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2023 , Vol. 43 >Issue 8: 2720 - 2742

DOI: https://doi.org/10.6023/cjoc202212017

综述与进展

可见光促进有机硅化合物参与的化学转化

  • 杨晓娜 ,
  • 郭宏宇 ,
  • 周荣
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  • 太原理工大学化学学院 山西太原 030024

收稿日期: 2022-12-13

  修回日期: 2023-02-23

  网络出版日期: 2023-04-14

基金资助

山西省自然科学基金(201901D111081); 山西省留学回国人员科研(2020-029)

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Progress in Visible-Light Promoted Transformations of Organosilicon Compounds

  • Xiaona Yang ,
  • Hongyu Guo ,
  • Rong Zhou
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  • College of Chemistry, Taiyuan University of Technology, Taiyuan, Shanxi 030024
*E-mail: ;

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)

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摘要

有机硅化合物具有重要用途, 被广泛应用于材料科学与药物化学等领域. 因此, 有机硅试剂参与的化学转化一直倍受关注. 近年来, 可见光催化迅速发展, 为有机合成化学提供了新的机遇. 在光氧化还原体系下, 有机硅试剂可以经由氢原子转移(Hydrogen atom transfer, HAT)或单电子转移(Single electron transfer, SET)过程转化为硅自由基或碳自由基进行反应, 具有条件温和、选择性好和原子经济性高等优势. 根据反应类型不同, 主要综述了有机硅试剂作为硅自由基前体参与的烯(炔)烃硅氢化反应、烯(炔)烃双官能化反应、氮杂芳烃的硅基化反应, 以及有机硅化合物作为碳自由基前体参与的亲核加成反应、Minisci反应、均裂取代反应和过渡金属介导的交叉偶联反应.

关键词： 有机硅化合物; 可见光催化; 氢原子转移(HAT); 单电子转移(SET); 硅自由基; 碳自由基

本文引用格式

杨晓娜 , 郭宏宇 , 周荣 . 可见光促进有机硅化合物参与的化学转化[J]. 有机化学, 2023 , 43(8) : 2720 -2742 . DOI: 10.6023/cjoc202212017

Abstract

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.

Key words： organosilicon compounds; visible light photocatalysis; hydrogen atom transfer (HAT); single electron transfer (SET); silyl radical; carbon radicals

参考文献

[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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