Chinese Journal of Organic Chemistry >
Recent Progress in Radical-Mediated Si—H Functionalization of Silanes: An Effective Strategy for the Synthesis of Organosilanes Containing C—Si Bond
Received date: 2022-07-31
Revised date: 2022-08-28
Online published: 2022-09-23
Supported by
National Natural Science Foundation of China(21871067); National Natural Science Foundation of China(22271069); Natural Science Foundation of Guangdong Province(2021A1515010190); Open Project Program of State Key Laboratory of Elemento-Organic Chemistry(202009); Guangdong Provincial Key Laboratory of Catalysis(2020B121201002); Fundamental Research Funds for the Central Universities(HIT.OCEF.2021035)
Organosilanes are versatile intermediates and products in material chemistry, pharmaceutical chemistry and synthetic chemistry because of their unique physical, chemical and physiological properties. In the past century, the synthesis of organosilanes containing C—Si bonds has gradually become one of the research hotspots. Due to the high tolerance of functional groups, good atomic economy and chemoselectivity of radical chemistry, the construction of C—Si bond via free radical silylation reaction has achieved great progress in recent years. The research progress of the radical silylation reactions exploring silane as the precursor of silicon radical in the last decade is summarized, and the related reaction mechanism is discussed.
Xihui Yang , Haowei Gao , Jiale Yan , Lei Shi . Recent Progress in Radical-Mediated Si—H Functionalization of Silanes: An Effective Strategy for the Synthesis of Organosilanes Containing C—Si Bond[J]. Chinese Journal of Organic Chemistry, 2022 , 42(12) : 4122 -4151 . DOI: 10.6023/cjoc202207047
| [1] | Du, X.; Huang, Z. ACS Catal. 2017, 7, 1227. |
| [2] | Ramesh, R.; Reddy, D. S. J. Med. Chem. 2018, 61, 3779. |
| [3] | (a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry, Wiley, New York, 2000. |
| [3] | (b) B?hr, S.; Xue, W.; Oestreich, M. ACS Catal. 2018, 9, 16-24. |
| [4] | Parsaee, F.; Senarathna, M. C.; Kannangara, P. B.; Alexander, S. N.; Arche, P. D. E.; Welin, E. R. Nat. Rev. Chem. 2021, 5, 486. |
| [5] | Lu, L.; Siu, J. C.; Lai, Y.; Lin, S. J. Am. Chem. Soc. 2020, 142, 21272. |
| [6] | (a) Vulovic, B.; Cinderella, A. P.; Watson, D. A. ACS Catal. 2017, 7, 8113. |
| [6] | (b) Lalonde, M.; Chan, T. H. Synthesis 1985, 817. |
| [7] | (a) Shang, X.; Liu, Z.-Q. Org. Biomol. Chem. 2016, 14, 7829. |
| [7] | (b) Zhang, X. P.; Fang, J. K.; Cai, C.; Lu, G. P. Chin. Chem. Lett. 2021, 32, 1280. |
| [7] | (c) Li, J.-S.; Wu, J. ChemPhotoChem 2018, 2, 839. |
| [7] | (d) Chatgilialoglu, C.; Ferreri, C.; Landais, Y.; Timokhin, V. I. Chem. Rev. 2018, 118, 6516. |
| [8] | Zhang, L.; Hang, Z.; Liu, Z. Q. Angew. Chem., Int. Ed. 2016, 55, 236. |
| [9] | Gu, J.; Cai, C. Chem. Commun. 2016, 52, 10779. |
| [10] | Xu, R.; Cai, C. Catal. Commun. 2018, 107, 5. |
| [11] | Lin, Y. M.; Lu, G. P.; Wang, R. K.; Yi, W. B. Org. Lett. 2017, 19, 1100. |
| [12] | Zhang, X.; Liu, M.-X.; Wang, T.-L.; Wang, Y.-Q.; Wang, X.-C.; Quan, Z.-J. Org. Chem. Front. 2019, 6, 3365. |
| [13] | Chang, X. H.; Wang, Z. L.; Zhao, M.; Yang, C.; Li, J. J.; Ma, W. W.; Xu, Y. H. Org. Lett. 2020, 22, 1326. |
| [14] | Gan, Q. C.; Song, Z. Q.; Tung, C. H.; Wu, L. Z. Org. Lett. 2022, 24, 5192. |
| [15] | Zhang, L.; Liu, D.; Liu, Z. Q. Org. Lett. 2015, 17, 2534. |
| [16] | Yan, Z.; Xie, J.; Zhu, C. Adv. Synth. Catal. 2017, 359, 4153. |
| [17] | Peng, H.; Yu, J. T.; Jiang, Y.; Cheng, J. Org. Biomol. Chem. 2015, 13, 10299. |
| [18] | Gao, P.; Zhang, W.; Zhang, Z. Org. Lett. 2016, 18, 5820. |
| [19] | Wu, L.-J.; Tan, F.-L.; Li, M.; Song, R.-J.; Li, J.-H. Org. Chem. Front. 2017, 4, 350. |
| [20] | Zhang, H.; Wu, X.; Zhao, Q.; Zhu, C. Chem. Asian J. 2018, 13, 2453. |
| [21] | Yang, Y.; Song, R. J.; Ouyang, X. H.; Wang, C. Y.; Li, J. H.; Luo, S. Angew. Chem., Int. Ed. 2017, 56, 7916. |
| [22] | Lan, Y.; Chang, X.-H.; Fan, P.; Shan, C.-C.; Liu, Z.-B.; Loh, T.-P.; Xu, Y.-H. ACS Catal. 2017, 7, 7120. |
| [23] | Zhang, C.; Pi, J.; Wang, L.; Liu, P.; Sun, P. Org. Biomol. Chem., 2018, 16, 9223. |
| [24] | Nozawa-Kumada, K.; Ojima, T.; Inagi, M.; Shigeno, M.; Kondo, Y. Org. Lett. 2020, 22, 9591. |
| [25] | Chen, F.; Zheng, Y.; Yang, H.; Yang, Q. Y.; Wu, L. Y.; Zhou, N. Adv. Synth. Catal. 2022, 364, 1537. |
| [26] | Xue, Y.; Guo, Z.; Chen, X.; Li, J.; Zou, D.; Wu, Y.; Wu, Y. Org. Biomol. Chem. 2022, 20, 989. |
| [27] | Leifert, D.; Studer, A. Org. Lett. 2015, 17, 386. |
| [28] | Xu, Z.; Chai, L.; Liu, Z. Q. Org. Lett. 2017, 19, 5573. |
| [29] | Li, Y.; Shu, K.; Liu, P.; Sun, P. Org. Lett. 2020, 22, 6304. |
| [30] | Wang, L.; Zhu, H.; Guo, S.; Cheng, J.; Yu, J. T. Chem. Commun. 2014, 50, 10864. |
| [31] | Yang, Y.; Song, R. J.; Li, Y.; Ouyang, X. H.; Li, J. H.; He, D. L. Chem. Commun. 2018, 54, 1441. |
| [32] | Qrareya, H.; Dondi, D.; Ravelli, D.; Fagnoni, M. ChemCatChem 2015, 7, 3350. |
| [33] | Zhou, R.; Goh, Y. Y.; Liu, H.; Tao, H.; Li, L.; Wu, J. Angew. Chem., Int. Ed. 2017, 56, 16621. |
| [34] | Zhu, J.; Cui, W.-C.; Wang, S.; Yao, Z.-J. J. Org. Chem. 2018, 83, 14600. |
| [35] | Zhu, J.; Cui, W. C.; Wang, S.; Yao, Z. J. Org. Lett. 2018, 20, 3174. |
| [36] | Cai, Y.; Zhao, W.; Wang, S.; Liang, Y.; Yao, Z. J. Org. Lett. 2019, 21, 9836. |
| [37] | Liang, H.; Ji, Y. X.; Wang, R. H.; Zhang, Z. H.; Zhang, B. Org. Lett. 2019, 21, 2750. |
| [38] | Hou, J.; Ee, A.; Cao, H.; Ong, H. W.; Xu, J. H.; Wu, J. Angew. Chem., Int. Ed. 2018, 57, 17220. |
| [39] | Zhang, Z.; Hu, X. ACS Catal. 2019, 10, 777. |
| [40] | Cui, W. C.; Zhao, W.; Gao, M.; Liu, W.; Wang, S.; Liang, Y.; Yao, Z. J. Chem.-Eur. J. 2019, 25, 16506. |
| [41] | Hou, H.; Xu, Y.; Yang, H.; Chen, X.; Yan, C.; Shi, Y.; Zhu, S. Org. Lett. 2020, 22, 1748. |
| [42] | Neogi, S.; Kumar Ghosh, A.; Mandal, S.; Ghosh, D.; Ghosh, S.; Hajra, A. Org. Lett. 2021, 23, 6510. |
| [43] | Ke, J.; Liu, W.; Zhu, X.; Tan, X.; He, C. Angew. Chem., Int. Ed. 2021, 60, 8744. |
| [44] | Yang, C.; Wang, J.; Li, J.; Ma, W.; An, K.; He, W.; Jiang, C. Adv. Synth. Catal. 2018, 360, 3049. |
| [45] | Liu, S.; Pan, P.; Fan, H.; Li, H.; Wang, W.; Zhang, Y. Chem. Sci. 2019, 10, 3817. |
| [46] | Rammal, F.; Gao, D.; Boujnah, S.; Hussein, A. A.; Lalevée, J.; Gaumont, A.-C.; Morlet-Savary, F.; Lakhdar, S. ACS Catal. 2020, 10, 13710. |
| [47] | Dai, C.; Zhan, Y.; Liu, P.; Sun, P. Green Chem. 2021, 23, 314. |
| [48] | Zhang, W.; Lu, Q.; Wang, M.; Zhang, Y.; Xia, X. F.; Wang, D. Org. Lett. 2022, 24, 3797. |
| [49] | Yu, W. L.; Luo, Y. C.; Yan, L.; Liu, D.; Wang, Z. Y.; Xu, P. F. Angew. Chem., Int. Ed. 2019, 58, 10941 |
| [50] | Inoue, M.; Sumii, Y.; Shibata, N. ACS Omega 2020, 5, 10633. |
| [51] | Yue, F.; Liu, J.; Ma, H.; Liu, Y.; Dong, J.; Wang, Q. Org. Lett. 2022, 24, 4019. |
| [52] | Luo, C.; Zhou, Y.; Chen, H.; Wang, T.; Zhang, Z. B.; Han, P.; Jing, L. H. Org. Lett. 2022, 24, 4286. |
| [53] | Luo, C.; Lu, W. H.; Wang, G. Q.; Zhang, Z. B.; Li, H. Q.; Han, P.; Yang, D.; Jing, L. H.; Wang, C. J. Org. Chem. 2022, 87, 3567. |
| [54] | Romain, E.; Fopp, C.; Chemla, F.; Ferreira, F.; Jackowski, O.; Oestreich, M.; Perez-Luna, A. Angew. Chem., Int. Ed. 2014, 53, 11333. |
| [55] | Toutov, A. A.; Liu, W. B.; Betz, K. N.; Fedorov, A.; Stoltz, B. M.; Grubbs, R. H. Nature 2015, 518, 80. |
| [56] | Liu, W. B.; Schuman, D. P.; Yang, Y. F.; Toutov, A. A.; Liang, Y.; Klare, H. F. T.; Nesnas, N.; Oestreich, M.; Blackmond, D. G.; Virgil, S. C.; Banerjee, S.; Zare, R. N.; Grubbs, R. H.; Houk, K. N.; Stoltz, B. M. J. Am. Chem. Soc. 2017, 139, 6867. |
| [57] | Dong, J.; Yuan, X. A.; Yan, Z.; Mu, L.; Ma, J.; Zhu, C.; Xie, J. Nat. Chem. 2021, 13, 182. |
| [58] | Walsh, R. Acc. Chem. Res. 1981, 14, 246. |
/
| 〈 |
|
〉 |
