Chinese Journal of Organic Chemistry >
Progress in Visible-Light Promoted Transformations of Organosilicon Compounds
Received date: 2022-12-13
Revised date: 2023-02-23
Online published: 2023-04-14
Supported by
The Natural Science Foundation of Shanxi Province(201901D111081); The Shanxi Scholarship Council of China(2020-029)
Organosilicon compounds play important roles in the fields of material science and pharmaceutical chemistry. The transformations involving organosilicon reagents have therefore attract extensive interest from synthetic community. The burgeoning visible light photocatalysis has provided a new opportunity for organic synthesis. Under the photoredox system, organosilicon compounds could be transformed into silicon or carbon radicals to participate in a variety of reactions. Generally, these reactions bear the merits, such as mild conditions, good selectivity, as well as high atom economy. According to the types of reactions, the recent progress in visible-light mediated hydrosilylation and difunctionalization of alkenes and alkynes, C—H bond silylation of N-aromatic heterocycles using organosilicon compounds as silicon radical precursors, and nucleophilic addition, Minisci reaction, homolytic substitution, as well as transition metal mediated cross-coupling reactions using organosilicon compounds as carbon radical precursors is reviewed primarily herein.
Xiaona Yang , Hongyu Guo , Rong Zhou . Progress in Visible-Light Promoted Transformations of Organosilicon Compounds[J]. Chinese Journal of Organic Chemistry, 2023 , 43(8) : 2720 -2742 . DOI: 10.6023/cjoc202212017
| [1] | Brook, M. A. Silicon in Organic, Organometallic and Polymer Chemistry, John Wiley & Sons, New York, 2000. |
| [2] | (a) Franz, A. K.; Wilson, S. O. J. Med. Chem. 2013, 56, 388. |
| [2] | (b) Li, X.-Y.; Sun, L.; Wu, L.-H. Chin. J. Soil Sci. 2014, 45, 193. (in Chinese) |
| [2] | ( 李晓艳, 孙立, 吴良欢, 土壤通报, 2014, 45, 193.) |
| [3] | (a) Nakao, Y.; Hiyama, T. Chem. Soc. Rev. 2011, 40, 4893. |
| [3] | (b) Luo, H.; Zhang, Z.; Liu, H.; Liu, J. Chin. J. Org. Chem. 2015, 35, 802. (in Chinese) |
| [3] | ( 罗海清, 张志鹏, 刘海东, 柳辉金, 有机化学, 2015, 35, 802.) |
| [4] | (a) Murray, P. R. D.; Cox, J. H.; Chiappini, N. D.; Roos, C. B.; McLoughlin, E. A.; Hejna, B. G.; Nguyen, S. T.; Ripberger, H. H.; Ganley, J. M.; Tsui, E.; Shin, N. Y.; Koronkiewicz, B.; Qiu, G.; Knowles, R. R. Chem. Rev. 2022, 122, 2017. |
| [4] | (b) Holmberg-Douglas, N.; Nicewicz, D. A. Chem. Rev. 2022, 122, 1925. |
| [4] | (c) Buglioni, L.; Raymenants, F.; Slattery, A.; Zondag, S. D. A.; No?l, T. Chem. Rev. 2022, 122, 2752. |
| [4] | (d) Coppola, G. A.; Pillitteri, S.; Van der Eycken, E. V.; You, S.-L.; Sharma, U. K. Chem. Soc. Rev. 2022, 51, 2313. |
| [4] | (e) Chang, L.; An, Q.; Duan, L.; Feng, K.; Zuo, Z. Chem. Rev. 2022, 122, 2429. |
| [4] | (f) Capaldo, L.; Ravelli, D.; Fagnoni, M. Chem. Rev. 2022, 122, 1875. |
| [4] | (g) Cheung, K. P. S.; Sarkar, S.; Gevorgyan, V. Chem. Rev. 2022, 122, 1543. |
| [4] | (h) Kwon, K.; Simons, R. T.; Nandakumar, M.; Roizen, J. L. Chem. Rev. 2022, 122, 2353. |
| [4] | (i) Xu, J.; Cao, J.; Wu, X.; Wang, H.; Yang, X.; Tang, X.; Toh, R. W.; Zhou, R.; Yeow, E. K. L.; Wu, J. J. Am. Chem. Soc. 2021, 143, 13266. |
| [4] | (j) Zhou, R.; Liu, H.; Tao, H.; Yu, X.; Wu, J. Chem. Sci. 2017, 8, 4654. |
| [5] | (a) Ren, L.-Q.; Li, N.; Ke, J.; He, C. Org. Chem. Front. 2022, 9, 6400. |
| [5] | (b) Li, J.-S.; Wu, J. ChemPhotoChem 2018, 2, 839. |
| [6] | Qrareya, H.; Dondi, D.; Ravelli, D.; Fagnoni, M. ChemCatChem 2015, 7, 3350. |
| [7] | Zhou, R.; Goh, Y. Y.; Liu, H.; Tao, H.; Li, L.; Wu, J. Angew. Chem., Int. Ed. 2017, 56, 16621. |
| [8] | Roberts, B. P. Chem. Soc. Rev. 1999, 28, 25. |
| [9] | Wan, Y.; Zhu, J.; Yuan, Q.; Wang, W.; Zhang, Y. Org. Lett. 2021, 23, 1406. |
| [10] | Cai, Y.; Zhao, W.; Wang, S.; Liang, Y.; Yao, Z.-J. Org. Lett. 2019, 21, 9836. |
| [11] | Zhu, J.; Cui, W.-C.; Wang, S.; Yao, Z.-J. J. Org. Chem. 2018, 83, 14600. |
| [12] | Cui, W. C.; Zhao, W.; Gao, M.; Liu, W.; Wang, S.; Liang, Y.; Yao, Z. J. Chem.-Eur. J. 2019, 25, 16506. |
| [13] | Zhu, J.; Cui, W.-C.; Wang, S.; Yao, Z.-J. Org. Lett. 2018, 20, 3174. |
| [14] | Liang, H.; Ji, Y.-X.; Wang, R.-H.; Zhang, Z.-H.; Zhang, B. Org. Lett. 2019, 21, 2750. |
| [15] | Xu, N.-X.; Li, B.-X.; Wang, C.; Uchiyama, M. Angew. Chem., Int. Ed. 2020, 59, 10639. |
| [16] | Zhong, M.; Pannecoucke, X.; Jubault, P.; Poisson, T. Chem.-Eur. J. 2021, 27, 11818. |
| [17] | Takemura, N.; Sumida, Y.; Ohmiya, H. ACS Catal. 2022, 12, 7804. |
| [18] | Arai, R.; Nagashima, Y.; Koshikawa, T.; Tanaka, K. J. Org. Chem. 2022, 10.1021/acs.joc.2c01885. |
| [19] | Wan, Y.; Zhao, Y.; Zhu, J.; Yuan, Q.; Wang, W.; Zhang, Y. Green Chem. 2023, 25, 256. |
| [20] | Liu, R.; Chia, S. P. M.; Goh, Y. Y.; Cheo, H. W.; Fan, B.; Li, R.; Zhou, R.; Wu, J. Eur. J. Org. Chem. 2020, 2020, 1459. |
| [21] | Yu, X.; Lübbesmeyer, M.; Studer, A. Angew. Chem., Int. Ed. 2021, 60, 675. |
| [22] | Hou, J.; Ee, A.; Cao, H.; Ong, H. W.; Xu, J. H.; Wu, J. Angew. Chem., Int. Ed. 2018, 57, 17220. |
| [23] | Zheng, M.; Hou, J.; Hua, L. L.; Tang, W. Y.; Zhan, L. W.; Li, B. D. Org. Lett. 2021, 23, 5128. |
| [24] | Neogi, S.; Kumar Ghosh, A.; Mandal, S.; Ghosh, D.; Ghosh, S.; Hajra, A. Org. Lett. 2021, 23, 6510. |
| [25] | Zheng, W.; Xu, Y.; Luo, H.; Feng, Y.; Zhang, J.; Lin, L. Org. Lett. 2022, 24, 7145. |
| [26] | Ploger, S.; Studer, A. Org. Lett. 2022, 24, 8568. |
| [27] | Zhang, Z.; Hu, X. ACS Catal. 2019, 10, 777. |
| [28] | (a) Lu, B.; Falck, J. R. Angew. Chem., Int. Ed. 2008, 47, 7508. |
| [28] | (b) Cheng, C.; Hartwig, J. F. Science 2014, 343, 853. |
| [28] | (c) Cheng, C.; Hartwig, J. F. J. Am. Chem. Soc. 2015, 137, 592. |
| [28] | (d) Devaraj, K.; Sollert, C.; Juds, C.; Gates, P. J.; Pilarski, L. T. Chem. Commun. 2016, 52, 5868. |
| [29] | (a) Klare, H. F. T.; Oestreich, M.; Ito, J.-i.; Nishiyama, H.; Ohki, Y.; Tatsumi, K. J. Am. Chem. Soc. 2011, 133, 3312. |
| [29] | (b) Wübbolt, S.; Oestreich, M. Angew. Chem., Int. Ed. 2015, 54, 15876. |
| [29] | (c) Chen, Q.-A.; Klare, H. F. T.; Oestreich, M. J. Am. Chem. Soc. 2016, 138, 7868. |
| [29] | (d) B?hr, S.; Oestreich, M. Angew. Chem., Int. Ed. 2017, 56, 52. |
| [30] | (a) Toutov, A. A.; Liu, W.-B.; Betz, K. N.; Fedorov, A.; Stoltz, B. M.; Grubbs, R. H. Nature 2015, 518, 80. |
| [30] | (b) Banerjee, S.; Yang, Y.-F.; Jenkins, I. D.; Liang, Y.; Toutov, A. A.; Liu, W.-B.; Schuman, D. P.; Grubbs, R. H.; Stoltz, B. M.; Krenske, E. H.; Houk, K. N.; Zare, R. N. J. Am. Chem. Soc. 2017, 139, 6880. |
| [31] | (a) Proctor, R. S. J.; Phipps, R. J. Angew. Chem., Int. Ed. 2019, 58, 13666. |
| [31] | (b) Dong, J.; Liu, Y.; Wang, Q. Chin. J. Org. Chem. 2021, 41, 3771. (in Chinese) |
| [31] | ( 董建洋, 刘玉秀, 汪清民, 有机化学, 2021, 41, 3771.) |
| [31] | (c) Meng, W.; Xu, K.; Guo, B.; Zeng, C. Chin. J. Org. Chem. 2021, 41, 2621. (in Chinese) |
| [31] | ( 孟薇, 徐坤, 郭兵兵, 曾程初, 有机化学, 2021, 41, 2621.) |
| [32] | Liu, S.; Pan, P.; Fan, H.; Li, H.; Wang, W.; Zhang, Y. Chem. Sci. 2019, 10, 3817. |
| [33] | Rammal, F.; Gao, D.; Boujnah, S.; Hussein, A. A.; Lalevée, J.; Gaumont, A.-C.; Morlet-Savary, F.; Lakhdar, S. ACS Catal. 2020, 10, 13710. |
| [34] | Dai, C.; Zhan, Y.; Liu, P.; Sun, P. Green. Chem. 2021, 23, 314. |
| [35] | Fan, X.; Xiao, P.; Jiao, Z.; Yang, T.; Dai, X.; Xu, W.; Tan, J. D.; Cui, G.; Su, H.; Fang, W.; Wu, J. Angew. Chem., Int. Ed. 2019, 58, 12580. |
| [36] | Zhou, R.; Ma, L.; Yang, X.; Cao, J. Org. Chem. Front. 2021, 8, 426. |
| [37] | Zhou, R.; Li, J.; Cheo, H. W.; Chua, R.; Zhan, G.; Hou, Z.; Wu, J. Chem. Sci. 2019, 10, 7340. |
| [38] | Cao, J.; Yang, X.; Ma, L.; Lu, K.; Zhou, R. Green Chem. 2021, 23, 8988. |
| [39] | Gan, Q.-C.; Song, Z.-Q.; Tung, C.-H.; Wu, L.-Z. Org. Lett. 2022, 24, 5192. |
| [40] | Silvi, M.; Verrier, C.; Rey, Y. P.; Buzzetti, L.; Melchiorre, P. Nat. Chem. 2017, 9, 868. |
| [41] | Uygur, M.; Danelzik, T.; García Manche?o, O. Chem. Commun. 2019, 55, 2980. |
| [42] | Khatun, N.; Kim, M. J.; Woo, S. K. Org. Lett. 2018, 20, 6239. |
| [43] | Sch?fers, F.; Dutta, S.; Kleinmans, R.; Mück-Lichtenfeld, C.; Glorius, F. ACS Catal. 2022, 12, 12281. |
| [44] | Ghiazza, C.; Khrouz, L.; Billard, T.; Monnereau, C.; Tlili, A. Eur. J. Org. Chem. 2020, 2020, 1559. |
| [45] | (a) Corcé, V.; Chamoreau, L.-M.; Derat, E.; Goddard, J.-P.; Ollivier, C.; Fensterbank, L. Angew. Chem., Int. Ed. 2015, 54, 11414. |
| [45] | (b) Yoshida, J.-I.; Tamao, K.; Kakui, T.; Kurita, A.; Murata, M.; Yamada, K.; Kumada, M. Organometallics 1982, 1, 369. |
| [46] | Nishigaichi, Y.; Suzuki, A.; Saito, T.; Takuwa, A. Tetrahedron Lett. 2005, 46, 5149. |
| [47] | Patel, N. R.; Kelly, C. B.; Siegenfeld, A. P.; Molander, G. A. ACS Catal. 2017, 7, 1766. |
| [48] | (a) Phelan, J. P.; Lang, S. B.; Compton, J. S.; Kelly, C. B.; Dykstra, R.; Gutierrez, O.; Molander, G. A. J. Am. Chem. Soc. 2018, 140, 8037. |
| [48] | (b) Milligan, J. A.; Phelan, J. P.; Polites, V. C.; Kelly, C. B.; Molander, G. A. Org. Lett. 2018, 20, 6840. |
| [48] | (c) Luo, W.; Yang, Y.; Fang, Y.; Zhang, X.; Jin, X.; Zhao, G.; Zhang, L.; Li, Y.; Zhou, W.; Xia, T.; Chen, B. Adv. Synth. Catal. 2019, 361, 4215. |
| [48] | (d) Luo, W.; Fang, Y.; Zhang, L.; Xu, T.; Liu, Y.; Li, Y.; Jin, X.; Bao, J.; Wu, X.; Zhang, Z. Eur. J. Org. Chem. 2020, 2020, 1778. |
| [48] | (e) Milligan, J. A.; Burn, K. L.; Le, A. V.; Polites, V. C.; Wang, Z.-J.; Molander, G. A.; Kelly, C. B. Adv. Synth. Catal. 2020, 362, 242. |
| [49] | Pantaine, L. R. E.; Milligan, J. A.; Matsui, J. K.; Kelly, C. B.; Molander, G. A. Org. Lett. 2019, 21, 2317. |
| [50] | Cartier, A.; Levernier, E.; Corcé, V.; Fukuyama, T.; Dhimane, A.-L.; Ollivier, C.; Ryu, I.; Fensterbank, L. Angew. Chem., Int. Ed. 2019, 58, 1789. |
| [51] | Cartier, A.; Levernier, E.; Dhimane, A.-L.; Fukuyama, T.; Ollivier, C.; Ryu, I.; Fensterbank, L. Adv. Synth. Catal. 2020, 362, 2254. |
| [52] | Ikarashi, G.; Morofuji, T.; Kano, N. Chem. Commun. 2020, 56, 10006. |
| [53] | Wang, Z.-J.; Zheng, S.; Matsui, J. K.; Lu, Z.; Molander, G. A. Chem. Sci. 2019, 10, 4389. |
| [54] | Wang, F.; Wang, S.-Y. Org. Chem. Front. 2021, 8, 1976. |
| [55] | (a) Patel, N. R.; Kelly, C. B.; Jouffroy, M.; Molander, G. A. Org. Lett. 2016, 18, 764. |
| [55] | (b) Patel, N. R.; Molander, G. A. J. Org. Chem. 2016, 81, 7271. |
| [56] | Lévêque, C.; Chenneberg, L.; Corcé, V.; Ollivier, C. Fensterbank, L. Chem. Commun. 2016, 52, 9877. |
| [57] | Schirmer, T. E.; Abdellaoui, M.; Savateev, A.; Ollivier, C.; Antonietti, M.; Fensterbank, L.; K?nig, B. Org. Lett. 2022, 24, 2483. |
| [58] | Lévêque, C.; Corcé, V.; Chenneberg, L.; Ollivier, C.; Fensterbank, L. Eur. J. Org. Chem. 2017, 2017, 2118. |
| [59] | Levernier, E.; Corcé, V.; Rakotoarison, L.-M.; Smith, A.; Zhang, M.; Ognier, S.; Tatoulian, M.; Ollivier, C.; Fensterbank, L. Org. Chem. Front. 2019, 6, 1378. |
| [60] | (a) Jouffroy, M.; Primer, D. N.; Molander, G. A. J. Am. Chem. Soc. 2016, 138, 475. |
| [60] | (b) Gutierrez, O.; Tellis, J. C.; Primer, D. N.; Molander, G. A.; Kozlowski, M. C. J. Am. Chem. Soc. 2015, 137, 4896. |
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