Chinese Journal of Organic Chemistry >
Research Progress of Photoelectric Co-catalysis
Received date: 2021-06-26
Revised date: 2021-08-20
Online published: 2021-09-03
Supported by
Youth Project of Natural Science Foundation of Heilongjiang Province(YQ2019B004)
Photochemical and electrochemical reactions, which are mild and green, have been widely used in organic synthesis in recent years. To push the limits of both synthetic technologies, organic chemists have focused on using these two strategies to promote organic transformation in a single reaction system. A series of photoelectrochemical strategies have been developed, and the main one at present is electrochemically mediated photoredox catalysis. In addition, photoexcitation-assisted electroredox strategies have also gradually shown their potential in organic synthesis. These strategies realize the complementary advantages and disadvantages of photochemistry and electrochemistry, and can solve the problems that can not be solved by a single synthetic technology, such as removing oxidizing reducing agents that complicate the reaction, generating intermediates with high activity under mild conditions, and so on. In this paper, the research progress of photoelectrochemical strategies is summarized according to the existing photoelectric catalysis reactions, and the possible mechanism of some reactions is discussed.
Key words： photoredox catalysis; electrocatalysis; photoelectrochemistry
Yingjie Liu , Zhichuan Wang , Jianping Meng , Chen Li , Kai Sun . Research Progress of Photoelectric Co-catalysis[J]. Chinese Journal of Organic Chemistry, 2022 , 42(1) : 100 -110 . DOI: 10.6023/cjoc202106051
| [1] | Faraday, M. Ann. Phys. (Leipzig) 1834, 47, 438. |
| [2] | Kolbe, H. J. Prakt. Chem. 1847, 41, 137. |
| [3] | Schoenbein, Ch. F. Liebigs Ann. Chem. 1845, 54, 164. |
| [4] | Liu, Y.-J.; Han, Y.-H.; Lin, L.-Q.; Xu, Y. Chin. J. Org. Chem. 2021, 41, 934. (in Chinese) |
| [4] | (刘颖杰, 韩莹徽, 林立青, 许颖, 有机化学, 2021, 41, 934.) |
| [5] | Sun, K.; Lei, J.; Liu, Y.-J.; Liu, B.; Chen, N. Adv. Synth. Catal. 2020, 362, 3709. |
| [6] | Yuan, Y.; Lei, A.-W. Acc. Chem. Res. 2019, 52, 3309. |
| [7] | Ischay, M. A.; Anzovino, M. E.; Du, J.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 12886. |
| [8] | Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77. |
| [9] | Narayanam, M. R.; Tucker, J. W.; Stephenson, C. R. J. J. Am. Chem. Soc. 2009, 131, 8756. |
| [10] | Gan, Z.-Y.; Li, G.-Q.; Yang, X.-B.; Yan, Q.-L.; Xu, G.-Y.; Li, G.-Y.; Jiang, Y.-Y.; Yang, D.-S. Sci. China: Chem. 2020, 63, 1652. |
| [11] | Xie, J.; Jin, H.; Hashmi, A. S. K. Chem. Soc. Rev. 2017, 46, 5193. |
| [12] | Becker, M. R.; Richardson, A. D.; Schindler, C. S. Nat. Commun. 2019, 10, 5095. |
| [13] | Kong, Y.-L.; Xu, W.-X.; Ye, F.-X.; Weng, J.-Q. Chin. J. Org. Chem. 2019, 39, 3065. (in Chinese) |
| [13] | (孔瑶蕾, 徐雯秀, 叶飞霞, 翁建全, 有机化学, 2019, 39, 3065.) |
| [14] | Moutet, J. C.; Reverdy, G. Tetrahedron Lett. 1979, 20, 2389. |
| [15] | Moutet, J. C.; Reverdy, G. J. Chem. Soc.,Chem. Commun. 1982, 654. |
| [16] | Yu, Y.; Guo, P.; Zhong, J.-S.; Yuan, Y.; Ye, K.-Y. Org. Chem. Front. 2020, 7, 131. |
| [17] | Capaldo, L.; Quadri, L. L.; Ravelli, D. Angew. Chem.,Int. Ed. 2019, 58, 17508. |
| [18] | Barham, J. P.; König, B. Angew. Chem.,Int. Ed. 2020, 59, 11732. |
| [19] | Chen, N.; Xu, H.-C. Chem. Rec. 2021, 21, 1. |
| [20] | Qiu, Y.; Scheremetjew, A.; Finger, L. H.; Ackermann, L. Chem.- Eur. J. 2020, 26, 3241. |
| [21] | Ouyang, Y.; Xu, X.-H.; Qing, F.-L. Angew. Chem.,Int. Ed. 2018, 57, 6926. |
| [22] | Deng, Y.; Lu, F.-L.; You, S.-Q.; Xia, T.-R.; Zheng, Y.-F.; Lu, C.-F.; Yang, G.-C.; Chen, Z.-X.; Gao, M.; Lei, A.-W. Chin. J. Chem. 2019, 37, 817. |
| [23] | Yan, H.; Hou, Z.-W.; Xu, H.-C. Angew. Chem., nt. Ed. 2019, 58, 4592. |
| [24] | Lai, X.-L.; Shu, X.-M.; Song, J.; Xu, H.-C. Angew. Chem.,Int. Ed. 2020, 59, 10626. |
| [25] | Koeller, J.; Gandeepan, P.; Ackermann, L. Synthesis 2019, 51, 1284. |
| [26] | Tian, W.-F.; Hu, C.-H.; He, K.-H.; He, X.-Y.; Li, Y. Org. Lett. 2019, 21, 6930. |
| [27] | Kurihara, H.; Fuchigami, T.; Tajima, T. J. Org. Chem. 2008, 73, 6888. |
| [28] | Xiang, J.; Shang, M.; Kawamata, Y.; Lundberg, H.; Reisberg, S. H.; Chen, M.; Mykhailiuk, P.; Beutner, G.; Collins, M. R.; Davies, A.; Del Bel, M.; Gallego, G. M.; Spangler, J. E.; Starr, J.; Yang, S.; Blackmond, D. G.; Baran, P. S. Nature 2019, 573, 398. |
| [29] | Xu, F.; Lai, X.-L.; Xu, H.-C. Synlett 2021, 32, 369. |
| [30] | Niu, L.; Jiang, C.-Y.; Liang, Y.-W.; Liu, D.-D.; Bu, F.-X.; Shi, R.-Y.; Chen, H.; Chowdhury, A. D.; Lei, A.-W. J. Am. Chem. Soc. 2020, 41, 17693. |
| [31] | Yang, Y. Z.; Song, R. J.; Li, J. H. Org. Lett. 2019, 21, 3228. |
| [32] | Zhang, W.; Carpenter, K. L.; Lin, S. Angew. Chem., Int. Ed. 2020, 59, 409. |
| [33] | Zelenka, J.; Svobodová, E.; Tarábek, J.; Hoskovcová, I.; Boguschová, V.; Bailly, S.; Sikorski, M.; Roithová, J.; Cibulka, R. Org. Lett. 2019, 21, 114. |
| [34] | Capaldo, L.; Quadri, L. L.; Merli, D.; Ravelli, D. Chem. Commun. 2021, 57, 4424. |
| [35] | Hou, Z.-W.; Xu, H.-C. ChemElectroChem 2021, 8, 1571. |
| [36] | Huang, H.; Strater, Z. M.; Rauch, M.; Shee, J.; Sisto, T. J.; Nuckolls, C.; Lambert, T. H. Angew. Chem.,Int. Ed. 2019, 58, 13318. |
| [37] | Huang, H.; Lambert, T. H. Angew. Chem.,Int. Ed. 2020, 59, 658. |
| [38] | Huang, H.; Strater, Z. M.; Lambert, T. H. J. Am. Chem. Soc. 2020, 142, 1698. |
| [39] | Tao, S.; Lambert, T. H. Science 2021, 371, 620. |
| [40] | Kim, H.; Kim, H.; Lambert, T. H.; Lin, S. J. Am. Chem. Soc. 2020, 142, 2087. |
| [41] | Cowper, N. G. W.; Chernowsky, C. P.; Williams, O. P.; Wickens, Z. K. J. Am. Chem. Soc. 2020, 142, 2093. |
| [42] | Chen, J.; Yan, W.-Q.; Lam, C. M.; Zeng, C. C.; Hu, L.-M.; Little, R. D. Org. Lett. 2015, 17, 986. |
| [43] | Kiyokawa, K.; Kosaka, T.; Minakata, S. Org. Lett. 2013, 15, 4858. |
| [44] | Wang, F.; Stahl, S. S. Angew. Chem.,Int. Ed. 2019, 58, 6385. |
| [45] | Herold, S.; Bafaluy, D.; Muñiz, K. Green Chem. 2018, 20, 3191. |
| [46] | Hu, X.; Zhang, G.-T.; Bu, F.-X.; Nie, L.; Lei, A.-W. ACS Catal. 2018, 8, 9370. |
| [47] | Shono, T.; Matsumura, Y.; Katoh, S.; Takeuchi, K.; Sasaki, K.; Kamada, T.; Shimizu, R. J. Am. Chem. Soc. 1990, 112, 2368. |
| [48] | Zhang, S.; Li, L.; Xue, M.; Zhang, R.; Xu, K.; Zeng, C. Org. Lett. 2018, 20, 3443. |
| [49] | Liu, Y.; Lin, L.-Q.; Han, Y.-H.; Liu, Y.-J. Chin. J. Org. Chem. 2020, 40, 4216. (in Chinese) |
| [49] | (刘洋, 林立青, 韩莹徽, 刘颖杰, 有机化学, 2020, 40, 4216.) |
| [50] | Xu, P.; Chen, P.-Y.; Xu, H.-C. Angew. Chem.,Int. Ed. 2020, 59, 14275. |
/
| 〈 |
|
〉 |
