Citation: Song Changhua, Shen Xu, Yu Fang, He Yupeng, Yu Shouyun. Generation and Application of Iminyl Radicals from Oxime Derivatives Enabled by Visible Light Photoredox Catalysis[J]. Chinese Journal of Organic Chemistry, ;2020, 40(11): 3748-3759. doi: 10.6023/cjoc202004008 shu

Generation and Application of Iminyl Radicals from Oxime Derivatives Enabled by Visible Light Photoredox Catalysis

Song Changhua ^a,b ,
Shen Xu ^b ,
Yu Fang ^a ,
He Yupeng ^a,, ,
Yu Shouyun ^b,,

a.
College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Fushun, Liaoning 113001
b.
State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023

Corresponding author: He Yupeng, yupeng.he@lnpu.edu.cn Yu Shouyun, yushouyun@nju.edu.cn
Received Date: 6 April 2020
Revised Date: 29 April 2020
Available Online: 7 May 2020
Fund Project: the National Natural Science Foundation of China 21732003the National Natural Science Foundation of China 21978124Project supported by the National Natural Science Foundation of China (Nos. 21732003, 21978124) and the Innovative Talent Project of Educational Department of Liaoning Province (No. LR2018019)the Innovative Talent Project of Educational Department of Liaoning Province LR2018019

Figures(22)

The advent of visible light photoredox catalysis has transformed the way of single-electron transfer (SET) processes and accessing radical species. As a result, the chemistry of nitrogen-centered radicals has witnessed a remarkable gain in interest. Specifically, under visible light photoredox catalysis, iminyl radicals can be generated from oxime derivatives, such as O-acyl oximes, O-aryl oximes and α-imino-oxy acids. Meanwhile, the reactivity of iminyl radcials is investigated systematically. Iminyl radicals can undergo four major classes of reactions, namely addition to arenes, intramolecular hydrogen atom transfer and subsequent reactions, addition to alkenes, Norrish type-I fragmentation (cleavage of α-carbon-carbon bonds) and subsequent reactions. In this review, the most significant progresses in the use of oximes and their derivatives as iminyl precursors are discussed and their engagement in photoredox-mediated transformations is outlined.
- nitrogen-centered radical,
- iminyl radical,
- photoredox catalysis,
- visible light
1. [1]
  Lawrence, S. A. Amines: Synthesis Properties and Applications, Cambridge University, Cambridge, 2005, p. 1016.
2. [2]
  Zard, S. Z. Chem. Soc. Rev. 2008, 37, 1603. doi: 10.1039/b613443m
3. [3]
4. [4]
5. [5]
  Walton, J. C. Acc. Chem. Res. 2014, 47, 1406. doi: 10.1021/ar500017f
6. [6]
  Luo, Y.-R. Handbook of Bond Dissociation Energies in Organic Compounds, CRC, Boca Raton, 2003, p. 392.
7. [7]
  Jiang, H.; An, X. D.; Tong, K.; Zheng, T.; Zhang, Y.; Yu, S. Angew. Chem., Int. Ed. 2015, 54, 4055. doi: 10.1002/anie.201411342
8. [8]
  An, X.-D.; Yu, S. Org. Lett. 2015, 17, 2692. doi: 10.1021/acs.orglett.5b01096
9. [9]
  Sun, J.-J; He, Y.-Y; An, X.-D; Zhang, X; Yu, L; Yu, S. Org. Chem. Front. 2018, 5, 977. doi: 10.1039/C7QO00992E
10. [10]
  Liu, X.-B.; Qing, Z.-X.; Zheng, X.-Y.; Zeng, J.-G.; Cheng, P.; Xie, H.-Q. Molecules 2016, 21, 1690. doi: 10.3390/molecules21121690
11. [11]
  Matsushita, Y.; Ochi, R. Tanaka, Y.; Koike, T.; Akita, M. Org. Chem. Front. 2020, 7, 1243. doi: 10.1039/D0QO00271B
12. [12]
  (a) Qin, Q.-X; Yu, S. Org. Lett. 2015, 17, 1894.
  (b) Shen, X.; Zhao, J.-J.; Yu, S. Org. Lett. 2018, 20, 5523.
13. [13]
  Shu, W.; Nevado, C. Angew. Chem., Int. Ed. 2017, 56, 1881. doi: 10.1002/anie.201609885
14. [14]
  Ma, Z.-Y.; Guo, L.-N.; Gu, Y.-R.; Chen, L.; Duan, X.-H. Adv. Synth. Catal. 2018, 360, 4341. doi: 10.1002/adsc.201801198
15. [15]
  Chen, L; Guo, L.-N.; Ma, Z.-Y.; Gu, Y.-R.; Zhang, J.; Duan, X.-H. J. Org. Chem. 2019, 84, 6475. doi: 10.1021/acs.joc.9b00525
16. [16]
  Dauncey, E. M.; Morcillo, S. P.; Douglas, J. J.; Sheikh, N. S.; Leonori, D. Angew. Chem., Int. Ed. 2018, 57, 744. doi: 10.1002/anie.201710790
17. [17]
  Jiang, H.; Studer, A. Angew. Chem., Int. Ed. 2018, 57, 1692. doi: 10.1002/anie.201712066
18. [18]
  Li, J.-J.; Zhang, P.-P.; Jiang, M.; Yang, H.-J.; Zhao, Y.-F.; Fu, H. Org. Lett. 2017, 19, 1994. doi: 10.1021/acs.orglett.7b00533
19. [19]
  Li, Y.-W.; Mao, R.-Y.; Wu, J. Org. Lett. 2017, 19, 4472. doi: 10.1021/acs.orglett.7b02010
20. [20]
  Tadic-Biadatti, M.-H. L.; Callier-Dublanchet, A.; Horner, J. H.; Quiclet-Sire, B.; Zard, S. Z.; Newcomb, M. J. Org. Chem. 1997, 62, 559. doi: 10.1021/jo961530+
21. [21]
  Boivin, J; Schiano, A.-M; Zard, S. Z; Zhang, H.-W. Tetrahedron Lett. 1999, 40, 4531. doi: 10.1016/S0040-4039(99)00720-0
22. [22]
  Mikami, T.; Narasaka, K. Chem. Lett. 1999, 24, 338.
23. [23]
  Davies, J.; Booth, S. G.; Essafi, S.; Dryfe, Robert A. W.; Leonori, D. Angew. Chem., Int. Ed. 2015, 54, 14017. doi: 10.1002/anie.201507641
24. [24]
  Cai, S.-H.; Xie, J.-H; Song, S.-J.; Ye, L.; Feng, C.; Loh, T. P. ACS Catal. 2016, 6, 5571. doi: 10.1021/acscatal.6b01230
25. [25]
  Jiang, H.; Studer, A. Angew. Chem., Int. Ed. 2017, 56, 12273. doi: 10.1002/anie.201706270
26. [26]
  Davies, J.; Sheikh, N. S.; Leonori, D. Angew. Chem., Int. Ed. 2017, 56, 13361. doi: 10.1002/anie.201708497
27. [27]
  (a) Yin, W.; Wang, X. New J. Chem. 2019, 43, 3254.
  (b) Xiao, T.-B.; Huang, H.-T.; Anand, D.; Zhou, L. Synthesis 2020, Synthesis 2020, 52, 1585.
28. [28]
  Boivin, J.; Fouquet, E.; Zard, S. Z. Tetrahedron 1994, 50, 1757. doi: 10.1016/S0040-4020(01)80850-4
29. [29]
  Yu, X.-Y.; Chen, J.-R.; Wang, P.-Z.; Yang, M.-N.; Liang, D.; Xiao, W.-J. Angew. Chem., Int. Ed. 2018, 57, 738. doi: 10.1002/anie.201710618
30. [30]
  He, B.-Q.; Yu, X.-Y.; Wang, P.-Z.; Chen, J.-R.; Xiao, W.-J. Chem. Commun. 2018, 54, 12262. doi: 10.1039/C8CC07072E
31. [31]
  Wang, P.-Z.; Yu, X.-Y.; Li, C.-Y.; He, B.-Q.; Chen, J.-R.; Xiao, W.-J. Chem. Commun. 2018, 54, 9925. doi: 10.1039/C8CC06145A
32. [32]
  Li, L.; Chen, H.; Mei, M.; Zhou, L. Chem. Commun. 2017, 53, 11544. doi: 10.1039/C7CC07347J
33. [33]
  Vaillant, F. L.; Garreau, M.; Nicolai, S.; Grynova, G.; Corminboeuf, C.; Waster, J. Chem. Sci. 2018, 9, 5883. doi: 10.1039/C8SC01818A
34. [34]
  Zhang, J.; Li, X.-F.; Xie, W.-L.; Ye, S.-Q.; Wu, J. Org. Lett. 2019, 21, 4950. doi: 10.1021/acs.orglett.9b01323
35. [35]
  Zheng, M.; Li, G.-L.; Lu, H.-J. Org. Lett. 2019, 21, 1216. doi: 10.1021/acs.orglett.9b00201
36. [36]
  Liu, Y.; Wang, Q.-L.; Chen, Z.; Li, H.; Xiong, B.-Q.; Zhang, P.-L.; Tang, K.-W. Chem. Commun. 2020, 56, 3011. doi: 10.1039/C9CC10057A
37. [37]
  Jian, Y.; Chen, M.; Yang, Chao; Xia, W.-J. Eur. J. Org. Chem. 2020, 1439.
38. [38]
  Wang, P.-Z.; He, B.-Q.; Cheng, Y.; Chen, J.-R.; Xiao, W.-J. Org. Lett. 2019, 21, 6924. doi: 10.1021/acs.orglett.9b02535
39. [39]
  Yu, X.-Y.; Zhao, Q.-Q.; Chen, J.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2018, 57, 15505. doi: 10.1002/anie.201809820
40. [40]
  Chen, J.; He, B-Q.; Wang, P.-Z.; Yu, X.-Y.; Zhao, Q.-Q.; Chen, J.-R.; Xiao, W.-J. Org. Lett. 2019, 21, 4359. doi: 10.1021/acs.orglett.9b01529
41. [41]
  Lu, B.; Cheng, Y.; Chen, L.-Y.; Chen, J. R.; Xiao, W.-J. ACS Catal. 2019, 9, 8159. doi: 10.1021/acscatal.9b02830
42. [42]
  Yu, X.-Y.; Chen, J.; Chen, H.-W.; Xiao, W.-J.; Chen, J.-R. Org. Lett. 2020, 22, 2333. doi: 10.1021/acs.orglett.0c00532
43. [43]
  Dauncey, E. M.; Dighe, S. U.; Douglas, J. J.; Leonori, D. Chem. Sci. 2019, 10, 7728. doi: 10.1039/C9SC02616A
44. [44]
  Chen, J.; Wang, P.-Z.; Lu, B.; Liang, D.; Yu, X.-Y.; Xiao, W.-J.; Chen, J. R. Org. Lett. 2019, 21, 9763. doi: 10.1021/acs.orglett.9b03970
45. [45]
  Wang, T.; Wang; Y.-N.; Wang, R.; Zhang, B.-C.; Yang, C.; Li, Y.-L.; Wang, X.-S. Nat. Commun. 2019, 10, 5373. doi: 10.1038/s41467-019-13369-x
46. [46]
  (a) Li, Y.-H.; Wang, C.-H.; Gao, S.-Q.; Qi, F.-M.; Yang, S.-D. Chem. Commun. 2019, 55, 11888.
  (b) Li, C.; Qi, Z.-C.; Yang, Q.; Qiang, X.-Y.; Yang, A.-D. Chin. J. Chem. 2018, 36, 1052.
47. [47]
  (a) Cheng, Y.-Y.; Lei, T.; Su, L.-L.; Fan, X.-W.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Org. Lett. 2019, 21, 8789.
  (b) Fan, X.-W.; Lei, T.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Org. Lett. 2019, 21, 4153.
  (c) Fan, X.-W.; Lei, T.; Liu, Z.; Yang, X.-L.; Cheng, Y.-Y.; Liang, G.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Eur. J. Org. Chem. 2020, 10, 1551.
48. [48]
  Qin, Q.; Han, Y.-Y; Jiao, Y.-Y; He, Y.; Yu, S. Org. Lett. 2017, 19, 2909. doi: 10.1021/acs.orglett.7b01145
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