Citation: Zhang Jing, Chen Yiyun. Visible-Light-Induced Carboxyl and Alkoxyl Radical Generations and Reactions[J]. Acta Chimica Sinica, ;2017, 75(1): 41-48. doi: 10.6023/A16080416 shu

Visible-Light-Induced Carboxyl and Alkoxyl Radical Generations and Reactions

Zhang Jing ,
Chen Yiyun ^*,,

State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Chen Yiyun, yiyunchen@sioc.ac.cn
Received Date: 15 August 2016

Fund Project: the National Basic Research Program of China 2014CB910304National Natural Science Foundation of China 21272260the Strategic Priority Research Program of the Chinese Academy of Sciences XDB20020200National Natural Science Foundation of China 21472230

Figures(13)

The carboxyl and alkoxyl radicals generated from visible light photoredox reactions are important reaction intermediates in organic synthesis, which have witnessed conceivable progress recently. In this review, we focus on visible-light-induced photoredox methods to generate carboxyl radicals from carboxylate derivatives and carboxylates, as well as alkoxyl radicals from alcohol derivatives and alcohols, and briefly discuss their synthetic applications.
- visible light,
- radical reaction,
- carboxyl radical,
- alkoxyl radical
1. [1]
  Gooßen, L. J.; Rodríguez, N.; Gooßen, K. Angew. Chem., Int. Ed. 2008, 47, 3100. doi: 10.1002/(ISSN)1521-3773
2. [2]
  Xuan, J.; Zhang, Z. G.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 15632. doi: 10.1002/anie.201505731
3. [3]
  Huang, H.; Jia, K.; Chen, Y. ACS Catal. 2016, 6, 4983. doi: 10.1021/acscatal.6b01379
4. [4]
  Guan, B.; Xu, X.; Wang, H.; Li, X. Chin. J. Org. Chem. 2016, 36, 1564 (in Chinese). doi: 10.6023/cjoc201601012
5. [5]
  Čeković, Ž. Tetrahedron 2003, 59, 8073. doi: 10.1016/S0040-4020(03)01202-X
6. [6]
  Boto, A.; Hernandez, D.; Hernandez, R.; Suárez, E. J. Org. Chem. 2003, 68, 5310. doi: 10.1021/jo034442f
7. [7]
  Salamone, M.; Bietti, M. Acc. Chem. Res. 2015, 48, 2895. doi: 10.1021/acs.accounts.5b00348
8. [8]
  Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. doi: 10.1021/cr300503r
9. [9]
  Schultz, D. M.; Yoon, T. P. Science2014, 343, 985.
10. [10]
  Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102. doi: 10.1039/B913880N
11. [11]
  Xuan, J.; Xiao, W. J. Angew. Chem., Int. Ed. 2012, 51, 6828. doi: 10.1002/anie.201200223
12. [12]
  Hu, C. C.; Chen, Y. Y. Tetrahedron Lett. 2015, 56, 884. doi: 10.1016/j.tetlet.2014.12.034
13. [13]
  Okada, K.; Okamoto, K.; Morita, N.; Okubo, K.; Oda, M. J. Am. Chem. Soc. 1991, 113, 9401. doi: 10.1021/ja00024a074
14. [14]
  Schnermann, M. J.; Overman, L. E. Angew. Chem., Int. Ed. 2012, 51, 9576. doi: 10.1002/anie.v51.38
15. [15]
  Yang, J.; Zhang, J.; Qi, L.; Hu, C. C.; Chen, Y. Y. Chem. Commun. 2015, 51, 5275. doi: 10.1039/C4CC06344A
16. [16]
  Hu, C. C.; Chen, Y. Y. Org. Chem. Front. 2015, 2, 1352. doi: 10.1039/C5QO00187K
17. [17]
  Xie, J.; Xu, P.; Li, H. M.; Xue, Q. C.; Jin, H. M.; Cheng, Y. X.; Zhu, C. J. Chem. Commun. 2013, 49, 5672. doi: 10.1039/c3cc42672f
18. [18]
  He, Z.; Bae, M.; Wu, J.; Jamison, T. F. Angew. Chem., Int. Ed. 2014, 53, 14451. doi: 10.1002/anie.201408522
19. [19]
  Kachkovskyi, G.; Faderl, C.; Reiser, O. Adv. Synth. Catal. 2013, 355, 2240. doi: 10.1002/adsc.201300221
20. [20]
  Zuo, Z. W.; MacMillan, D. W. C. J. Am. Chem. Soc. 2014, 136, 5257. doi: 10.1021/ja501621q
21. [21]
  Ventre, S.; Petronijevic, F. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 5654. doi: 10.1021/jacs.5b02244
22. [22]
  Liu, J.; Liu, Q.; Yi, H.; Qin, C.; Bai, R. P.; Qi, X. T.; Lan, Y.; Lei, A. W. Angew. Chem., Int. Ed. 2014, 53, 502. doi: 10.1002/anie.v53.2
23. [23]
  Chu, L. L.; Lipshultz, J. M.; MacMillan, D. W. C. Angew. Chem., Int. Ed. 2015, 54, 7929. doi: 10.1002/anie.201501908
24. [24]
  Wang, G. Z.; Shang, R.; Cheng, W. M.; Fu, Y. Org. Lett. 2015, 17, 4830. doi: 10.1021/acs.orglett.5b02392
25. [25]
  Zhou, Q. Q.; Guo, W.; Ding, W.; Wu, X.; Chen, X.; Lu, L. Q.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 11196. doi: 10.1002/anie.201504559
26. [26]
  Le Vaillant, F.; Courant, T.; Waser, J. Angew. Chem., Int. Ed. 2015, 54, 11200. doi: 10.1002/anie.201505111
27. [27]
  Wu, X. X.; Meng, C. N.; Yuan, X. Q.; Jia, X. T.; Qian, X. H.; Ye, J. X. Chem. Commun. 2015, 51, 11864. doi: 10.1039/C5CC04527D
28. [28]
  Luo, J.; Zhang, J. ACS Catal.2016, 6, 873. doi: 10.1021/acscatal.5b02204
29. [29]
  Huang, H. C.; Zhang, G. J.; Chen, Y. Y. Angew. Chem., Int. Ed. 2015, 54, 7872. doi: 10.1002/anie.201502369
30. [30]
  Tan, H.; Li, H. J.; Ji, W. Q.; Wang, L. Angew. Chem. Int. Ed. 2015, 54, 8374. doi: 10.1002/anie.201503479
31. [31]
  Zhang, J.; Li, Y.; Zhang, F. Y.; Hu, C. C.; Chen, Y. Y. Angew. Chem., Int. Ed. 2016, 55, 1872. doi: 10.1002/anie.201510014
32. [32]
  Wang, C. Y.; Harms, K.; Meggers, E. Angew. Chem., Int. Ed. 2016, 55, 13495. doi: 10.1002/anie.v55.43
33. [33]
  Jia, K. F.; Zhang, F. Y.; Huang, H. C.; Chen, Y. Y. J. Am. Chem. Soc. 2016, 138, 1514. doi: 10.1021/jacs.5b13066
34. [34]
  Yayla, H. G.; Wang, H. J.; Tarantino, K. T.; Orbe, H. S.; Knowles, R. R. J. Am. Chem. Soc. 2016, 138, 10794. doi: 10.1021/jacs.6b06517
35. [35]
  Guo, J. J.; Hu, A. H.; Chen, Y. L.; Sun, J. F.; Tang, H. M.; Zuo, Z. W. Angew. Chem., Int. Ed. 2016, 55, 15319. doi: 10.1002/anie.v55.49
36. [36]
  Hu, X. Q.; Chen, J.; Chen, J. R.; Yan, D. M.; Xiao, W. J. Chem. Eur. J. 2016, 22, 14141. doi: 10.1002/chem.v22.40
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