    20. [20]

      Suzuki, J.; Shida, N.; Inagi, S.; Fuchigami, T. Electroanalysis 2016, 28, 2797.

    21. [21]

      Fuchigami, T.; Tajima, T. J. Fluor. Chem. 2005, 126, 181.

    22. [22]

      Aoyama, M.; Fukuhara, T.; Hara, S. J. Org. Chem. 2008, 73, 4186.

    23. [23]

      (a) Schulz, L.; Waldvogel, S. R. Synlett 2019, 30, 275.(b) Bin, Y.; Inagi, S.; Fuchigami, T. Beilstein J. Org. Chem. 2015, 11, 85.(c) Sawamura, T.; Kuribayashi, S.; Inagi, S.; Fuchigami, T. Adv. Synth. Catal. 2010, 352, 2757.(d) Inagi, S.; Sawamura, T.; Fuchigami, T. Electrochem. Commun. 2008, 10, 1158.

    24. [24]

      Monoi, M.; Hara, S. J. Fluor. Chem. 2012, 140, 28.

    25. [25]

      Tajima, T.; Nakajima, A.; Doi, Y.; Fuchigami, T. Angew. Chem. Int. Ed. 2012, 51, 4413.

    26. [26]

      Sawamura, T.; Takahashi, K.; Inagi, S.; Fuchigami, T. Angew. Chem. Int. Ed. 2007, 46, 3550.

    27. [27]

      (a) Takahashi, K.; Furusawa, T.; Sawamura, T.; Kuribayashi, S.; Inagi, S.; Fuchigami, T. Electrochim. Acta 2012, 77, 47. (b) Sawamura, T.; Kuribayashi, S.; Inagi, S.; Fuchigama, T. Adv. Synth. Catal. 2010, 352, 2757. (c) Sawamura, T.; Kuribayashi, S.; Inagi, S.; Fuchigami, T. Org. Lett. 2010, 12, 644. (d) Fuchigami, T.; Sano, M. J. Electroanal. Chem. 1996, 414, 81.

    28. [28]

      Francke, R.; Little, R. D. Chem. Soc. Rev. 2014, 43, 2492.

    29. [29]

      Herszman, J. D.; Berger, M.; Waldvogel, S. R. Org. Lett. 2019, 21, 7893.

    30. [30]

      Fujita, T.; Fuchigami, T. Tetrahedron Lett. 1996, 37, 4725.

    31. [31]

      (a) Haupt, J. D.; Berger, M.; Waldvogel, S. R. Org. Lett. 2019, 21, 242. (b) Herszman, J. D.; Berger, M.; Waldvogel, S. R. Org. Lett. 2019, 21, 7893.

    32. [32]

      Fuchigami, T.; Tetsu, M.; Tajima, T.; Ishii, H. Synlett 2001, 8, 1269.

    33. [33]

      Fuchigami, T.; Mitomo, K.; Ishii, H.; Konno, A. J. Electroanal. Chem. 2001, 507, 30.

    34. [34]

      (a) Fukuzumi, S.; Kotani, H.; Ohkubo, K.; Ogo, S.; Tkachenko, N. V.; Lemmetyinen, H. J. Am. Chem. Soc. 2004, 126, 1600. (b) Ohkubo, K.; Mizushima, K.; Iwata, R.; Souma, K.; Suzukib, N.; Fukuzumi, S. Chem. Commun. 2010, 46, 601.

    35. [35]

      (a) Barham, J. P.; Kçnig, B. Angew. Chem. Int. Ed. 2020, 59, 11732. (b) Huang, H.; Strater, Z. M.; Rauch, M.; Shee, J.; Sisto, T. J.; Nuckolls, C.; Lambert, T. H. Angew. Chem. Int. Ed. 2019, 58, 13318. (c) Yan, H.; Hou, Z.; Xu, H. Angew. Chem. Int. Ed. 2019, 58, 4592.

    36. [36]

      Qiu, Y.; Scheremetjew, A.; Finger, L. H.; Ackermann, L. Chem. Eur. J. 2020, 26, 3241.

    37. [37]

      Margrey, A. K.; Nicewicz, D. A. Acc. Chem. Res. 2016, 49, 1997.

    38. [38]

      Dapperheld, S.; Steckhan, E.; Brinkhaus, K. G.; Esch, T. Chem. Ber. 1991, 124, 2557.

    39. [39]

      DFT Calculation is done by Gaussian09, in B3LYP/6-31G(d) level for optimization and freqency analysis, and wB97X-D/def2-TZVP level for single point energy:Gaussian 09, Revision D.01, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; et al. Gaussian, Inc.:Wallingford CT, 2013.

    40. [40]

      Sources of EOX data:(a) Schmidt, W.; Steckhan, E. Chem. Ber. 1980, 113, 577. (b) Steckhan, E. Organic Syntheses with Electrochemically Regenerable Redox Systems. In Electrochemistry I. Topics in Current Chemistry, Steckhan E. Eds.; Springer:Berlin, Heidelberg, Germany, 1987; p. 142.

    41. [41]

      Andreeva, V. N.; Grinberga, V. A.; Dedovb, A. G.; Loktevb, A. S.; Mayorovaa; N. A.; Moiseevb, I. I.; Stepanova, A. A. Russ. J. Electrochem. 2013, 49, 996.

    42. [42]

      Rodrigo, S.; Um, C.; Mixdorf, J. C.; Gunasekera, D; Nguyen, H. M.; Luo, L. Org. Lett. 2020, 22, 6719.

    43. [43]

      Khrizanforov, M.; Gryaznova, T.; Sinyashin, O.; Budnikova, Y. J. Organomet. Chem. 2012, 718, 101.

    44. [44]

      Dudkina, Y. B.; Mikhaylov, D. Y.; Gryaznova, T. V.; Sinyashin, O. G.; Vicic, D. A.; Budnikova, Y. H. Eur. J. Org. Chem. 2012, 11, 2114.

    45. [45]

      Dudkina, Y. B.; Khrizanforov, M. N.; Gryaznova, T. V.; Budnikova, Y. H. J. Organomet. Chem. 2014, 751, 301.

    46. [46]

      Takahira, Y.; Chen, M.; Kawamata, Y.; Mykhailiuka, P.; Nakamura, H.; Peters, B. K.; Reisberg, S. H.; Li, C.; Chen, L.; Hoshikawad, T.; et al. Synlett 2019, 30, 1178.

  • 加载中
    1. [1]

      Hong Yan Wenfeng Wang Keyin Ye Yaofeng Yuan . Organic Electrochemistry and Its Integration into Chemistry Teaching. University Chemistry, 2025, 40(5): 301-310. doi: 10.12461/PKU.DXHX202407027

    2. [2]

      Renxiu Zhang Xin Zhao Yunfei Zhang . Application of Electrochemical Synthesis in the Teaching of Organic Chemistry. University Chemistry, 2025, 40(4): 174-180. doi: 10.12461/PKU.DXHX202406116

    3. [3]

      Yongjian Zhang Fangling Gao Hong Yan Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035

    4. [4]

      Fengxiao Wang Zhiwei Miao Yaofeng Yuan . 有机磷化学与化学教学. University Chemistry, 2025, 40(8): 158-168. doi: 10.12461/PKU.DXHX202410077

    5. [5]

      Aidang Lu Yunting Liu Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029

    6. [6]

      Yinuo Wang Ziyu Liu Hongxia Tan Jun Tong Dazhen Xu . Synthesis of Bromobenzoxazine: Introduce a Comprehensive Organic Chemistry Experiment Transformed from Undergraduate Research Innovation. University Chemistry, 2025, 40(10): 208-216. doi: 10.12461/PKU.DXHX202411077

    7. [7]

      Shuhui Li Rongxiuyuan Huang Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028

    8. [8]

      Ruoyu Cao Jiaxin Chen Jiaen Hu Youting Zhai Jiacong Fu Lifen Hou Xuebin Yan Yanyang Li Kai Li Shuangquan Zang . Interactive Digital Experiment for Organic Synthesis: Designing Process and Case Presentation. University Chemistry, 2026, 41(1): 406-412. doi: 10.12461/PKU.DXHX202504022

    9. [9]

      Yifei Li Xuexin Chen Sihan Liu Shiyi Chen Ling Pan . Design and Application of Chemical Analysis Platform Based on Intelligent Integration of Big Data and Deep Learning Algorithm in Undergraduate Experimental Teaching. University Chemistry, 2026, 41(1): 169-178. doi: 10.12461/PKU.DXHX202504098

    10. [10]

      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

    11. [11]

      Tiantian MASumei LIChengyu ZHANGLu XUYiyan BAIYunlong FUWenjuan JIHaiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351

    12. [12]

      Lin′an CAODengyue MAGang XU . Research advances in electrically conductive metal-organic frameworks-based electrochemical sensors. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 1953-1972. doi: 10.11862/CJIC.20250160

    13. [13]

      Lu XUChengyu ZHANGWenjuan JIHaiying YANGYunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431

    14. [14]

      Jing SUBingrong LIYiyan BAIWenjuan JIHaiying YANGZhefeng Fan . Highly sensitive electrochemical dopamine sensor based on a highly stable In-based metal-organic framework with amino-enriched pores. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1337-1346. doi: 10.11862/CJIC.20230414

    15. [15]

      Shengbiao Zheng Liang Li Nini Zhang Ruimin Bao Ruizhang Hu Jing Tang . Metal-Organic Framework-Derived Materials Modified Electrode for Electrochemical Sensing of Tert-Butylhydroquinone: A Recommended Comprehensive Chemistry Experiment for Translating Research Results. University Chemistry, 2024, 39(7): 345-353. doi: 10.3866/PKU.DXHX202310096

    16. [16]

      Zhongyan Cao Youzhi Xu Menghua Li Xiao Xiao Xianqiang Kong Deyun Qian . Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes. University Chemistry, 2025, 40(4): 277-281. doi: 10.12461/PKU.DXHX202407017

    17. [17]

      Pan Li Huguo Shen Cong Hua Jinjie Fang Xiangying Chi Quan Jiang Zichen Feng Ye Kang Bin Zheng . Synthesis and Characterization of an Aggregation-Induced Emission-Active Organic Cage Molecule: A Proposed Comprehensive Chemistry Experiment. University Chemistry, 2025, 40(11): 337-345. doi: 10.12461/PKU.DXHX202502083

    18. [18]

      Yong Wang Yingying Zhao Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009

    19. [19]

      Shuai Yuan Yaofeng Yuan . Academician Chengye Yuan and Organic Phosphorus Chemistry. University Chemistry, 2025, 40(7): 393-400. doi: 10.12461/PKU.DXHX202409123

    20. [20]

      Ping LIGeng TANXin HUANGFuxing SUNJiangtao JIAGuangshan ZHUJia LIUJiyang LI . Green synthesis of metal-organic frameworks with open metal sites for efficient ammonia capture. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2063-2068. doi: 10.11862/CJIC.20250020

Metrics
  • PDF Downloads(17)
  • Abstract views(1947)
  • HTML views(388)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return