综述与进展

自由基介导的硅烷Si—H键官能团化研究进展: 一种合成含C—Si键有机硅化合物的有效策略

  • 杨惜晖 ,
  • 高皓炜 ,
  • 闫甲乐 ,
  • 史雷
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  • a 哈尔滨工业大学(深圳) 广东深圳 518055
    b 广东省催化化学重点实验室 广东深圳 518055
共同第一作者

收稿日期: 2022-07-31

  修回日期: 2022-08-28

  网络出版日期: 2022-09-23

基金资助

国家自然科学基金(21871067); 国家自然科学基金(22271069); 广东省自然科学基金(2021A1515010190); 元素有机化学国家重点实验室(202009); 广东省催化化学重点实验室(2020B121201002); 中央高校基本科研业务费专项资金(HIT.OCEF.2021035)

Recent Progress in Radical-Mediated Si—H Functionalization of Silanes: An Effective Strategy for the Synthesis of Organosilanes Containing C—Si Bond

  • Xihui Yang ,
  • Haowei Gao ,
  • Jiale Yan ,
  • Lei Shi
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  • a Harbin Institute of Technology (Shenzhen), Shenzhen, Guangdong 518055
    b Guangdong Provincial Key Laboratory of Catalysis, Shenzhen, Guangdong 518055
These authors contributed equally to this work.

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)

摘要

有机硅化合物由于具有独特的物理、化学和生理性质, 已经成为材料化学、药物化学及合成化学等领域中用途广泛的中间体和产品. 在过去一个世纪的发展中, 含C—Si键的有机硅化合物的合成逐渐成为科研人员的研究热点. 由于自由基化学的官能团容忍度较高、原子经济性及化学选择性较好, 近年来利用自由基硅基化反应构建C—Si键的方法取得了重要进展. 详细总结了近十年以硅烷为硅基自由基前体的自由基硅基化反应的研究进展并阐述相关反应机理.

本文引用格式

杨惜晖 , 高皓炜 , 闫甲乐 , 史雷 . 自由基介导的硅烷Si—H键官能团化研究进展: 一种合成含C—Si键有机硅化合物的有效策略[J]. 有机化学, 2022 , 42(12) : 4122 -4151 . DOI: 10.6023/cjoc202207047

Abstract

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.

参考文献

[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.
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