电化学合成氨基酸类化合物的研究进展
收稿日期: 2021-02-23
修回日期: 2021-04-07
网络出版日期: 2021-04-25
基金资助
国家自然科学基金(21761132021)
Electrochemical Approaches for Preparation of Tailor-Made Amino Acids
Received date: 2021-02-23
Revised date: 2021-04-07
Online published: 2021-04-25
Supported by
National Natural Science Foundation of China(21761132021)
氨基酸类化合物在现代医药化学研究和药物设计开发方面具有非常重要的作用, 一直以来, 开发高效的合成方法学来制备这些氨基酸类化合物的研究吸引了化学家们广泛的研究兴趣. 另一方面, 近些年电化学反应逐渐兴起成为一种绿色可再生的合成手段, 是有机合成化学领域的研究热点, 其在氨基酸的合成方面的应用也受到了极大的关注. 本综述第一次较为系统全面地总结了近些年有关电化学手段合成氨基酸的研究进展, 讨论了这些电化学方法在合成氨基酸类化合物方面的实际应用的可行性、具备的优势以及存在的一些局限, 为氨基酸绿色合成方面的研究提供了一定的参考.
王娜娜 , 徐敬成 , 梅海波 , Hiroki Moriwaki , Kunisuke Izawa , Vadim A. Soloshonok , 韩建林 . 电化学合成氨基酸类化合物的研究进展[J]. 有机化学, 2021 , 41(8) : 3034 -3049 . DOI: 10.6023/cjoc202102043
Due to the pivotal role of tailor-made amino acids in modern medicinal chemistry research and drug design, the interest in the development of synthetic methodology for preparation of these compounds is at an all-time high. Currently, electrochemical approaches for synthesis of amino acids are being actively pursued to take the advantage of sustainability and green chemistry facets offered by the electrochemistry. This work presents the first specially focused, comprehensive treatment of the literature data related to synthesis of amino acids via electrochemical means. Aspects of practicality, benefits and current shortcoming of this approach are critically discussed.
| [1] | For definition of Tailor-made amino acids, see: , Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045. |
| [2] | Tailor-Made Amino Acids™ is a trade-mark registered by Hamari Chemicals. |
| [3] | (a) Blaskovich, M. A. T. J. Med. Chem. 2016, 59, 10807. |
| [3] | (b) Mei, H.; Han, J.; Klika, K. D.; Izawa, K.; Sato, T.; Meanwell, N. A.; Soloshonok, V. A. Eur. J. Med. Chem. 2020, 186, 111826. |
| [3] | (c) Soloshonok, V. A.; Izawa, K. Asymmetric Synthesis and Application of α-Amino Acids, ACS Symposium Series #1009, Oxford University Press, 2009. |
| [3] | (d) Mei, H.; Han, J.; White, S.; Graham, D. J.; Izawa, K.; Sato, T.; Fustero, S.; Meanwell, N. A.; Soloshonok, V. A. Chem.-Eur. J. 2020, 26, 11349. |
| [3] | (e) Han, J.; Remete, A. M. Dobson, L. S.; Kiss, L.; Izawa, K.; Moriwaki, H.; Soloshonok, V. A.; O’Hagan, D. J. Fluorine Chem. 2020, 239, 109639. |
| [3] | (f) Yin, Z.; Hu, W.; Zhang, W.; Konno, H.; Moriwaki, H.; Izawa, K.; Han, J.; Soloshonok, V. A. Amino Acids 2020, 52, 1227. |
| [3] | (g) Liu, J.; Han, J.; Izawa, K.; Sato, T.; White, S.; Meanwell, N. A. Soloshonok, V. A. Eur. J. Med. Chem. 2020, 208, 112736. |
| [3] | (h) Mei, H.; Remete, A. M.; Zou, Y.; Moriwaki, H.; Fustero, S.; Kiss, L.; Soloshonok, V. A.; Han, J. Chin. Chem. Lett. 2020, 31, 2401. |
| [3] | (i) Mei, H.; Han, J.; Fustero, S.; Medio-Simon, M.; Sedgwick, D. M.; Santi, C.; Ruzziconi, R.; Soloshonok, V. A. Chem.-Eur. J. 2019, 25, 11797. |
| [4] | (a) Zhang, X. X.; Gao, Y.; Hu, X. S.; Ji, C. B.; Liu, Y. L.; Yu, J. S. Adv. Synth. Catal. 2020, 362, 4763. |
| [4] | (b) Ma, J. S. Chim. Oggi-Chem. Today 2003, 21, 65. |
| [4] | (c) Sato, T.; Izawa, K.; Acen?a, J. L.; Liu, H.; Soloshonok, V. A. Eur. J. Org. Chem. 2016, 2016, 2757. |
| [4] | (d) Larionov, V. A.; Stoletova, N. V.; Maleev, V. I. Adv. Synth. Catal. 2020, 362, 4325. |
| [4] | (e) Liu, J. Q.; Shatskiy, A.; Matsurra, B. S.; Kӓrkӓs, M. D. Synthesis 2019, 51, 2759. |
| [5] | (a) Hodgson, D. R. W.; Sanderson, J. M. Chem. Soc. Rev. 2004, 33, 422. |
| [5] | (b) Henninot, A.; Collins, J. C.; Nuss, J. M. J. Med. Chem. 2018, 61, 1382. |
| [5] | (c) Fosgerau, K.; Hoffmann, T. Drug Discovery Today 2015, 20, 122. |
| [5] | (d) Qiu, W.; Gu, X.; Soloshonok, V. A.; Carducci, M. D.; Hruby, V. J. Tetrahedron Lett. 2001, 42, 145. |
| [5] | (e) Craik, D. J.; Fairlie, D. P.; Liras, S.; Price, D. Chem. Biol. Drug Des. 2013, 81, 136. |
| [5] | (f) Stevenazzi, A.; Marchini, M.; Sandrone, G.; Vergani, B.; Lattanzio, M. Bioorg. Med. Chem. Lett. 2014, 24, 5349. |
| [6] | (a) Kim, Y.; Park, J.; Kim, M. J. ChemCatChem 2011, 3, 271. |
| [6] | (b) So, S. M.; Kim, H.; Mui, L.; Chin, J. Eur. J. Org. Chem. 2012, 2012, 229. |
| [6] | (c) D'Arrigo, P.; Cerioli, L.; Servi, S.; Viani, F.; Tessaroa, D. Cat. Sci. Technol. 2012, 2, 1606. |
| [6] | (d) Soloshonok, V. A.; Sorochinsky, A. E. Synthesis 2010, 2319. |
| [6] | (e) D'Arrigo, P.; Cerioli, L.; Fiorati, A.; Servi, S.; Viani, F.; Tessaroa, D. Tetrahedron: Asymmetry 2012, 23, 938. |
| [6] | (f) Bera, K.; Namboothiri, I. Asian J. Org. Chem. 2014, 3, 1234. |
| [6] | (g) Metz, A. E.; Kozlowski, M. C. J. Org. Chem. 2015, 80, 1. |
| [6] | (h) He, G.; Wang, B.; Nack, W. A.; Chen, G. Acc. Chem. Res. 2016, 49, 635. |
| [6] | (i) Han, J.; Sorochinsky, A. E.; Ono, T.; Soloshonok, V. A. Curr. Org. Synth. 2011, 8, 281. |
| [6] | (j) Sorochinsky, A. E.; Aceña, J. L.; Moriwaki, H.; Sato, T.; Soloshonok, V. A. Amino Acids 2013, 45, 691. |
| [6] | (k) Sorochinsky, A. E.; Aceña, J. L.; Moriwaki, H.; Sato, T.; Soloshonok, V. A. Amino Acids 2013, 45, 1017. |
| [6] | (l) Aceña, J. L.; Sorochinsky, A. E.; Soloshonok, V. Amino Acids 2014, 46, 2047. |
| [6] | (m) Aceña, J. L.; Sorochinsky, A. E.; Moriwaki, H.; Sato, T.; Soloshonok, V. A. J. Fluorine Chem. 2013, 155, 21. |
| [6] | (n) Qiu, X. L.; Qing, F. L. Eur. J. Org. Chem. 2011, 2011, 3261. |
| [6] | (o) Cao, H. Q.; Li, J. K.; Zhang, F. G.; Cahard, D.; Ma, J. A. Adv. Synth. Catal. 2021, 363, 688. |
| [7] | For selected reviews, see: a |
| [7] | (a) Yoshida, J.-I.; Kataoka, K.; Horcajada, R.; Nagaki, A. Chem. Rev. 2008, 108, 2265. |
| [7] | (b) Francke, R.; Little, R. D. Chem. Soc. Rev. 2014, 43, 2492. |
| [7] | (c) Sun, J.; Kong, W.; Jin, Z.; Han, Y.; Ma, L.; Ding, X.; Niu, Y.; Xu, Y. Chin. Chem. Lett. 2020, 31, 953. |
| [7] | (d) Jiang, Y.; Xu, K.; Zeng, C. Chem. Rev. 2018, 118, 4485. |
| [7] | (e) Waldvogel, S. R.; Lips, S.; Selt, M.; Riehl, B.; Kampf, C. J. Chem. Rev. 2018, 118, 6706. |
| [7] | (f) Mçhle, S.; Zirbes, M.; Rodrigo, E.; Gieshoff, T.; Wiebe, A.; Waldvogel, S. R. Angew. Chem., Int. Ed. 2018, 57, 6018. |
| [7] | (g) Moeller, K. D. Chem. Rev. 2018, 118, 4817. |
| [7] | (h) Wang, H.; Gao, X.; Lv, Z.; Abdelilah, T.; Lei, A. Chem. Rev. 2019, 119, 6769. |
| [7] | (i) Liu, J.; Lu, L.; Wood, D.; Lin, S. ACS Cent. Sci. 2020, 6, 1317. |
| [7] | (j) Beil, S. B.; Pollok, D.; Waldvogel, S. R. Angew. Chem., Int. Ed. 2021, 60,14750. |
| [7] | (k) Mei, H.; Yin, Z.; Liu, J.; Sun, H.; Han, J. Chin. J. Chem. 2019, 37, 292. |
| [7] | (k) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230. |
| [8] | (a) Chang, X.; Zhang, Q.; Guo, C. Angew. Chem., Int. Ed. 2020, 59, 12612. |
| [8] | (b) Mei, H. Pajkert, R.; Wang, L.; Li, Z.; Roeschenthaler, G. V.; Han, J. L. Green Chem. 2020, 22, 3028. |
| [9] | (a) Wang, Y.; Song, X.; Wang, J.; Moriwaki, H.; Soloshonok, V. A.; Liu, H. Amino Acids 2017, 49, 1487. |
| [9] | (b) Zou, Y.; Han, J.; Saghyan, A. S.; Mkrtchyan, A. F.; Konno, H.; Moriwaki, H.; Izawa, K.; Soloshonok, V. A. Molecules 2020, 25, 2739. |
| [9] | (c) Han, J.; Romoff, T. T.; Moriwaki, H.; Konno, H.; Soloshonok, V. A. ACS Omega 2019, 4, 18942. |
| [10] | (a) Zhou, S.; Wang, J.; Chen, X.; Aceña, J. L.; Soloshonok, V. A.; Liu, H. Angew. Chem., Int. Ed. 2014, 53, 7883. |
| [10] | (b) Zhou, S.; Wang, S.; Wang, J.; Nian, Y.; Peng, P.; Soloshonok, V. A.; Liu, H. Eur. J. Org. Chem. 2018, 2018, 1821. |
| [11] | (a) Romoff, T. T.; Palmer, A. B.; Mansour, N.; Creighton, C. J.; Miwa, T.; Ejima, Y.; Moriwaki, H.; Soloshonok, V. A. Org. Process Res. Dev. 2017, 21, 732. |
| [11] | (b) Romoff, T. T.; Ignacio, B. G.; Mansour, N.; Palmer, A. B.; Creighton, C. J.; Abe, H.; Moriwaki, H.; Han, J.; Konno, H.; Soloshonok, V. A. Org. Process Res. Dev. 2020, 24, 294. |
| [12] | (a) Wang, J.; Lin, D.; Zhou, S.; Soloshonok, V. A.; Liu, H. J. Org. Chem. 2011, 76, 684. |
| [12] | (b) Soloshonok, V. A.; Tang, X.; Hruby, V. J.; Meervelt, L. V. Org. Lett. 2001, 3, 341. |
| [12] | (c) Soloshonok, V. A.; Tang, X.; Hruby, V. J. Tetrahedron 2001, 57, 6375. |
| [13] | (a) Ellis, T. K.; Martin, C. H.; Tsai, G. M.; Ueki, H.; Soloshonok, V. A. J. Org. Chem. 2003, 68, 6208. |
| [13] | (b) Ellis, T. K.; Hochla, V. M.; Soloshonok, V. A. J. Org. Chem. 2003, 68, 4973. |
| [13] | (c) Ellis, T. K.; Martin, C. H.; Ueki, H.; Soloshonok, V. A. Tetrahedron Lett. 2003, 44, 1063. |
| [14] | (a) Wang, J.; Liu, H.; Aceña, J. L.; Houck, D.; Takeda, R.; Moriwaki, H.; Soloshonok, V. A. Org. Biomol. Chem. 2013, 11, 4508. |
| [14] | (b) Taylor, S. M.; Yamada, T.; Ueki, H.; Soloshonok, V. A. Tetrahedron Lett. 2004, 45, 9159. |
| [15] | (a) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547. |
| [15] | (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Tararov, V. I.; Saveleva, T. F.; Churkina, T. D.; Ikonnikov, N. S.; Kochetkov, K. A.; Orlova, S. A.; Pysarevsky, A. P.; Struchkov, Y. T.; Raevsky, N. I.; Belokon, Y. N. Tetrahedron: Asymmetry 1995, 6, 1741. |
| [16] | (a) Kawamura, A.; Moriwaki, H.; Röschenthaler, G.-V.; Kawada, K.; Aceña, J. L.; Soloshonok, V. A. J. Fluorine Chem. 2015, 171, 67. |
| [16] | (b) Soloshonok, V. A.; Avilov, D. V.; Kukhar, V. P.; Meervelt, L. V.; Mischenko, N. Tetrahedron Lett. 1997, 38, 4671. |
| [17] | (a) Yamada, T.; Okada, T.; Sakaguchi, K.; Ohfune, Y.; Ueki, H.; Soloshonok, V. A. Org. Lett. 2006, 8, 5625. |
| [17] | (b) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., nt. Ed. 2000, 39, 2172. |
| [17] | (c) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41, 9645. |
| [18] | (a) Yamada, T.; Sakaguchi, K.; Shinada, T.; Ohfune, Y.; Soloshonok, V. A. Tetrahedron: Asymmetry 2008, 19, 2789. |
| [18] | (b) Kawashima, A.; Shu, S.; Takeda, R.; Kawamura, A.; Sato, T.; Moriwaki, H.; Wang, J.; Izawa, K.; Aceña, J. L.; Soloshonok, V. A.; Liu, H. Amino Acids 2016, 48, 973. |
| [18] | (c) Kawashima, A.; Xie, C.; Mei, H.; Takeda, R.; Kawamura, A.; Sato, T.; Moriwaki, H.; Izawa, K.; Han, J.; Aceña, J. L.; Soloshonok, V. A. RSC Adv. 2015, 5, 1051. |
| [19] | Oyama, K.; Han, J.; Moriwaki, H.; Soloshonok, V. A.; Konno, H. Helv. Chim. Acta 2020, 103, e2000077. |
| [20] | Soloshonok, V. A.; Ellis, T. K.; Ueki, H.; Ono, T. J. Am. Chem. Soc. 2009, 131, 7208. |
| [21] | (a) Takeda, R.; Kawamura, A.; Kawashima, A.; Sato, T.; Moriwaki, H.; Izawa, K.; Akaji, K.; Wang, S.; Liu, H.; Aceña, J. L.; Soloshonok, V. A. Angew. Chem., Int. Ed. 2014, 53, 12214. |
| [21] | (b) Nian, Y.; Wang, J.; Zhou, S.; Wang, S.; Moriwaki, H.; Kawashima, A.; Soloshonok, V. A.; Liu, H. Angew. Chem., Int. Ed. 2015, 54, 12918. |
| [21] | (c) Sorochinsky, A. E.; Ueki, H.; Aceña, J. L.; Ellis, T. K.; Moriwaki, H.; Soloshonok, V. A. Org. Biomol. Chem. 2013, 11, 4503. |
| [22] | (a) Sorochinsky, A. E.; Ueki, H.; Aceña, J. L.; Ellis, T. K.; Moriwaki, H.; Sato, T.; Soloshonok, V. A. J. Fluorine Chem. 2013, 152, 114. |
| [22] | (b) Wang, S.; Zhou, S.; Wang, J.; Nian, Y.; Kawashima, A.; Moriwaki, H.; Aceña, J. L.; Soloshonok, V. A.; Liu, H. J. Org. Chem. 2015, 80, 9817. |
| [22] | (c) Nian, Y.; Wang, J.; Zhou, S.; Dai, W.; Wang, S.; Moriwaki, H.; Kawashima, A.; Soloshonok, V. A.; Liu, H. J. Org. Chem. 2016, 81, 3501. |
| [23] | Levitskiy, O. A.; Aglamazova, O. I.; Soloshonok, V. A.; Moriwaki, H.; Magdesieva, T. V. Eur. J. Org. Chem. 2020, 26, 7074. |
| [24] | Magdesieva, T. V.; Levitskiy, O. A.; Grishin, Y. K.; Ambartsumyan, A. A.; Kiskin, M. A.; Churakov, A. V.; Babievsky, K. K.; Kochetkov, K. A. Organometallics 2014, 33, 4629. |
| [25] | (a) Soloshonok, V. A.; Ueki, H. J. Am. Chem. Soc. 2007, 129, 2426. |
| [25] | (b) Soloshonok, V. A.; Ono, T.; Ueki, H.; Vanthuyne, N.; Balaban, T. S.; Bürck, J.; Fliegl, H.; Klopper, W.; Naubron, J. V.; Tam, T. T.; Drake, A. F.; Roussel, C. J. Am. Chem. Soc. 2010, 132, 10477. |
| [26] | Magdesieva, T. V.; Levitskiy, Oleg A.; Grishin, Y. K.; Ambartsumyan, A. A.; Paseshnichenko, K. A.; Kolotyrkina, N. G.; Kochetkov, K. A. Organometallics 2014, 33, 4639. |
| [27] | Levitskiy, O. A.; Grishin, Y. K.; Semivrazhskaya, O. O.; Ambartsumyan, A. A.; Kochetkov, K. A.; Magdesieva, T. V. Angew. Chem., Int. Ed. 2017, 56, 2704. |
| [28] | Frian, A. W.; Sherif, S. M. Tetrahedron 1999, 55, 7957. |
| [29] | Castanheiro, T.; Suffert, J.; Donnard, M.; Gulea, M. Chem. Soc. Rev. 2016, 45, 494. |
| [30] | Levitskiy, O. A.; Grishin, Y. K.; Paseshnichenko, K. A.; Kochetkov, K. A. Magdesieva, T. V. Tetrahedron Lett. 2018, 59, 2831. |
| [31] | Levitskiy, O. A.; Grishin, Y. K.; Magdesieva, T. V. Eur. J. Org. Chem. 2019, 2019, 3174. |
| [32] | Levitskiy, O. A.; Aglamazova, O. I.; Magdesieva, T. V. Electrochim. Acta 2019, 306, 568. |
| [33] | Levitskiy, O. A.; Aglamazova, O. I.; Grishin, Y. K.; Paseshnichenko, K. A.; Magdesieva, T. V. ChemElectroChem 2020, 7, 3361. |
| [34] | Nelson, D. L.; Cox, M. M. Lehninger, Principles of Biochemistry, 3rd ed, Worth Publishing, New York, 2000. |
| [35] | (a) Han, J.; Sorochinsky, A. E.; Ono, T.; Soloshonok, V. A. Curr. Org. Synth. 2011, 8, 281. |
| [35] | (b) Soloshonok, V. A.; Kirilenko, A. G.; Kukhar, V. P.; Resnati, G. Tetrahedron Lett. 1993, 34, 3621. |
| [36] | (a) Soloshonok, V. A.; Kukhar, V. P. Tetrahedron 1996, 52, 6953. |
| [36] | (b) Soloshonok, V. A.; Kukhar, V. P. Tetrahedron 1997, 53, 8307. |
| [37] | (a) Jeffery, E. A.; Meisters, A. Aust. J. Chem. 1978, 31, 73. |
| [37] | (b) Jeffery, E. A.; Johansen, O.; Meisters, A. Aust. J. Chem. 1978, 31, 79. |
| [37] | (c) Jubault, M.; Raoult, E. J. Chem. Soc., hem. Commun. 1977, 250. |
| [38] | (a) Degani, Y.; Heller, A. J. Am. Chem. Soc. 1989, 111, 2357. |
| [38] | (b) Kuwabata, S.; Okamoto, T.; Kajiya, Y.; Yoneyama, H. Anal. Chem. 1995, 34, 1684. |
| [38] | (c) Yuan, R.; Watanabe, S.; Kuwabata, S.; Yoneyama, H. J. Org. Chem. 1997, 62, 2494. |
| [39] | Kawabata, S.; Iwata, N.; Yoneyama, H. Chem. Lett. 2000, 29, 110. |
| [40] | (a) Sorochinsky, A. E.; Katagiri, T.; Ono, T.; Wzorek, A.; Aceña, J. L.; Soloshonok, V. A. Chirality 2013, 25, 365. |
| [40] | (b) Sorochinsky, A. E.; Aceña, J. L.; Soloshonok, V. A. Synthesis 2013, 45, 141. |
| [40] | (c) Han, J.; Nelson, D. J.; Sorochinsky, A. E.; Soloshonok, V. A. Curr. Org. Synth. 2011, 8, 310. |
| [41] | (a) Han, J. L.; Kitagawa, O.; Wzorek, A.; Klika, K. D.; Soloshonok, V. A. Chem. Sci. 2018, 9, 1718. |
| [41] | (b) Soloshonok, V. A.; Wzorek, A.; Klika, K. D. Tetrahedron: Asymmetry 2017, 28, 1430. |
| [42] | (a) Takashi, F.; Miho, Y. Chem. Commun. 2019, 55, 14721. |
| [42] | (b) Becker, J.; Wittmann, C. Curr. Opin. Biotechnol. 2012, 23, 718. |
| [42] | (c) D'Este, M.; Alvarado-Morales, M.; Angelidaki, I. Biotechnol. Adv. 2018, 36, 14. |
| [43] | Fukushima, T.; Yamauchi, M. J. Appl. Electrochem. 2020, 51, 99. |
| [44] | Wu, R.; Ma, C.; Zhu, Z. Curr. Opin. Electrochem. 2020, 19, 1. |
| [45] | Wu, R.; Zhu, Z. ACS Sustainable Chem. Eng. 2018, 6, 12593. |
| [46] | (a) Xiao, X.; Xia, H.; Wu, R.; Bai, L.; Yan, L.; Magner, E.; Cosnier, S.; Lojou, E.; Zhu, Z.; Liu, A. Chem. Rev. 2019, 119, 9509. |
| [46] | (b) Mazurenko, I.; Etienne, M.; Kohring, G.-W.; Lapicque, F.; Walcarius, A. Electrochim. Acta 2016, 199, 342. |
| [47] | Chen, H.; Prater, M.; Cai, R.; Dong, F.; Chen, H.; Minteer, S. J. Am. Chem. Soc. 2020, 142, 4028. |
| [48] | Cook, R. L.; Sommells, A. F. J. Electrochem. Soc. 1989, 136, 1845. |
| [49] | Hughes, D. L.; Ibrahim, S. K.; Macdonald, C. J.; Ali, H. M.; Pickett, C. J. J. Chem. Soc.,Chem. Commun. 1992, 1762. |
| [50] | Strecker, A. Ann. Chem. Pharm. 1850, 75, 27. |
| [51] | (a) Silvestri, G.; Gambino, S.; Filardo, G. Acta Chem. Scand. 1991, 45, 987. |
| [51] | (b) Nitopi, S.; Bertheussen, E.; Scott, S. B.; Liu, X.; Engstfeld, A. K.; Horch, S.; Seger, B.; Stephens, I. E. L.; Chan, K.; Hahn, C.; Nørskov, J. K.; Jaramillo, T. F.; Chorkendorff, I. Chem. Rev. 2019, 119, 7610. |
| [51] | (c) Lv, J.-J.; Jouny, M.; Luc, W.; Zhu, W.; Zhu, J.-J.; Jiao, F. Adv. Mater. 2018, 30, 1803111. |
| [51] | (d) Zhu, W.; Kattel, S.; Jiao, F.; Chen, J. G. Adv. Energy Mater. 2019, 9, 1802840. |
| [51] | (e) Zhang, K.; Wang, H.; Zhao, S.-F.; Niu, D.-F.; Lu, J.-X. J. Electroanal. Chem. 2009, 630, 35. |
| [51] | (f) Zhao, S.-F.; Zhu, M.-X.; Zhang, K.; Wang, H.; Lu, J.-X. Tetrahedron Lett. 2011, 52, 2702. |
| [51] | (g) Chen, B.-L.; Tu, Z.-Y.; Zhu, H.-W.; Sun, W.-W.; Wang, H.; Lu, J.-X. Electrochim. Acta 2014, 116, 475. |
| [51] | (h) Chen, B.-L.; Zhu, H.-W.; Xiao, Y.; Sun, Q.-L.; Wang, H.; Lu, J.-X. Electrochem. Commun. 2014, 42, 55. |
| [51] | (i) Jiao, K.-J.; Li, Z.-M.; Xu, X.-T.; Zhang, L.-P.; Li, Y.-Q.; Zhang, K.; Mei, T.-S. Org. Chem. Front. 2018, 5, 2244. |
| [52] | (a) Bringmann, J.; Dinjus, E. Appl. Organomet. Chem. 2001, 15, 135. |
| [52] | (b) Wang, H.; Zhang, G. R.; Liu, Y. Z.; Luo, Y. W.; Lu, J. X. Electrochem. Commun. 2007, 9, 2235. |
| [52] | (c) Dérien, S.; Duñach, E.; Périchon, J. J. Am. Chem. Soc. 1991, 113, 8447. |
| [52] | (d) Koster, F.; Dinjus, E.; Duñach, E. Eur. J. Org. Chem. 2001, 2507. |
| [53] | (a) Chan, A. S. C.; Huang, T. T.; Wagenknecht, J. H.; Miller, R. E. J. Org. Chem. 1995, 60, 742. |
| [53] | (b) Scialdone, O.; Sabatino, M. A.; Belfiore, C.; Galia, A.; Paternostro, M. P.; Filardo, G. Electrochim. Acta 2006, 51, 3500. |
| [53] | (c) Scialdone, O.; Galia, A.; Isse, A. A.; Gennaro, A.; Sabatino, M. A.; Leone, R.; Filardo, G. J. Electroanal. Chem. 2007, 609, 8. |
| [54] | (a) Zheng, G. D.; Stradiotto, M.; Li, L. J. J. Electroanal. Chem. 1998, 453, 79. |
| [54] | (b) Amatore, C.; Jutand, A. J. Am. Chem. Soc. 1991, 113, 2819. |
| [54] | (c) Isse, A. A.; Gennaro, A. Chem. Commun. 2002, 2798. |
| [54] | (d) Scialdone, O.; Galia, A.; Errante, G.; Isse, A. A.; Gennaro, A.; Filardo, G. Electrochim. Acta 2008, 53, 2514. |
| [54] | (e) Anandhakumar, S.; Sripriya, R.; Chandrasekaran, M.; Govindu, S.; Noel, M. J. Appl. Electrochem. 2009, 39, 463. |
| [55] | (a) Gennaro, A.; Sanchez-Sanchez, C. M.; Isse, A. A.; Montiel, V. Electrochem. Commun. 2004, 6, 627. |
| [55] | (b) Feroci, M.; Orsini, M.; Rossi, L.; Sotgiu, G.; Inesi, A. J. Org. Chem. 2007, 72, 200. |
| [55] | (c) Yang, H. Z.; Gu, Y. L.; Deng, Y. Q.; Shi, F. Chem. Commun. 2002, 274. |
| [56] | (a) Titov, V. E.; Bondarenko, V. N.; Koshechko, V. G.; Pokhodenko, V. D. Theor. Chem. Acc. 2008, 44, 271. |
| [56] | (b) Koshechko, V. G.; Titov, V. E.; Bondarenko, V. N.; Pokhodenko, V. D. J. Fluorine Chem. 2008, 129, 701. |
| [57] | Li, C. H.; Song, X. Z.; Tao, L. M.; Li, Q. G.; Xie, J. Q.; Peng, M. N.; Pan, L.; Jiang, C.; Peng, Z. Y.; Xu, M. F. Tetrahedron 2014, 70, 1855. |
| [58] | Qu, Y.; Tsuneishi, C.; Tateno, H.; Matsumura, Y.; Atobe, M. React. Chem. Eng. 2017, 2, 871. |
| [59] | Gennaro, A.; Sánchez-Sánchez, C. M.; Isse, A. A.; Montiel, V. Electrochem. Commun. 2004, 6, 627. |
| [60] | Izawa, K.; Nishi, S.; Asada, S. J. Mol. Catal. 1987, 41, 135. |
| [61] | Shono, T.; Matsumura, Y.; Tsubata, K. Org. Synth. 1984, 63, 206. |
| [62] | Amino, Y.; Nishi, S.; Izawa, K. Chem. Pharm. Bull. 2017, 65, 854. |
| [63] | Olsen, R. K.; Kolar, A. J. Tetrahedron Lett. 1975, 16, 3579. |
| [64] | Iwasa, T.; Horikawa, H.; Matsumoto, K.; Miyoshi, M. J. Org. Chem. 1977, 42, 2419. |
| [65] | Iwaski, T.; Horikawa, H.; Matsumoto, K.; Mioshi, M. B. Chem. Soc. Jpn. 1979, 52, 826. |
| [66] | (a) Roberts, J. L.; Chan, C. Tetrahedron Lett. 2002, 43, 7679. |
| [66] | (b) Paradisi, F.; Porzi, G.; Rinaldi, S.; Sandri, S. Tetrahedron: Asymmetry 2000, 11, 1259. |
| [67] | Sutherland, A.; Vederas, J. C. Chem. Commun. 2002, 224. |
| [68] | (a) Soloshonok, V. A.; Sorochinsky, A. E. Synthesis 2010, 2319. |
| [68] | (b) Taylor, S. M.; Yamada, T.; Ueki, H.; Soloshonok, V. A. Tetrahedron Lett. 2004, 45, 9159. |
| [68] | (c) Wang, J.; Liu, H.; Aceña, J. L.; Houck, D.; Takeda, R.; Moriwaki, H.; Sato, T.; Soloshonok, V. A. Org. Biomol. Chem. 2013, 11, 4508. |
| [69] | Hiebl, J.; Blanka, M.; Guttman, A.; Kollmann, H.; Leitner, K.; Mayrhofer, G.; Rovenszky, F.; Winkler, K. Tetrahedron 1998, 54, 2059. |
| [70] | Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 2003, 44, 2137. |
| [71] | Konare, A. A.; Lukyanets, E. A.; Negrimovskii, V. M. Russ. J. Electrochem. 2007, 43, 1252. |
| [72] | Matsumura, Y.; Kinoshita, T.; Yanagihara, Y.; Kanemoto, N.; Watanabe, M. Tetrahedron Lett. 1996, 37, 8395. |
| [73] | Kirira, P. G.; Kuriyama, M.; Onomura, O. Chem.-Eur. J. 2010, 16, 3970. |
| [74] | Orata, D.; Segor, F. Catal. Lett. 1999, 58, 157. |
| [75] | Duquenne, C.; Goumain, S.; Jubault, P.; Feasson, C.; Quirion, J. C. Org. Lett. 2000, 2, 453. |
| [76] | Asada, S.; Kato, M.; Asai, K.; lneyama, T.; Nishi, S.; Izawa, K.; Shono, T. J. Chem. Soc., Chem. Commun. 1989, 486. |
| [77] | Kang, L. S.; Luo, M. H.; Lam, C. M.; Hu, L. M.; Little, R. D.; Zeng, C. C. Green Chem. 2016, 18, 3767. |
| [78] | (a) Han, J.; Wzorek, A.; Kwiatkowska, M.; Soloshonok, V. A.; Klika, K. D. Amino Acids 2019, 51, 865. |
| [78] | (b) Hosaka, T.; Imai, T.; Wzorek, A.; Marcinkowska, M.; Kolbus, A.; Kitagawa, O.; Soloshonok, V. A.; Klika, K. D. Amino Acids, 2019, 51, 283. |
| [78] | (c) Han, J.; Soloshonok, V. A.; Klika, K. D.; Drabowicz, J.; Wzorek, A. Chem. Soc. Rev. 2018, 47, 1307. |
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