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

College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China

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。
- Electro-organic chemistry,
- Fluorochemistry,
- Organic synthesis,
- Methodology
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 E_OX 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.
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