Chinese Journal of Organic Chemistry >
Progress of α-Position Functionalization of Ethers under Photo/Electrocatalysis
Received date: 2023-05-10
Revised date: 2023-06-25
Online published: 2023-07-27
Supported by
The Natural Science Foundation of Heilongjiang Province(LH2020H068); The Innovative Talent Project of Ministry of Education of Heilongjiang Province(UNPYSCT-2018139); The Construction and Cultivation of Collaborative Innovation Achievements of Disciplines in Colleges and Universities(LJGXCG2022-086)
Ethers are widely used in organic chemistry, materials science, biomedicine and other fields due to their excellent physicochemical properties. Among them, tetrahydrofuran/tetrahydrothiophene and their derivatives are the core backbones for building biologically active molecules and complex natural products. In recent years, photo/electrocatalysis has gradually become an important tool for chemists to synthesize novel compounds due to its compliance with the requirements of green chemistry and the unique pathway that mostly involves radical intermediates. The functionalization of α-positions of ethers using photo/electrocatalysis is a green and efficient synthetic strategy. Therefore, the research progress of photo/electro- catalytic functionalization of ether compounds at the α-position is reviewed with ether/sulfide as examples, and a detailed description of some of the mechanisms is provided.
Yingjie Liu , Gangqing Shi , Ge Chou , Xin Zhang , Dongxue Song , Ning Chen , Miao Yu , Ying Xu . Progress of α-Position Functionalization of Ethers under Photo/Electrocatalysis[J]. Chinese Journal of Organic Chemistry, 2023 , 43(8) : 2664 -2681 . DOI: 10.6023/cjoc202305011
| [1] | Dong, G.-B.; Liu, P.; Yu, X.; Kevlishvili, l.; Lyu, H. Science 2021, 372, 175. |
| [2] | Qin, Y.; Zhu, L.-H.; Luo, S.-Z. Chem. Rev. 2017, 117, 9433. |
| [3] | Wang, Z.-C.; Li, Zhen.-J.; Sun, K. Chin. Chem. Lett. 2023, 34, 108045. |
| [4] | Saleem, M.; Kim, H. J.; Ali, M. S.; Lee, Y. S. Nat. Prod. Rep. 2005, 22, 696. |
| [5] | Faul, M. M.; Huff, B. E. Chem. Rev. 2000, 100, 2407. |
| [6] | Jeffrey, J. L.; Terrett, J. A.; MacMillan, D. W. C. Science 2015, 349, 1532. |
| [7] | Esswein, A. J.; Nocera, D. G. Chem. Rev. 2007, 107, 4022. |
| [8] | Wan, M.; Meng, Z.-L.; Lou, H.-X.; Liu, L. Angew. Chem. Int. Ed. 2014, 53, 13845. |
| [9] | Wang, G.; Xin, X.-D. Wang, Z.-H.; Lu, G.; Ma, Y.-D.; Liu, L. Nat. Commun. 2019, 10, 559. |
| [10] | Morton, C. M.; Zhu, Q.-L.; Ripberger, H.; Troian-Gautier, L.; Toa, Z. S. D.; Knowles, R. R.; Alexanian, E. J. J. Am. Chem. Soc. 2019, 141, 13253. |
| [11] | Mammoli, V.; Bonifazi, A.; Del Bello, F.; Diamanti, E.; Giannella, M.; Hudson, A. L.; Mattioli, L.; Perfumi, M.; Piergentili, A.; Quaglia, W.; Titomanlio, F.; Pigini, M. Bioorg. Med. Chem. 2012, 20, 2259. |
| [12] | (a) Wencel-Delord, J.; Glorius, F. Nat. Chem. 2013, 5, 369. |
| [12] | (b) Paolillo, J. M.; Duke, A. D.; Gogarnoiu, E. S.; Wise, D. E.; Parasram, M. J. Am. Chem. Soc. 2023, 145, 2794. |
| [13] | Noisier, A. F. M.; Brimble, M. A. Chem. Rev. 2014, 114, 8775. |
| [14] | Wang, X.-Y, Luo, N.-C, Wang, F. Chin. J. Chem. 2022, 40, 1492. |
| [15] | Guo, X.-X.; Gu, D.-W.; Wu, Z.-X.; Zhang, W.-B. Chem. Rev. 2015, 115, 1622. |
| [16] | Du, W.; Gu, Q.-S.; Li, Z.-L.; Yang, D. J. Am. Chem. Soc. 2015, 137, 1130. |
| [17] | Song, R.-J.; Tu, Y.-Q.; Zhu, D.-Y.; Zhang, F.-M.; Wang, S.-H. Chem. Commun. 2015, 51, 749. |
| [18] | Yang, Y.; Cho, I.; Qi, X.-T.; Liu, P.; Arnold, F. H. Nat. Chem. 2019, 11, 987. |
| [19] | Cui, H.-B.; Xie, L.-Z.; Wan, N.-W.; He, Q.; Li, Z.; Chen, Y.-Z. Green Chem. 2019, 21, 4324. |
| [20] | Alwaseem, H.; Giovani, S.; Crotti, M.; Welle, K.; Jordan, C. T.; Ghaemmagham, S.; Fasan, R. ACS Cent. Sci. 2021, 7, 841. |
| [21] | Wang, X.; Meng, J.-P.; Zhao, D.-Y.; Tang, S.; Sun, K. Chin. Chem. Lett. 2023, 34, 107736. |
| [22] | Deshidi, R.; Rizvi, M. A.; Shah, B. A. RSC Adv. 2015, 5, 90521. |
| [23] | Qin, W.-J.; Li, Y.; Yu, X.-X.; Deng, W.-P. Tetrahedron 2015, 71, 1182. |
| [24] | (a) Sun, K.; Zhao, D.-Y.; Li, Q.-X.; Ni, S.-F.; Zheng, G.-F.; Zhang, Q. Sci. China Chem. 2023, doi:10.1007/s11426-023-1622-1. |
| [24] | (b) Gao, C.; Xiong, Y.-J. Chin. J. Chem. 2022, 40, 153. |
| [25] | Kalthoff, F. S.; James, M. J.; Teders, M.; Pitzer, L.; Glorius, F. Chem. Soc. Rev. 2018, 47, 7190. |
| [26] | Qin, Q.; Jiang, H.; Hu, Z.-T.; Ren, D.-A.; Yu, S.-Y. Chem. Rec. 2017, 17, 754. |
| [27] | Ravelli, D.; Protti, S.; Fagnoni, M. Acc. Chem. Res. 2016, 49, 2232. |
| [28] | Sperry, J. B. Wright, D. L. Chem. Soc. Rev. 2006, 35, 605. |
| [29] | Takacs, J. M.; Jiang, X.-T. Curr. Org. Chem. 2003, 7, 369. |
| [30] | Guo, S.-R.; Kumar, P. S.; Yang, M.-H. Adv. Synth. Catal. 2017, 359, 2. |
| [31] | Sun, K.; Lei, J.; Liu, Y.-J.; Liu, B.; Chen, N. Adv. Synth. Catal. 2020, 362, 3709. |
| [32] | (a) Yu, W.-J.; Wang, S.-C.; He, M.; Jiang, Z.; Yu, Y.; Lan, J.-P.; Luo, J.; Wang, P.-J.; Qi, X.-T.; Wang, T.; Lei, A.-W. Angew. Chem. Int. Ed. 2023, 135, e202219166. |
| [32] | (b) Chen, M.-X, Liu, Y.; Song, T.-W.; Wei, R.-L.; Zhuang, X.-D.; Yang, Y.-Y.; Liang, H.-W. Chin. J. Chem. 2022, 40, 2161. |
| [33] | Yan, H.; Hou, Z.-W.; Xu, H.-C. Angew. Chem. Int. Ed. 2019, 58, 4592. |
| [34] | Lai, X.-L.; Shu, X.-M.; Song, J.; Xu, H.-C. Angew. Chem. Int. Ed. 2020, 59, 10626. |
| [35] | Koeller, J.; Gandeepan, P.; Ackermann, L. Synthesis 2019, 51, 1284. |
| [36] | Fan, X.-Z.; Rong, J.-W.; Wu, H.-L.; Zhou, Q.; Deng, H.-P.; Tan, J.-D.; Xue, C.-W.; Wu, L.-Z.; Tao, H.-R.; Wu, J. Angew. Chem. Int. Ed. 2018, 57. 8514. |
| [37] | Qiao, J.; Song, Z.-Q.; Huang, C.; Ci, R, -N.; Liu, Z.; Chen, B.; Tung, C.-G.; W, L.-Z. Angew. Chem. Int. Ed. 2021, 60, 27201. |
| [38] | Pulcinella, A.; Bonciolini, S.; Lukas, F.; Sorato, A.; No?l, T. Angew. Chem. Int. Ed. 2023, 135, e202215374. |
| [39] | Liu, Z.-H.; Wang, H.-W.; Sivaguru, P.; Nolan, S. P.; Song, Q.-M.; Yu, W.-J.; Jiang, X.-J.; Anderson, E. A.; Bi, X.-H. Nat. Commun. 2022, 13, 1674. |
| [40] | Feng, S.-B.; Xie, X.-G.; Zang, W.-W.; Liu, L.; Zhong., Z.-Z.; Xu, D.-Y.; She, X.-G. Org. Lett. 2016, 18, 3846. |
| [41] | Heitz, D. R.; Tellis., J. C.; Molander, G. A. J. Am. Chem. Soc. 2016, 138, 12715. |
| [42] | Kamijo. S.; Takao. G.; Kamijo. K.; Hirota. M.; Tao. K.; Murafuji. T. Angew. Chem. Int. Ed. 2016, 55, 9695. |
| [43] | Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. |
| [44] | Deng, H.-P.; Fan, X.-Z.; Chen, Z.-H.; Xu, Q.-H.; Wu, J. J. Am. Chem. Soc. 2016, 139, 13579. |
| [45] | Zhang, M.; Zhao, Y.; Chen, W.-Z. Synthesis 2017, 49, 1342 |
| [46] | Go, S. Y.; Lee, G. S.; Hong, S. H. Org. Lett. 2018, 20, 4691. |
| [47] | Song, Z.-Q.; Liu, Z.; Gan, Q.-C.; Lei, T.; Tung, C.-H.; Wu, L.-Z. Org. Lett. 2020, 22, 832. |
| [48] | Singsardar, M.; Laru, S.; Mondal, S.; Hajra, A. J. Am. Chem. Soc. 2019, 84, 4543. |
| [49] | Kibriya, G.; Bagdi, A. K.; Hajra, A. J. Org. Chem. 2018, 83, 10619. |
| [50] | Wan, Z.-J.; Yuan, X.-F.; Luo, J. Org. Biomol. Chem. 2020, 18, 3258. |
| [51] | Jiang, S.; Tian, X.-J.; Feng, S.-Y.; Li, S.-J.; Li, Z.-W.; Lu, C.-H.; Li, C.-J.; Liu, W.-D. Org. Lett. 2021, 23, 692. |
| [52] | Zhang, K.; Qiao, L.; Xie, J.-W.; Lin, Z.-W.; Li, H.-J.; Lv, P.; Wang, Y.-G. J. Org. Chem. 2021, 86, 9552. |
| [53] | Jin, C.; Yan, Z.-Y.; Sun, B.; Yang, J. Org. Lett. 2019, 21, 2064. |
| [54] | Tan, Y.-S.; Kun, W.-X.; Han, Y.-P.; Zhang, Y.-C.; Zhang, H.-Y.; Zhao, J.-Q. J. Org. Chem. 2022, 87, 8551. |
| [55] | Hua, H.-L.; Wang, G.-P.; Cheng, J.-L.; Liang, Y.-M.; Zhao, J.-H. Asian J. Org. Chem. 2022, 11, e202100726. |
| [56] | Cao, C.-L.; Zhang, G.-X.; Xue, F.; Deng, H.-P. Org. Chem. Front. 2022, 9, 959. |
| [57] | Dey, J.; Paul, S.; Bhakat, M.; Guin, J. Org. Lett. 2022, 24, 8047. |
| [58] | Zhang, L.; Pfund, B.; Wenger, O. S.; Hu, X.-L. Angew. Chem. Int. Ed. 2022, 61, e202202649. |
| [59] | Xu, S.; Ping, Y.-Y.; Li, W.; Guo, H.-Y.; Su, Y.-Y.; Li, Z.-Y.; Wang, M.-Y.; Kong, W.-Q. J. Am. Chem. Soc. 2023, 145, 5231. |
| [60] | Wang, M.; Xie, X.-F.; Liu, J.; Wang, L. Eur. J. Org. Chem. 2020, 1534. |
| [61] | Adak, T.; Hoffmann, M.; Witzel, S.; Rudolph, M.; Dreuw, A.; Hashmi, A. S. K. Chem.-Eur. J. 2020, 26, 15573. |
| [62] | Zhang, L.-L.; Yi, H.; Wang, J.; Lei, A.-W. J. Org. Chem. 2017, 82, 10704. |
| [63] | Rodina, L. L.; Azarova, X. V.; Medvedev, J. J.; Semenok, D. V. Nikolaev, V. A. Beilstein J. Org. Chem. 2018, 14, 2250. |
| [64] | Guerra, D. H.; Hlava?ková, A.; Pramthaisong, C.; Vespoli, l.; Pohl, R.; Slanina, T.; Jahn, U. Angew. Chem. Int. Ed. 2019, 58, 12440. |
| [65] | Papadopoulos, G. N.; Kokotou, M. G.; Spiliopoulou, N.; Nikitas, N. F.; Voutyritsa, E.; Tzaras, D. I.; Kaplaneris, N.; Kokotos, C. G. ChemSusChem 2020, 13, 5934. |
| [66] | Ryu, I.; Tani, A.; Fukuyama, T.; Ravelli, D.; Montanaro, S.; Fagnoni, M. Org. Lett. 2013, 15, 2554. |
| [67] | Wan, T.; Capaldo, L.; Laudadio, G.; Nyuchev, A. V.; Rincón, J. A.; García-Losada, P.; Mateos, C.; Frederick, M. O.; Nu?o, M.; No?l, T. Angew. Chem. Int. Ed. 2021, 60, 17893. |
| [68] | Roy, S.; Chatterjee, I. ACS Org. Inorg. Au. 2022, 2, 306. |
| [69] | Jurberg, I. D.; Nome, R. A.; Crespi, S.; Atvars, T. D. Z.; K?nig, B. Adv. Synth. Catal. 2022, 364, 4061. |
| [70] | Ye, B.-H.; Zhao, J.; Zhao, K.; Mekenna, J. M.; Toste, F. D. J. Am. Chem. Soc. 2018, 140, 8350. |
| [71] | Coric, I.; Muller, S.; List, B. J. Am. Chem. Soc. 2010, 132, 17370. |
| [72] | Si, X.-J.; Zhang, L.-M.; Wu, Z.-Z.; Rudolph, M.; Asiri, A. M.; Hashmi, A. S. K. Org. Lett. 2020, 22, 584. |
| [73] | Spiliopoulou, N.; Koutoulogenis, G S.; Kokotos, C G. Photochem. Photobiol. Sci. 2022, 21, 687. |
| [74] | Zhu, X.-J.; Xie, X.-Y.; Li, P.-H.; Guo, J.-Q.; Wang, L. Org. Lett. 2016, 18, 1546. |
| [75] | Uchikura, T.; Hara, Y.; Tsubono, K.; Akiyama, T. ACS Org. Inorg. Au. 2021, 1, 23. |
| [76] | Liu, B.; Lim, C.-H.; Miyake, G. M. J. Am. Chem. Soc. 2017, 139, 13616. |
| [77] | Li, T.; Liang, K.-J.; Tang, J.-Y.; Ding, Y.-Z.; Xia, C.-F. Chem. Sci. 2021, 12, 15655. |
| [78] | Niu, B.; Sachidanandan, K.; Cooke, M. V.; Casey, T. E.; Laulhé, S. Org. Lett. 2022, 24, 4524. |
| [79] | Wu, J.-W.; Zhou, Y.; Zhou, Y.-C.; Chiang, C. W.; Lei, A.-W. ACS Catal. 2017, 7, 8320. |
| [80] | Huang, R.-L.; Yu, C.-J.; Patureau, F. W. ChemElectroChem 2021, 8, 3943. |
| [81] | Wang, Z.; Liu, Y.-X.; Song, H.-J.; Wang, Q.-M. Green Chem. 2023, 25, 1970. |
| [82] | Huang, H.; Strater, Z. M.; Lambert, T. H. J. Am. Chem. Soc. 2020, 142, 1698. |
| [83] | Xu, P.; Chen, P.-Y.; Xu, H.-C. Angew. Chem. Int. Ed. 2020, 59, 14275. |
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