Citation: Chen Yilin, Chang Liang, Zuo Zhiwei. Visible Light Photoredox-Induced Smiles Rearrangement[J]. Acta Chimica Sinica, ;2019, 77(9): 794-802. doi: 10.6023/A19050179 shu

Visible Light Photoredox-Induced Smiles Rearrangement

Shanghaitech University, School of Physical Science and Technology, Shanghai 201210

Corresponding author: Zuo Zhiwei, zuozhw@shanghaitech.edu.cn
Received Date: 14 May 2019
Available Online: 4 September 2019
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21772121) and the "Thousand Plan" Youth programthe National Natural Science Foundation of China 21772121

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The intramolecular aromatic ring systems migration reactions, namely Smiles rearrangement is a powerful method for (hetero)aryl group functionalization. It can be employed as a complementary strategy to arene functionalization, and has found its broad applications in synthetic chemistry. After the initial documentation in 1894 this chemistry was intensively investigated by Smiles. In its classical pathway, the migration of aromatic ring system takes place ipso nucleophilic substitution. Accordingly, the migrating (hetero)aryl groups are highly electronic and steric-dependent. Moreover, as new reaction modes reported, advances have been made in the areas for arene C-C, C-N and C-O bond formation and radical triggered Smiles rearrangement has also enriched migrating units. Recently, there has been a rapid growth in the transformation induced by visible-light photocatalysis. Harnessing visible light as the energy source for chemical reactions usually serves as an environmentally benign alternative in comparison with classical radical pathway. Furthermore, photoredox-induced rearrangement represents a valuable and efficient approach for facilitating both the radical-based bond-cleaving and bond-forming events in a single step. It has become an effective tool for both synthesis and late stage modification of bio-active molecules. The last five years has witnessed many important advances in exploring photo-induced Smiles reactions, which make this classic reaction regained its attention. Significant progress has been made for expediting the generation of N-centered, C-centered and O-centered from a variety of precursors before single electron transfer rearrangement. This powerful synthetic platform for efficient promotes (hetero) aromatic group construction under mild reaction conditions, and has become a useful method for the synthesis and late stage functionalization of pharmaceutically interest products. In this perspective, we focus on visible light induced Smiles chemistry, which the major breakthroughs are classified based on migrating-induced radical species, and their synthetic applications are discussed briefly.
- visible-light photocatalysis,
- Smiles rearrangement,
- radical rearrangement
1. [1]
2. [2]
  (a) Warren, L. A.; Smiles, S. J. Chem. Soc. 1930, 1327; (b) Warren, L. A.; Smiles, S. J. Chem. Soc. 1930, 956; (c) Levi, A.; Warren, L. A.; Smiles, S. J. Chem. Soc. 1933, 1490.
3. [3]
  (a) Kong, W.; Merino, E.; Nevado, C. Angew. Chem., Int. Ed. 2014, 53, 5078; (b) Thaharn, W.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pohmakotr, M. Angew. Chem., Int. Ed. 2014, 53, 2212; (c) Fuentes, N.; Kong, W.; Fernández-Sánchez, L.; Merino, E.; Nevado, C. J. Am. Chem. Soc. 2015, 137, 964; (d) Wu, X.; Zhu, C. Chin. J. Chem. 2019, 37, 171.
4. [4]
  Douglas, J. J.; Albright, H.; Sevrin, M. J.; Cole, K. P.; Stephenson, C. R. J. Angew. Chem., Int. Ed. 2015, 54, 14898. doi: 10.1002/anie.201507369
5. [5]
  Benito Collado, A. B.; Diaz Buezo, N.; Jimenez-Aguado, A. M.; Lafuente Blanco, C.; Martinez-Grau, M. A.; Pedregal-Tercero, C.; Toledo Escribano, M. A. U.S. 8232289 B2, 2011.
6. [6]
  Douglas, J. J.; Sevrin, M. J.; Cole, K. P.; Stephenson, C. R. J. Org. Process Res. Dev. 2016, 20, 1148. doi: 10.1021/acs.oprd.6b00126
7. [7]
  Li, Y.; Hu, B.; Dong, W.; Xie, X.; Wan, J.; Zhang, Z. J. Org. Chem. 2016, 81, 7036. doi: 10.1021/acs.joc.6b00735
8. [8]
  Alpers, D.; Cole, K. P.; Stephenson, C. R. J. Angew. Chem., Int. Ed. 2018, 57, 12167. doi: 10.1002/anie.201806659
9. [9]
  Faderl, C.; Budde, S.; Kachkovskyi, G.; Rackl, D.; Reiser, O. J. Org. Chem. 2018, 83, 12192. doi: 10.1021/acs.joc.8b01538
10. [10]
  Liu, C.; Zhang, B. RSC Adv. 2015, 5, 61199. doi: 10.1039/C5RA08996D
11. [11]
  Brachet, E.; Marzo, L.; Selkti, M.; König, B.; Belmont, P. Chem. Sci. 2016, 7, 5002. doi: 10.1039/C6SC01095D
12. [12]
  Tang, S.; Yuan, L.; Deng, Y.-L.; Li, Z.-Z.; Wang, L.-N.; Huang, G.-X.; Sheng, R.-L. Tetrahedron Lett. 2017, 58, 329. doi: 10.1016/j.tetlet.2016.12.027
13. [13]
  Huang, H.; Li, Y. J. Org. Chem. 2017, 82, 4449. doi: 10.1021/acs.joc.7b00350
14. [14]
  Monos, T. M.; McAtee, R. C.; Stephenson, C. R. J. Science 2018, 361, 1369.
15. [15]
  Zard, S. Z. Chem. Soc. Rev. 2008, 37, 1603. doi: 10.1039/b613443m
16. [16]
  Yu, J.; Wu, Z.; Zhu, C. Angew. Chem., Int. Ed. 2018, 57, 17156. doi: 10.1002/anie.201811346
17. [17]
  Whalley, D. M.; Duong, H. A.; Greaney, M. F. Chem. Eur. J. 2019, 25, 1927. doi: 10.1002/chem.201805712
18. [18]
  Xu, P.; Hu, K.; Gu, Z.; Cheng, Y.; Zhu, C. Chem. Commun. 2015, 51, 7222. doi: 10.1039/C5CC01189B
19. [19]
  (a) Huang, H.-L.; Yan, H.; Yang, C.; Xia, W. Chem. Commun. 2015, 51, 4910; (b) Li, Y.; Liu, B.; Ouyang, X.-H.; Song, R.-J.; Li, J.-H. Org. Chem. Front. 2015, 2, 1457; (c) Cai, S.; Tian, Y.; Zhang, J.; Liu, Z.; Lu, M.; Weng, W.; Huang, M. Adv. Synth. Catal. 2018, 360, 4084; (d) Lu, M.; Qin, H.; Lin, Z.; Huang, M.; Weng, W.; Cai, S. Org. Lett. 2018, 20, 7611; (e) Wang, H.; Xu, Q.; Yu, S. Org. Chem. Front. 2018, 5, 2224; (f) Wang, Q.-L.; Chen, Z.; Zhou, C.-S.; Xiong, B.-Q.; Zhang, P.-L.; Yang, C.-A.; Liu, Y.; Zhou, Q. Tetrahedron Lett. 2018, 59, 4551; (g) Yin, Y.; Weng, W.-Z.; Sun, J.-G.; Zhang, B. Org. Biomol. Chem. 2018, 16, 2356; (h) Wei, X.-J.; Noël, T. J. Org. Chem. 2018, 83, 11377.
20. [20]
  Gu, L.; Gao, Y.; Ai, X.; Jin, C.; He, Y.; Li, G.; Yuan, M. Chem. Commun. 2017, 53, 12946. doi: 10.1039/C7CC06484E
21. [21]
  Zhou, N.-N.; Xu, P.; Li, W.-P.; Cheng, Y.-X.; Zhu, C.-J. Acta Chim. Sinica 2017, 75, 60.
22. [22]
  Yu, J.; Wang, D.; Xu, Y.; Wu, Z.; Zhu, C. Adv. Synth. Catal. 2018, 360, 744. doi: 10.1002/adsc.201701229
23. [23]
  Tang, N.; Yang, S.; Wu, X.; Zhu, C. Tetrahedron 2019, 75, 1639. doi: 10.1016/j.tet.2018.12.003
24. [24]
  Wu, X.; Wang, M.; Huan, L.; Wang, D.; Wang, J.; Zhu, C. Angew. Chem. 2018, 130, 1656. doi: 10.1002/ange.201709025
25. [25]
  Dondoni, A.; Marra, A. Chem. Rev. 2004, 104, 2557. doi: 10.1021/cr020079l
26. [26]
  Shu, W.; Genoux, A.; Li, Z.; Nevado, C. Angew. Chem., Int. Ed. 2017, 56, 10521. doi: 10.1002/anie.201704068
27. [27]
  Wang, N.; Gu, Q.-S.; Li, Z.-L.; Li, Z.; Guo, Y.-L.; Guo, Z.; Liu, X.-Y. Angew. Chem., Int. Ed. 2018, 57, 14225. doi: 10.1002/anie.201808890
28. [28]
  Wang, S.-F.; Cao, X.-P.; Li, Y. Angew. Chem., Int. Ed. 2017, 56, 13809. doi: 10.1002/anie.201706597
29. [29]
  Gonzalez-Gomez, J. C.; Ramirez, N. P.; Lana-Villarreal, T.; Bonete, P. Org. Biomol. Chem. 2017, 15, 9680. doi: 10.1039/C7OB02579C
30. [30]
  Li, J.; Liu, Z.; Wu, S.; Chen, Y. Org. Lett. 2019, 21, 2077. doi: 10.1021/acs.orglett.9b00353
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