可见光媒介的C—S键构建反应研究进展
收稿日期: 2023-01-07
修回日期: 2023-02-20
网络出版日期: 2023-03-31
基金资助
吉林化工学院科学技术研究(2020021); 吉林化工学院重大科技(2020010); 吉林化工学院博士启动(2021016); 兴辽英才计划(XLYC1902111); 辽宁省教育厅重点(LZD202005); 吉林省产业技术研究与开发(2020C028-1); 吉林省科技发展计划(202002008JC)
Recent Progress in the C—S Bond Formation Reactions Mediated by Visible Light
Received date: 2023-01-07
Revised date: 2023-02-20
Online published: 2023-03-31
Supported by
Science and Technology Research Project of Jilin Institute of Chemical Technology(2020021); Major Scientific and Technological Projects of Jilin Institute of Chemical Technology(2020010); Doctoral Start-up Foundation of Jilin Institute of Chemical Technology(2021016); Liaoning Revitalization Talents Program(XLYC1902111); Key Projects of Department of Education of Liaoning Province(LZD202005); Research and Development Project for Industrial Technology of Jilin Province(2020C028-1); Science and Technology Development of Jilin Province(202002008JC)
吴敏 , 刘博 , 袁佳龙 , 付强 , 汪锐 , 娄大伟 , 梁福顺 . 可见光媒介的C—S键构建反应研究进展[J]. 有机化学, 2023 , 43(7) : 2269 -2292 . DOI: 10.6023/cjoc202301006
The construction of C—S bond is of great significance in organic synthesis, in viewing that organic compounds containing C—S bonds are widely present in various natural products, drugs and functional materials. At present, transition metal-catalyzed C—S bond formation reactions have been well developed. However, in recent years, the visible-light-mediated C—S bond formation reactions have received more and more attention due to the characteristics of milder conditions, greener and higher reactivity. According to the classification of the reaction mechanisms, the methods of C—S bond construction based on photo-mediated redox catalysis, electron donor-acceptor complexes and energy transfer are summarized and a future perspective is made.
| [1] | Ciamician, G. Science 1912, 36, 385. |
| [2] | (a) Zhu, H.-Z.; Dronamraju, V.; Xie, W.; More, S. S. Med. Chem. Res. 2021, 30, 305. |
| [2] | (b) Wang, N.-Z.; Saidhareddy, P.; Jiang, X.-F. Nat. Prod. Rep. 2020, 37, 246. |
| [2] | (c) Nicastro, H. L.; Ross, S. A.; Milner, J. A. Cancer Prev. Res. 2015, 8, 181. |
| [2] | (d) Jacob, C. Nat. Prod. Rep. 2006, 23, 851. |
| [3] | (a) Feng, M.-H.; Tang, B.-Q.; Liang, S. H.; Jiang, X.-F. Curr. Top. Med. Chem. 2016, 16, 1200. |
| [3] | (b) Mustafa, M.; Winum, J. Y. Expert Opin. Drug Discovery 2022, 17, 501. |
| [4] | (a) Boyd, D. A. Angew. Chem., Int. Ed. 2016, 55, 15486. |
| [4] | (b) Rahate, A. S.; Nemade, K. R.; Waghuley, S. A. Rev. Chem. Eng. 2013, 29, 471. |
| [5] | (a) Su, Y.; Zhou, X.-J.; He, C.-L.; Zhang, W.; Ling, X.; Xiao, X. J. Org. Chem. 2016, 81, 4981. |
| [5] | (b) Yang, Y.; Zhang, S.; Tang, L.; Hu, Y.-B.; Zha, Z.-G.; Wang, Z. Green Chem. 2016, 18, 2609. |
| [5] | (c) Yu, J.-Q.; Ding, K.-L. Acta Chim. Sinica 2015, 73, 1223 (in Chinese). |
| [5] | (余金权, 丁奎岭, 化学学报, 2015, 73, 1223.) |
| [5] | (d) Sun, F.-L.; Liu, X.-M.; Chen, X.-Z.; Qian, C.; Ge, X. Chin. J. Org. Chem. 2017, 37, 2211 (in Chinese). |
| [5] | (孙丰莉, 刘学民, 陈新志, 钱超, 葛新, 有机化学, 2017, 37, 2211.) |
| [6] | (a) Varun, B. V.; Prabhu, K. R. J. Org. Chem. 2014, 79, 9655. |
| [6] | (b) Hostier, T.; Ferey, V.; Ricci, G.; Gomez Pardo, D.; Cossy, J. Chem. Commun. 2015, 51, 13898. |
| [7] | (a) Carril, M.; SanMartin, R.; Dominguez, E.; Tellitu, I. Chem.-Eur. J. 2007, 13, 5100. |
| [7] | (b) Kabir, M. S.; Linn, M. L. V.; Monte, A.; Cook, J. M. Org. Lett. 2008, 10, 3363. |
| [7] | (c) Zhu, W.; Ma, D.-W. J. Org. Chem. 2004, 70, 2696. |
| [8] | (a) Ranjit, S.; Duan, Z.; Zhang, P.; Liu, X. Org. Lett. 2010, 12, 4134. |
| [8] | (b) Nilsson, M.; Kulonen, E.; Sunner, S.; Frank, V.; Brunvoll, J.; Bunnenberg, E.; Djerassi, C.; Records, R. Acta Chem. Scand. 1966, 20, 423. |
| [8] | (c) Suzuki, H.; Abe, H. Tetrahedron Lett. 1995, 36, 6239. |
| [8] | (d) Qin, Y.-C.; Peng, Q. Chin. J. Org. Chem. 2011, 31, 1169 (in Chinese). |
| [8] | (秦元成, 彭强, 有机化学, 2011, 31, 1169.) |
| [9] | Wang, H.-B.; Wang, L.; Shang, J.-S.; Li, X.; Wang, H.-Y.; Gui, J.; Lei, A.-W. Chem. Commun. 2012, 48, 76. |
| [10] | Wang, P.-F.; Wang, X.-Q.; Dai, J.-J.; Feng, Y.-S.; Xu, H.-J. Org. Lett. 2014, 16, 4586. |
| [11] | Lan, M.-T.; Wu, W.-Y.; Huang, S.-H.; Luo, K.-L.; Tsai, F.-Y. RSC Adv. 2011, 1,1151. |
| [12] | Liu, T.-J.; Yi, C.-L.; Chan, C.-C.; Lee, C.-F. Chem.-Asian J. 2013, 8, 1029. |
| [13] | (a) Zhu, J.-Y.; Chen, Y.; Lin, F.; Wang, B.-S.; Chen, Z.-W.; Liu, L.-X. Org. Biomol. Chem. 2015, 13, 3711. |
| [13] | (b) Brigham, C. E.; Malapit, C. A.; Lalloo, N.; Sanford, M. S. ACS Catal. 2020, 10, 8315. |
| [14] | Tavares Junior, J.; da Silva, C. D. G.; Dos Santos, B. F.; Souza, N. S.; Oliveira, A. R. D.; Kupfer, V. L.; Rinaldi, A. W.; Domingues, N. L. C. Org. Biomol. Chem. 2019, 17, 10103. |
| [15] | Reddy, V. P.; Swapna, K.; Kumar, A. V.; Rao, K. R. J. Org. Chem. 2008, 74, 3189. |
| [16] | Timpa, S. D.; Pell, C. J.; Ozerov, O. V. J. Am. Chem. Soc. 2014, 136, 14772. |
| [17] | (a) Shang, R.; Liu, L. Sci. China: Chem. 2011, 54, 1670. |
| [17] | (b) Ganley, J. M.; Yeung, C. S. J. Org. Chem. 2017, 82, 13557. |
| [17] | (c) Becht, J. M.; Le Drian, C. J. Org. Chem. 2011, 76, 6327. |
| [18] | (a) Wimmer, A.; Konig, B. Beilstein J. Org. Chem. 2018, 14, 54. |
| [18] | (b) Gao, J.; Feng, J.; Du, D. Chem.-Asian. J. 2020, 15, 3637. |
| [19] | (a) Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1. |
| [19] | (b) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. Chem. Rev. 2013, 113, 5322. |
| [19] | (c) Narayanam, J. M.; Stephenson, C. R. Chem. Soc. Rev. 2011, 40, 102. |
| [19] | (d) Chen, J.-R.; Yan, D.-M.; Wei, Q.; Xiao, W.-J. ChemPhotoChem 2017, 1, 148. |
| [19] | (e) Xue, D.; Song, G.-Y. Chin. J. Org. Chem. 2022, 42, 2275 (in Chinese). |
| [19] | (宋戈洋, 薛东, 有机化学, 2022, 42, 2275.) |
| [20] | Yan, D.-M.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2019, 58, 378. |
| [21] | Chen, M.; Huang, Z.-T.; Zheng, Q.-Y. Chem. Commun. 2012, 48, 11686. |
| [22] | Penteado, F.; Gomes, C. S.; Monzon, L. I.; Perin, G.; Silveira, C. C.; Lenard?o, E. J. Eur. J. Org. Chem. 2020, 2020, 2110. |
| [23] | Tyson, E. L.; Ament, M. S.; Yoon, T. P. J. Org. Chem. 2013, 78, 2046. |
| [24] | Zhao, G.-Y.; Kaur, S.; Wang, T. Org. Lett. 2017, 19, 3291. |
| [25] | Wang, J.-L.; Huang, B.-B.; Yang, C.; Xia, W.-J. Chem. Commun. 2019, 55, 11103. |
| [26] | Wang, X.; Cuny, G. D.; Noel, T. Angew. Chem., Int. Ed. 2013, 52, 7860 |
| [27] | Jiang, M.; Li, H.-F.; Yang, H.-J.; Fu, H. Angew. Chem., Int. Ed. 2017, 56, 874 |
| [28] | Li, J.; Bao, W.-H.; Zhang, Y.; Rao, Y.-J. Eur. J. Org. Chem. 2019, 2019, 7175. |
| [29] | Zubkov, M. O.; Kosobokov, M. D.; Levin, V. V.; Dilman, A. D. Org. Lett. 2022, 24, 2354. |
| [30] | Jeremy, D. G.; Mary, A. Z.; Nicewicz, D. A. J. Am. Chem. Soc. 2015, 137, 11340. |
| [31] | Jiang, H.; Chen, X.-J.; Zhang, Y.; Yu, S.-Y. Adv. Synth. Catal. 2013, 355, 809. |
| [32] | Meyer, A. U.; J?ger, S.; Hari, D. P.; K?nig, B. Adv. Synth. Catal. 2015, 357, 2050. |
| [33] | Kumar, J.; Ahmad, A.; Rizvi, M. A.; Ganie, M. A.; Khajuria, C.; Shah, B. A. Org. Lett. 2020, 22, 5661. |
| [34] | Liang, G.; Wang, J.-H.; Lei, A.; Cheng, Y.-Y.; Zhou, C.; Chen, Y.-J.; Ye, C.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Org. Lett. 2021, 23, 8082. |
| [35] | Rahaman, R.; Hoque, M. T.; Maiti, D. K. Org. Lett. 2022, 24, 6885. |
| [36] | Wang, P.; Zhang, H.; Nie, X.; Xu, T.; Liao, S.-H. Nat. Commun. 2022, 13, 3370. |
| [37] | Nie, X.-L.; Xu, T.-X.; Song, J.-S.; Devaraj, A.; Zhang, B.-L.; Chen, Y.; Liao, S.-H. Angew. Chem., Int. Ed. 2021, 60, 3956. |
| [38] | Yadav, A. K.; Yadav, L. D. S. Tetrahedron Lett. 2015, 56, 6696. |
| [39] | Tan, W.; Wang, C.-H.; Jiang, X.-F. Chin. J. Chem. 2019, 37, 1234. |
| [40] | Chen, Z.-R.; Jin, W.-W.; Xia, Y.; Zhang, Y.-H.; Xie, M.-W.; Ma, S.-C.; Liu, C.-J. Org. Lett. 2020, 22, 8261. |
| [41] | Ghosh, K. G.; Das, D.; Garai, S.; Chandu, P.; Sureshkumar, D. J. Org. Chem. 2022, 87, 8611. |
| [42] | (a) Mulliken, R. S. J. Phys. Chem. 1952, 56, 801. |
| [42] | (b) Esrafili, M. D. J. Mol. Model. 2013, 19, 1417. |
| [42] | (c) Mulliken, R. S. J. Am. Chem. Soc. 1950, 72, 600. |
| [43] | (a) Andrews, L. J. Chem. Rev. 1954, 54, 713. |
| [43] | (b) Foster, R. J. Phys. Chem. 1980, 84, 2135. |
| [44] | Fox, M.; Younathan, J. N.; Fryxell, G. J. Org. Chem. 1983, 15, 3109. |
| [45] | Sankararaman, S.; Haney, W. A.; Kochi, J. K. J. Am. Chem. Soc. 1987, 109, 7824. |
| [46] | (a) Crisenza, G. E. M.; Mazzarella, D.; Melchiorre, P. J. Am. Chem. Soc. 2020, 142, 5461. |
| [46] | (b) Kale, M. J.; Avanesian, T.; Christopher, P. ACS Catal. 2013, 4, 116. |
| [47] | Rosokha, S. V.; Kochi, J. K. Acc. Chem. Res. 2008, 41, 641. |
| [48] | Liu, B.; Lim, C.-H.; Miyake, G. M. J. Am. Chem. Soc. 2017, 139, 13616. |
| [49] | Uchikura, T.; Hara, Y.; Tsubono, K.; Akiyama, T. ACS Org. Inorg. Au 2021, 1, 23. |
| [50] | Li, Y.; Miao, T.; Li, P.; Wang, L. Org. Lett. 2018, 20, 1735. |
| [51] | Ho, H. E.; Pagano, A.; Rossi-Ashton, J. A.; Donald, J. R.; Epton, R. G.; Churchill, J. C.; James, M. J.; O'Brien, P.; Taylor, R. J. K.; Unsworth, W. P. Chem. Sci. 2019, 11, 1353. |
| [52] | Yang, M.-C.; Cao, T.-P.; Xu, T.-X.; Liao, S.-H. Org. Lett. 2019, 21, 8673. |
| [53] | Li, Y.; Ma, F.; Li, P.-H.; Miao, T.; Wang, L. Adv. Synth. Catal. 2019, 361, 1606. |
| [54] | Cai, Y.; Nie, F.-Y.; Song, Q.-H. J. Org. Chem. 2021, 86, 12419. |
| [55] | Sundaravelu, N.; Nandy, A.; Sekar, G. Org. Lett. 2021, 23, 3115. |
| [56] | Liang, X.; Li, Y.-F.; Xia, Q.; Cheng, L.; Guo, J.-B.; Zhang, P.; Zhang, W.-H.; Wang, Q.-M. Green Chem. 2021, 23, 8865. |
| [57] | Chen, Z.-R.; Xue, F.; Liu, T.-X.; Wang, B.; Zhang, Y.-H.; Jin, W.-W.; Xia, Y.; Liu, C.-J. Green Chem. 2022, 24, 3250. |
| [58] | Chen, Z.-R.; Xue, F.; Zhang, Y.-H.; Jin, W.-W.; Wang, B.; Xia, Y.; Xie, M.-W.; Abdukader, A.; Liu, C.-J. Org. Lett. 2022, 24, 3149. |
| [59] | Wu, Q.; Zhao, Y.-H.; Chai, L.-L.; Li, H.-Y.; Li, H.-X. Org. Chem. Front. 2022, 9, 2977. |
| [60] | Xie, W.-J.; Ma, P.-J.; Zhang, Y.-J.; Xi, L.-Y.; Qiu, S.-Q.; Huang, X.; Yang, B.; Gao, Y.; Zhang, J.-M. Org. Lett. 2022, 24, 6099. |
| [61] | Granados, A.; Cabrera-Afonso, M. J.; Escolano, M.; Badir, S. O.; Molander, G. A. Chem. Catal. 2022, 2, 898. |
| [62] | Zhang, Y.; Xia, S.-D.; Shi, W.-X.; Lin, B.-Z.; Su, X.-C.; Lu, W.-W.; Wu, X.-Y.; Wang, X.; Lu, X.-J.; Yan, M.; Zhang, X.-J. Org. Lett. 2022, 24, 7961. |
| [63] | Cabrera-Afonso, M. J.; Granados, A.; Molander, G. A. Angew Chem., Int. Ed. 2022, 61, 1. |
| [64] | (a) Skourtis, S. S.; Liu, C.; Antoniou, P.; Virshup, A. M.; Beratan, D. N. Proc. Natl. Acad. Sci. U. S. A. 2016, 113, 8115. |
| [64] | (b) Scholes, G. D. Annu. Rev. Phys. Chem. 2003, 54, 57. |
| [64] | (c) Scandola, F.; Indelli, M. T.; Chiorboli, C.; Bignozzi, C. A. Top. Curr. Chem. 1990, 158, 75. |
| [65] | (a) Garcia-Parajo, M. F.; Hernando, J.; Sanchez Mosteiro, G.; Hoogenboom, J. P.; van Dijk, E. M.; van Hulst, N. F. ChemPhys- Chem 2005, 6, 819. |
| [65] | (b) Porter, G. B. Adv. Photochem. 1974, 9, 148. |
| [66] | Grosskopf, J.; Kratz, T.; Rigotti, T.; Bach, T. Chem. Rev. 2022, 122, 1626. |
| [67] | Xiao, W.-J.; Zhou, Q.-Q.; Zou, Y.-Q.; Lu, L.-Q. Angew. Chem., Int. Ed. 2018, 58, 1586. |
| [68] | Marzo, L.; Pagire, S. K.; Reiser, O.; Konig, B. Angew. Chem., Int. Ed. 2018, 57, 10034. |
| [69] | Zhu, S.; Pathigoolla, A.; Lowe, G.; Walsh, D. A.; Cooper, M.; Lewis, W.; Lam, H. W. Chem.-Eur. J. 2017, 23, 17598. |
| [70] | Li, Y.-M.; Wang, M.; Jiang, X.-F. ACS Catal. 2017, 7, 7587. |
| [71] | Teders, M.; Henkel, C.; Anhauser, L.; Strieth-Kalthoff, F.; Gomez- Suarez, A.; Kleinmans, R.; Kahnt, A.; Rentmeister, A.; Guldi, D.; Glorius, F. Nat. Chem. 2018, 10, 981. |
| [72] | Escobar, R. A.; Johannes, J. W. Chem.-Eur. J. 2020, 26, 5168. |
| [73] | Gadde, K.; Mampuys, P.; Guidetti, A.; Ching, H. Y. V.; Herrebout, W. A.; Van Doorslaer, S.; Abbaspour Tehrani, K.; Maes, B. U. W. ACS Catal. 2020, 10, 8765. |
| [74] | (a) Gravatt, C. S.; Johannes, J. W.; King, E. R.; Ghosh, A. J. Org. Chem. 2022, 87, 8921. |
| [74] | (b) Huang, S.; Wang, M.; Jiang, X.-F. Chem. Soc. Rev. 2022, 51, 8351. |
| [75] | Xu, T.-X.; Cao, T.-P.; Yang, M.-C.; Xu, R.-T.; Nie, X.-L.; Liao, S.-H. Org. Lett. 2020, 22, 3692. |
| [76] | (a) Li, H.-Y.; Cheng, Z.-R.; Tung, C.-H.; Xu, Z.-H. ACS Catal. 2018, 8, 8237. |
| [76] | (b) Song, T.-T.; Li, H.-Y.; Wei, F.; Tung, C.-H.; Xu, Z.-H. Tetrahedron Lett. 2019, 60, 916. |
| [77] | Jouffroy, M.; Kelly, C. B.; Molander, G. A. Org. Lett. 2016, 18, 876. |
| [78] | Oderinde, M. S.; Frenette, M.; Robbins, D. W.; Aquila, B.; Johannes, J. W. J. Am. Chem. Soc. 2016, 138, 1760. |
| [79] | Santandrea, J.; Minozzi, C.; Cruche, C.; Collins, S. K. Angew. Chem., Int. Ed. 2017, 56, 12255. |
| [80] | Zhong, S.; Zhou, Z.-W.; Zhao, F.; Mao, G.-J.; Deng, G. J.; Huang, H.-W. Org. Lett. 2022, 24, 1865. |
| [81] | Du, H.-W.; Liu, M.-S.; Shu, W. Org. Lett. 2022, 24, 5519. |
| [82] | Wei, L.-D.; Wu, C.-J.; Tung, C.-H.; Wang, W.-G.; Xu, Z.-H. Org. Chem. Front. 2019, 6, 3224. |
| [83] | Fagnoni, M.; Dondi, D.; Ravelli, D.; Albini, A. Chem. Rev. 2007, 107, 2725. |
| [84] | Blanka, L.; Fagnoni, M.; Protti, S.; Rueping, M. Synthesis 2019, 51, 1243. |
| [85] | Wang, H.; Wu, Q.; Zhang, J.-D.; Li, H.-Y.; Li, H.-X. Org. Lett. 2021, 23, 2078. |
/
| 〈 |
|
〉 |