综述与进展

电化学催化下的多氟烷基化反应研究进展

  • 刘颖杰 ,
  • 韩莹徽 ,
  • 林立青 ,
  • 许颖
展开
  • 1 哈尔滨商业大学药学院 哈尔滨 150076

收稿日期: 2020-09-11

  修回日期: 2020-09-22

  网络出版日期: 2020-10-15

基金资助

哈尔滨商业大学青年后备人才(2019CX36)

Research Progress of Polyfluoroalkylation Reaction under Electrochemical Catalysis

  • Yingjie Liu ,
  • Yinghui Han ,
  • Liqing Lin ,
  • Ying Xu
Expand
  • 1 School of Pharmacy, Harbin University of Commerce, Harbin 150076
* Corresponding author. E-mail:

Received date: 2020-09-11

  Revised date: 2020-09-22

  Online published: 2020-10-15

Supported by

Youth Reserve Talent Project of Harbin Business University(2019CX36)

摘要

氟化学已经在各行各业受到广泛应用, 氟化学和有机化学的结合也遍地生花. 由于将氟原子或氟基团引入到药物中具有重要意义, 因此寻求一种有效的氟烷基化途径至关重要. 随着电化学的发展, 人们将电化学和氟烷基化反应进行了巧妙地结合. 进而得到了更加安全、经济、环保并且高效的氟烷基化途径. 在电化学指导下的氟烷基化反应途径, 不仅在反应方式方面进行了革新, 同样在底物普适性方面也具有优势. 针对不饱和脂肪族化合物及其衍生物和芳香族化合物的电化学催化下的氟烷基化反应已经有诸多报道. 根据底物的性质及其反应机理总结了电催化下氟烷基化方法的进展.

本文引用格式

刘颖杰 , 韩莹徽 , 林立青 , 许颖 . 电化学催化下的多氟烷基化反应研究进展[J]. 有机化学, 2021 , 41(3) : 934 -946 . DOI: 10.6023/cjoc202008017

Abstract

Fluorine chemistry has been widely used in all walks of life, and the combination of fluorine chemistry and organic chemistry is blooming everywhere. Since the introduction of fluorine atoms or fluorine groups into drugs is of great significance, it is essential to seek an effective fluoroalkylation pathway. With the development of electrochemistry, people combine electrochemistry and fluoroalkylation reaction skillfully. In turn, a safer, more economical, environmentally friendly and efficient fluoroalkylation pathway is obtained. The fluoroalkylation reaction pathway under the guidance of electrochemistry has not only reformed the reaction method, but also has advantages in terms of substrate universality. Fluoroalkylation of unsaturated aliphatic compounds their derivatives and aromatic compounds under electrochemical catalysis has been reported. According to the nature of the substrate and its reaction mechanism, the progress of electrocatalytic fluoroalkylation methods is summarized.

参考文献

[1]
He, S. C.; Tian, D. Z.; Guo, B. H.; Chen, H. C. Zhejiang Chem. Ind. 2014, 45, 1. (in Chinese)
[1]
(何双材, 田端正, 郭本辉, 陈慧闯, 浙江化工, 2014, 45, 1.)
[2]
Kochervinskii, V. V.; Shoranova, L. O.; Shakirzyanov, R. I. Pharm. Sci. Technol. Today 2016,27266.
[3]
Tomilenko, A. A.; Bul'bak, T. A.; Pokhilenko, L. N. Dokl. Akad. Nauk 2016, 469, 82.
[4]
Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
[5]
Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
[6]
Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305.
[7]
Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
[8]
Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475.
[9]
Zhou, Y.; Wang, J.; Gu, Z, N.; Wang, S. N.; Zhu, W. Chem. Rev. 2016, 116, 422.
[10]
Wang, J.; Sanchez-Roselló, M.; Acen?, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
[11]
(a) Li, G. B.; Zhang, C.; Song, C.; Ma, Y. D. Beilstein J. Org. Chem. 2018, 14, 155.
[11]
(b) Alonso, C.; Marigorta, E. M.; Rubiale, G.; Palacios, F. Chem. Rev. 2015, 115, 1847.
[11]
(c) Studer, A. Angew. Chem.. Int. Ed. 2012, 51, 8950.
[12]
(a) Nagib, D. A.; MacMillan, D. W. Nature 2011, 480, 224.
[12]
(b) Ji, Y.; Brueckl, T.; Baxter, R.; Baxter, R. D.; Fujiwara, Y.; Seiple, I. B.; Su, S.; Blackmond, D. G.; Baran, P. S. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 14411.
[12]
(c) Brien, A. G.; Maruyama, A.; Inokuma, Y.; Fujita, M.; Baran, P. S.; Blackmond, D. G. Angew. Chem.. Int. Ed. 2014, 53, 11868.
[13]
(a) Sladojevich, F.; McNeill, E.; Borgel, J.; Zheng, S. L.; Ritter, T. Angew. Chem.. Int. Ed. 2015, 54, 3712.
[13]
(b) Cui, L.; Matusaki, Y.; Tada, N.; Miura, T.; Uno, B.; Itoh, A. Adv. Synth. Catal. 2013, 355, 2203.
[14]
Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679.
[15]
(a) Oishi, M.; Kondo, H.; Amii, H. Chem. Commun. 2009,1909.
[15]
(b) Shimizu, R.; Egami, H.; Nagi, T.; Chae, J.; Hamashima, Y.; Sodeoka, M. Tetrahedron Lett. 2010, 51, 5947.
[15]
(c) Liu, T.; Shen, Q. Org. Lett. 2011, 13, 2342.
[15]
(d) Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034.
[16]
(a) Sawada, H.; Nakayama, M.; Yoshida, T. J. Fluorine Chem. 1990, 46, 423.
[16]
(b) Langlois, B. R.; Laurent, E.; Roidot, N. Tetrahedron Lett. 1991, 32, 7525.
[16]
(c) Kino, T.; Nagase, Y.; Ohtsuka, Y.; Yamamoto, K.; Uraguchi, D.; Tokuhisa, K.; Yamakawa, T. J. Fluorine Chem. 2010, 131, 98.
[17]
Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648.
[18]
He, L.; Natte, K.; Rabeah, J.; Taeschler, C.; Neumann, H.; Bruckner, A.; Beller, M. Angew. Chem., Int. Ed. 2015, 54, 4320.
[19]
Mohle, S.; Zirbes, M.; Rodrigo, E.; Gieshoff, T.; Wiebe, A.; Waldvogel, S. R. Angew. Chem., Int. Ed. 2018, 57, 6018.
[20]
Frontana-Uribe, B. A.; Little, R. D.; Ibanez, J. G.; Palma, A.; Vasquez-Medrano, R. Green Chem. 2010, 12, 2099.
[21]
Moeller, K. D. Tetrahedron 2000, 56, 9527.
[22]
Sperry, J. B.; Wright, D. L. Chem. Soc. Rev. 2006, 35, 605.
[23]
(a) Yoshida, J.-I.; Kataoka, K.; Horcajada, R.; Nagaki, A. Chem. Rev. 2008, 108, 2265.
[23]
(b) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230.
[24]
Herzog, G. Chromatographia 2016, 79, 521.
[25]
Zhang, Y.; Petersen, J. L.; Milsmann, C. J. Am. Chem. Soc. 2016, 138, 13115.
[26]
Yeung, K. T.; To, W. P.; Sun, C.; Cheng, G.; Ma, C.; Tong, G. S. M.; Yang, C.; Che, C. M. Angew. Chem., Int. Ed. 2017, 56, 133.
[27]
Gazi, S.; Ng, W. K. H.; Ganguly, R.; Moeljadi, A. M. P.; Hirao, H.; Soo, H. S. Chem. Sci. 2015, 6, 7130.
[28]
Uneyama, K. Tetrahedron 1991, 47, 555.
[29]
Arai, K.; Watts, K.; Wirth, T. ChemistryOpen 2013, 3, 23.
[30]
Jud, W.; Kappe, C. O.; Cantillo, D. Chem.-Eur. J. 2018, 24, 17234.
[31]
Gregory, S. S.; Lin, S. ACS Catal. 2018, 8, 5175.
[32]
Zhang, L. L.; Zhang, G. T.; Wang, P.; Li, Y. L.; Lei, A. W. Org. Lett. 2018, 20, 7396.
[33]
Guan, Z. P.; Wang, H. M.; Huang, Y. G.; Wang, Y. K.; Wang, S. C.; Lei, A. W. Org. Lett. 2019, 21, 4619.
[34]
Sun, X.; Ma, H. X.; Mei, T. S.; Fang, P.; Hu, Y. L. Org. Lett. 2019, 21, 3167.
[35]
Zou, Z. L.; Zhang, W. G.; Wang, Y.; Kong, L. Y.; Karotsis, G.; Wang, Y. Org. Lett. 2019, 21, 1857.
[36]
(a) Zhang, Y. C.; Han, X. L.; Zhao, J. Q.; Qian, Z. J.; Li, T. M.; Tang, Y. Q.; Zhang, H. Y. Adv. Synth. Catal. 2018, 360, 2659.
[36]
(b) Wu, Z.; Wang, D. P.; Liu, Y.; Huan, L. T.; Zhu, C. J. Am. Chem. Soc. 2017, 139, 1388.
[36]
(c) Ye, K. Y.; Pombar, G.; Fu, N. K.; Sauer, G. S.; Keresztes, I.; Lin, S. J. Am. Chem. Soc. 2018, 140, 2438.
[36]
(d) Sauer, G. S.; Lin, S. ACS Catal. 2018, 8, 5175.
[36]
(e) Yang, Y. D.; Lwamoto, K.; Tokunaga, E.; Shibata, N. Chem. Commun. 2013, 49, 5510.
[36]
(f) Sakamoto, R.; Kashiwagi, H.; Selvakumar, S.; Moteki, S.; Maruoka, K. Org. Biomol. Chem. 2016, 14, 6417.
[37]
Wang, H.; Xu, Q.; Yu, S. Y. Org. Chem. Front. 2018, 5, 2224.
[38]
Jung, H. I.; Kim, Y.; Kim, Y. D. Org. Biomol. Chem. 2019, 17, 25.
[39]
(a) Wu, Q. Y.; Ao, G. Z. Org. Chem. Front. 2018, 5, 2061.
[39]
(b) Ye, K. Y.; Pombar, N. F.; Sauer, G. S.; Keresztes, I.; Lin, S. J. Am. Chem. Soc. 2018, 140, 2438.
[39]
(c) Jiang, Y. Y.; Dou, G. Y.; Xu, K.; Zeng, C. C. Org. Chem. Front. 2018, 5, 2573.
[39]
(d) Ye, K. Y.; Song, Z.; Sauer, S.; Harenberg, H.; Fu, N.; Lin, S. Chem.-Eur. J. 2018, 24, 12274.
[39]
(e) Jud, W.; Kappe, C. O.; Cantillo, D. Chem.-Eur. J. 2018, 24, 17234.
[39]
(f) Zhang, L.; Zhang, G.; Wang, Y.; Lei, A. Org. Lett. 2018, 20, 7396.
[39]
(g) Yingchao, J. W.; Guillot, D. R.; Kouklovsky, C.; Vencent, G. J. Am. Chem. Soc. 2019, 141, 2831.
[39]
(h) Zhang, Z.; Zhang, Y.; Cao, F. L.; Bai, G.; Yang, Y.; Mo, F. Org. Lett. 2019, 21, 761.
[39]
(i) Ruan, Z.; Huang, Z.; Xu, Z.; Tian, M. X.; Yu, X. Y.; Ackermann, L. Org. Lett. 2019, 21, 1237.
[40]
Li, Z.; Jiao, L. C.; Sun, Y. H.; He, Z. Y.; Wei, Z. L.; Liao, W. W. Angew. Chem. 2020, 132, 7333.
[41]
(a) Majumdar, K. C.; Mondal, S. Chem. Rev. 2011, 111, 7749.
[41]
(b) Iwanrjko, J.; Wojaczynska, E. Org. Biomol. Chem. 2018, 16, 7296.
[42]
Dhanak, D.; Duffy, K. J.; Johnston, V. K.; Goerke, J. L.; Darcy, M.; Shaw, A. N.; Gu, B.; Silverman, C.; Gates, A. T.; Nonnemacher, M. R.; Earnshaw, D. L.; Casper, D. J.; Kaura, A.; Baker, A.; Greenwood, C.; Gutshall, L. L.; Maley, D.; Delvecchio, A.; Ricardo, M.; Hofmann, G. A.; Alnoah, Z.; Cheng, H. Y.; Chan, G.; Khandekar, S.; Keenan, R. M.; Sarisky, R. T. J. Biol. Chem. 2002, 277, 38322.
[43]
(a) Zheng, J.; Zhang, D. Y.; Cui, S. Adv. Synth. Catal. 2016, 358, 746.
[43]
(b) Chen, D.; Ji, M.; Zhu, C. Chem. Commun. 2019, 55, 7796.
[44]
Kang, J. C.; Tu, Y. Q.; Dong, J. W.; Chen, C.; Zhou, J.; Ding, T. M.; Zai, J. T.; Chen, Z. M.; Zhang, S. Y. Org. Lett. 2019, 21, 2536.
[45]
Zhang, Z. X.; Zhang, L.; Cao, Y.; Li, F.; Bai, G. C.; Liu, G. Q.; Yang, Y.; Mo, F. Y. Org. Let. 2019, 21, 762.
[46]
Xiong, P.; Xu, H. H.; Song, J. S.; Xu, H. C. J. Am. Chem. Soc. 2018, 140, 2460.
[47]
(a) Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8950.
[47]
(b) Ni, C. F.; Hu, M. Y.; Hu, J. B. Chem. Rev. 2015, 115, 765.
[47]
(c) Alonso, C.; Marigorta, E. M.; Rubiales, G.; Palacios, F. Chem. Rev. 2015, 115, 1847.
[47]
(d) Belhomme, M. C.; Besset, T.; Poisson, T.; Pannecoucke, X. Chem.-Eur. J. 2015, 21, 12836.
[47]
(e) Rong, J.; Ni, C. F.; Hu, J. B. J. Org. Chem. 2017, 6, 139.
[48]
Taniguchi, T.; Idota, A.; Ishibashi, H. Org. Biomol. Chem. 2011, 9, 3151.
[49]
Zhang, S.; Li, L. J.; Zhang, J. J.; Xue, M. Y.; Xu, K. Chem. Sci. 2019, 10, 3181.
[50]
Li, F. Y.; lin, D. Z.; He, T. J.; Zhong, W. Q.; Huang, J. M. ChemCatChem 2019, 119, 2350.
[51]
Zhao, Y.; Lai, Y. L.; Du, K. S.; Lin, D. Z.; Huang, J. M. J. The J. Org. Chem. 2017, 82, 9655.
[52]
(a) Huang, J. M.; Lin, Z. Q.; Chen, D. S. Org. Lett. 2011, 141, 22.
[52]
(b) Gong, M.; Huang, J. M. Chem.-Eur. J. 2016, 22, 14293.
[52]
(c) Huang, H. B.; Huang, J. M. Adv. Synth. Catal. 2016, 358, 1975.
[52]
(d) Lai, Y. L.; Huang, J. M. Org. Lett. 2017, 19, 2022.
[52]
(e) Du, K. S.; Huang, J. M. Org. Lett. 2018, 20, 2911.
[52]
(f) Lin, D. Z.; Huang, J. M. Org. Lett. 2018, 20, 2112.
[52]
(g) Lai, Y. L.; Ye, J. S.; Huang, J. M. Chem.-Eur. J. 2016, 22, 5425.
[52]
(h) He, T. J.; Ye, Z.; Ke, Z.; Huang, J. M. Nat. Commun. 2019, 10, 833.
[53]
Brien, A. G. O.; Inokuma, M. Y.; Fujita, M.; Baran, P. S.; Blackmond, D. G. Angew. Chem. 2014, 53, 11868.
[54]
Qian, P.; Bi, M.; Su, J.; Zha, Z.; Wang, Z. J. Org. Chem. 2016, 81, 4876.
[55]
Dudkina, Y. B.; Khrizanforov, M. N.; Gryazonova, T. V.; Budnikova, Y. H. J. Organomet. Chem. 2014, 751, 301.
[56]
Dubinina, G. G.; Brennessel, W. W.; Miller, J. L.; Vicic, D. A. Organometallics 2008, 27, 3933.
[57]
Hossain, M. J.; Ono, T.; Wakiya, K.; Hisaeda, Y. J. Chem. Commun. 2017, 53, 10878.
[58]
Cui, L. X.; Ono, T.; Morita, Y.; Hisaede, Y. Dalton Trans. 2020, 22, 7546.
[59]
Jud, W.; Maljuric, S.; Kappe, C. O.; Cantillo, D. Org. Lett. 2019, 21, 7970.
[60]
Rodrigo, S.; Um, C.; Mixdorf, J. C.; Gunasekera, D.; Nguyen, H. M.; Luo, L. Org. Lett. 2020, 22, 6719.
[61]
Brien, A. G. O.; Inokuma, M.Y. Fujita, M.; Baran, P. S.; Blackmond, D. G. Angew. Chem. 2014, 53, 11868.
[62]
Beryl, J. R.; Raj, X. J. Orient. J. Chem. 2018, 34, 2098.
[63]
Dou, G. Y.; Jiang, Y. Y.; Xu, K.; Zeng, C. C. Org. Chem. Front. 2019, 6, 2392.
[64]
Jiang, Y. Y.; Dou, G. Y.; Xu, K.; Zeng, C. C. Org. Chem. Front. 2018, 5, 2573.
文章导航

/