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
有机氟化物的电化学合成
English
有机氟化物的电化学合成
-
Key words:
- Electro-organic chemistry
- / Fluorochemistry
- / Organic synthesis
- / Methodology
-
-
[1]
Kirsh, P. 现代有机氟化学——合成、反应、应用. 第2版. 北京:化学工业出版社, 2014:7.
-
[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.(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]
Borodine, A. Ann. Chem. Pharm. 1863, 126, 58.Borodine, A. Ann. Chem. Pharm. 1863, 126, 58.
-
[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.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]
(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.(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]
Simons, J. H. J. Electrochem. Soc. 1949, 95, 47.Simons, J. H. J. Electrochem. Soc. 1949, 95, 47.
-
[7]
Pearlson, W. H. J. Fluorine. Chem. 1986, 32, 29.Pearlson, W. H. J. Fluorine. Chem. 1986, 32, 29.
-
[8]
Fuchigami, T.; Inagi, S. Acc. Chem. Res. 2020, 53, 322.Fuchigami, T.; Inagi, S. Acc. Chem. Res. 2020, 53, 322.
-
[9]
Dinoiu, V.; Fukuhara, T.; Hara, S.; Yoneda, N. J. Fluor. Chem. 2000, 103, 75.Dinoiu, V.; Fukuhara, T.; Hara, S.; Yoneda, N. J. Fluor. Chem. 2000, 103, 75.
-
[10]
Berger, M.; Herszman, J. D.; Kurimoto, Y.; Kruijff, G. H. M.; Schuell, A.; Rufc, S.; Waldvogel, S. R. Chem. Sci. 2020, 11, 6053.Berger, M.; Herszman, J. D.; Kurimoto, Y.; Kruijff, G. H. M.; Schuell, A.; Rufc, S.; Waldvogel, S. R. Chem. Sci. 2020, 11, 6053.
-
[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.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]
Fukuhara, T.; Akiyama, Y.; Yoneda, N.; Tada, T.; Hara, S. Tetrahedron Lett. 2002, 43, 6583.Fukuhara, T.; Akiyama, Y.; Yoneda, N.; Tada, T.; Hara, S. Tetrahedron Lett. 2002, 43, 6583.
-
[13]
Tajima, T.; Nakajima, A.; Fuchigami, T. J. Org. Chem. 2006, 71, 1436.Tajima, T.; Nakajima, A.; Fuchigami, T. J. Org. Chem. 2006, 71, 1436.
-
[14]
Hou, Y.; Higashiya, S.; Fuchigami, T. J. Org. Chem. 1999, 64, 3346.Hou, Y.; Higashiya, S.; Fuchigami, T. J. Org. Chem. 1999, 64, 3346.
-
[15]
Fuchigami, T.; Inagi, S. Chem. Commun. 2011, 47, 10211.Fuchigami, T.; Inagi, S. Chem. Commun. 2011, 47, 10211.
-
[16]
Baba, D.; Ishii, H.; Higashiya, S.; Fujisawa, K.; Fuchigami, T. Tetrahedron 2001, 57, 9067.Baba, D.; Ishii, H.; Higashiya, S.; Fujisawa, K.; Fuchigami, T. Tetrahedron 2001, 57, 9067.
-
[17]
Hasegaw, M.; Ishii, H.; Fuchigami, T. Green Chem. 2003, 5, 512.Hasegaw, M.; Ishii, H.; Fuchigami, T. Green Chem. 2003, 5, 512.
-
[18]
Cao, Y.; Suzuki, K.; Tajima, T.; Fuchigami, T. Tetrahedron 2005, 61, 6854.Cao, Y.; Suzuki, K.; Tajima, T.; Fuchigami, T. Tetrahedron 2005, 61, 6854.
-
[19]
Hasegawa, M.; Ishii, H.; Fuchigami, T. Tetrahedron Lett. 2002, 43, 1503.Hasegawa, M.; Ishii, H.; Fuchigami, T. Tetrahedron Lett. 2002, 43, 1503.
-
[20]
Suzuki, J.; Shida, N.; Inagi, S.; Fuchigami, T. Electroanalysis 2016, 28, 2797.Suzuki, J.; Shida, N.; Inagi, S.; Fuchigami, T. Electroanalysis 2016, 28, 2797.
-
[21]
Fuchigami, T.; Tajima, T. J. Fluor. Chem. 2005, 126, 181.Fuchigami, T.; Tajima, T. J. Fluor. Chem. 2005, 126, 181.
-
[22]
Aoyama, M.; Fukuhara, T.; Hara, S. J. Org. Chem. 2008, 73, 4186.Aoyama, M.; Fukuhara, T.; Hara, S. J. Org. Chem. 2008, 73, 4186.
-
[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.(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]
Monoi, M.; Hara, S. J. Fluor. Chem. 2012, 140, 28.Monoi, M.; Hara, S. J. Fluor. Chem. 2012, 140, 28.
-
[25]
Tajima, T.; Nakajima, A.; Doi, Y.; Fuchigami, T. Angew. Chem. Int. Ed. 2012, 51, 4413.Tajima, T.; Nakajima, A.; Doi, Y.; Fuchigami, T. Angew. Chem. Int. Ed. 2012, 51, 4413.
-
[26]
Sawamura, T.; Takahashi, K.; Inagi, S.; Fuchigami, T. Angew. Chem. Int. Ed. 2007, 46, 3550.Sawamura, T.; Takahashi, K.; Inagi, S.; Fuchigami, T. Angew. Chem. Int. Ed. 2007, 46, 3550.
-
[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.(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]
Francke, R.; Little, R. D. Chem. Soc. Rev. 2014, 43, 2492.Francke, R.; Little, R. D. Chem. Soc. Rev. 2014, 43, 2492.
-
[29]
Herszman, J. D.; Berger, M.; Waldvogel, S. R. Org. Lett. 2019, 21, 7893.Herszman, J. D.; Berger, M.; Waldvogel, S. R. Org. Lett. 2019, 21, 7893.
-
[30]
Fujita, T.; Fuchigami, T. Tetrahedron Lett. 1996, 37, 4725.Fujita, T.; Fuchigami, T. Tetrahedron Lett. 1996, 37, 4725.
-
[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.(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]
Fuchigami, T.; Tetsu, M.; Tajima, T.; Ishii, H. Synlett 2001, 8, 1269.Fuchigami, T.; Tetsu, M.; Tajima, T.; Ishii, H. Synlett 2001, 8, 1269.
-
[33]
Fuchigami, T.; Mitomo, K.; Ishii, H.; Konno, A. J. Electroanal. Chem. 2001, 507, 30.Fuchigami, T.; Mitomo, K.; Ishii, H.; Konno, A. J. Electroanal. Chem. 2001, 507, 30.
-
[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.(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]
(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.(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]
Qiu, Y.; Scheremetjew, A.; Finger, L. H.; Ackermann, L. Chem. Eur. J. 2020, 26, 3241.Qiu, Y.; Scheremetjew, A.; Finger, L. H.; Ackermann, L. Chem. Eur. J. 2020, 26, 3241.
-
[37]
Margrey, A. K.; Nicewicz, D. A. Acc. Chem. Res. 2016, 49, 1997.Margrey, A. K.; Nicewicz, D. A. Acc. Chem. Res. 2016, 49, 1997.
-
[38]
Dapperheld, S.; Steckhan, E.; Brinkhaus, K. G.; Esch, T. Chem. Ber. 1991, 124, 2557.Dapperheld, S.; Steckhan, E.; Brinkhaus, K. G.; Esch, T. Chem. Ber. 1991, 124, 2557.
-
[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.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]
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.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]
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.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]
Rodrigo, S.; Um, C.; Mixdorf, J. C.; Gunasekera, D; Nguyen, H. M.; Luo, L. Org. Lett. 2020, 22, 6719.Rodrigo, S.; Um, C.; Mixdorf, J. C.; Gunasekera, D; Nguyen, H. M.; Luo, L. Org. Lett. 2020, 22, 6719.
-
[43]
Khrizanforov, M.; Gryaznova, T.; Sinyashin, O.; Budnikova, Y. J. Organomet. Chem. 2012, 718, 101.Khrizanforov, M.; Gryaznova, T.; Sinyashin, O.; Budnikova, Y. J. Organomet. Chem. 2012, 718, 101.
-
[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.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]
Dudkina, Y. B.; Khrizanforov, M. N.; Gryaznova, T. V.; Budnikova, Y. H. J. Organomet. Chem. 2014, 751, 301.Dudkina, Y. B.; Khrizanforov, M. N.; Gryaznova, T. V.; Budnikova, Y. H. J. Organomet. Chem. 2014, 751, 301.
-
[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.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.
-
[1]
-
扫一扫看文章
计量
- PDF下载量: 19
- 文章访问数: 2418
- HTML全文浏览量: 481

下载: