Citation: Ting Zou, Yishu He, Rui Liu, Yihao Zhang, Siping Wei, Ji Lu, Jun Wang, Lin Wang, Qiang Fu, Dong Yi. Photoredox-neutral ring-opening pyridylation of cyclic oximes via phosphoranyl radical-mediated NO/CC bond cleavages and sequential radical-radical coupling[J]. Chinese Chemical Letters, ;2023, 34(5): 107822. doi: 10.1016/j.cclet.2022.107822 shu

Photoredox-neutral ring-opening pyridylation of cyclic oximes via phosphoranyl radical-mediated NO/CC bond cleavages and sequential radical-radical coupling

Ting Zou ^{a, 1} ,
Yishu He ^{a, 1} ,
Rui Liu ^a ,
Yihao Zhang ^a ,
Siping Wei ^{a, c, *,} ,
Ji Lu ^a ,
Jun Wang ^a ,
Lin Wang ^a ,
Qiang Fu ^{a, **,} ,
Dong Yi ^{a, b, *,}

a.
Department of Medicinal Chemistry, School of Pharmacy, Southwest Medical University, Luzhou 646000, China
b.
Nuclear Medicine and Molecular Imaging Key Laboratory of Sichuan Province, Luzhou 646000, China
c.
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China

^**

swei1225@swmu.edu.cn

fuqiang@swmu.edu.cn

yidong@swmu.edu.cn

Received Date: 25 June 2022
Revised Date: 1 September 2022
Accepted Date: 13 September 2022
Available Online: 15 September 2022

Figures(7)

A novel photoredox-neutral ring-opening pyridylation of non-prefunctionalized cyclic oximes has been accomplished through phosphoranyl radical-mediated NO/CC bond cleavages followed by radical-radical coupling. This mild acid-, base-, and oxidant-free protocol provides highly site-selective and efficient access to distally pyridylated alkylnitriles, which could be scale-up synthesized and readily converted into skeletally diverse compounds. Notably, the oxidized ground-state photocatalyst generated via the SET oxidation of the highly reducing excited-state photocatalyst by cyanopyridines might initiate the following phosphoranyl radical-mediated deoxygenative process.
- Pyridylation,
- Cyclic oxime,
- Phosphoranyl radical,
- Photoredox-neutral,
- Radical-radical coupling
1. [1]
  T. Andou, Y. Saga, H. Komai, et al., Angew. Chem. Int. Ed. 52 (2013) 3213–3216. doi: 10.1002/anie.201208666
2. [2]
  Z. Deng, M. Zhao, F. Wang, et al., Nat. Commun. 11 (2020) 2569–2577. doi: 10.1038/s41467-020-16451-x
3. [3]
  M.A. Graham, S.A. Raw, D.M. Andrews, et al., Org. Process Res. Dev. 16 (2012) 1283–1292. doi: 10.1021/op300021m
4. [4]
  I. Mohammadzadeh, H. Sheibani, Chin. Chem. Lett. 23 (2012) 1327–1330. doi: 10.1016/j.cclet.2012.10.007
5. [5]
  I. Nakamura, Y. Oyama, D. Zhang, et al., Org. Chem. Front. 4 (2017) 1034–1036. doi: 10.1039/C6QO00703A
6. [6]
  Y. Nakao, Y. Yamada, N. Kashihara, et al., J. Am. Chem. Soc. 132 (2010) 13666–13668. doi: 10.1021/ja106514b
7. [7]
  J. Shen, Y. Zhang, Y. Yu, et al., Org. Chem. Front. 8 (2021) 901–907. doi: 10.1039/D0QO01218A
8. [8]
  P.F. Shi, Q. Jiang, Chin. Chem. Lett. 20 (2009) 168–170. doi: 10.1016/j.cclet.2008.10.029
9. [9]
  E. Vitaku, D.T. Smith, J.T. Njardarson, J. Med. Chem. 57 (2014) 10257–10274. doi: 10.1021/jm501100b
10. [10]
  X. Wei, L. Wang, W. Jia, et al., Chin. J. Chem. 32 (2014) 1245–1250. doi: 10.1002/cjoc.201400521
11. [11]
  G. Yang, W. Zhang, Chem. Soc. Rev. 47 (2018) 1783–1810. doi: 10.1039/C7CS00615B
12. [12]
  Z. Yin, L. Fan, C. Lin, et al., Chin. Chem. Lett. 33 (2022) 280–282. doi: 10.1016/j.cclet.2021.06.057
13. [13]
  B. Zhao, B. Prabagar, Z. Shi, Chem 7 (2021) 2585–2634. doi: 10.1016/j.chempr.2021.08.001
14. [14]
  Y.X. Jiang, L. Chen, C.K. Ran, et al., ChemSusChem 13 (2020) 6312–6317.
15. [15]
  L. Li, H. Chen, M. Mei, et al., Chem. Commun. 53 (2017) 11544–11547. doi: 10.1039/C7CC07347J
16. [16]
  Q. Liang, L. Lin, G. Li, et al., Chin. J. Chem. 39 (2021) 1948–1952. doi: 10.1002/cjoc.202100050
17. [17]
  Y. Liu, L. Wang, L.H. Zeng, et al., Chin. Chem. Lett. 33 (2022) 2383–2386. doi: 10.1016/j.cclet.2021.11.009
18. [18]
  X.Y. Yu, J. Chen, H.W. Chen, et al., Org. Lett. 22 (2020) 2333–2338. doi: 10.1021/acs.orglett.0c00532
19. [19]
  B. Zhao, C. Chen, J. Lv, et al., Org. Chem. Front. 5 (2018) 2719–2722. doi: 10.1039/C8QO00747K
20. [20]
  B. Zhao, H. Tan, C. Chen, et al., Chin. J. Chem. 36 (2018) 995–999. doi: 10.1002/cjoc.201800206
21. [21]
  B. Zhao, Y. Zheng, C. Chen, et al., Org. Chem. Front. 8 (2021) 2985–2989. doi: 10.1039/D1QO00182E
22. [22]
  L. Zhou, T. Xiao, H. Huang, et al., Synthesis 52 (2020) 1585–1601. doi: 10.1055/s-0039-1690844
23. [23]
  S.P. Morcillo, Angew. Chem. Int. Ed. 58 (2019) 14044–14054. doi: 10.1002/anie.201905218
24. [24]
  X. Zhu, Y. Huang, X. Xu, et al., Chin. Chem. Lett. 33 (2022) 817–820. doi: 10.1016/j.cclet.2021.07.030
25. [25]
  H.D. Zuo, S.S. Zhu, W.J. Hao, et al., ACS Catal. 11 (2021) 6010–6019. doi: 10.1021/acscatal.1c00842
26. [26]
  K. Kwon, R.T. Simons, M. Nandakumar, et al., Chem. Rev. 122 (2022) 2353–2428. doi: 10.1021/acs.chemrev.1c00444
27. [27]
  M. Wang, C. Chen, M. Ma, et al., J. Org. Chem. 87 (2022) 3577–3585. doi: 10.1021/acs.joc.1c03131
28. [28]
  P.Z. Wang, Y. Gao, J. Chen, et al., Nat. Commun. 12 (2021) 1815–1824. doi: 10.1038/s41467-021-22127-x
29. [29]
  Y.R. Gu, X.H. Duan, L. Yang, et al., Org. Lett. 19 (2017) 5908–5911. doi: 10.1021/acs.orglett.7b02902
30. [30]
  Y. Jian, M. Chen, C. Yang, et al., Eur. J. Org. Chem. 2020 (2020) 1439–1442. doi: 10.1002/ejoc.201900406
31. [31]
  X. Li, X. Yan, Z. Wang, et al., J. Org. Chem. 85 (2020) 2504–2511. doi: 10.1021/acs.joc.9b03204
32. [32]
  E.M. Dauncey, S.U. Dighe, J.J. Douglas, et al., Chem. Sci. 10 (2019) 7728–7733. doi: 10.1039/C9SC02616A
33. [33]
  A. Ghosh, M. Lecomte, S.H. Kim-Lee, et al., Angew. Chem. Int. Ed. 58 (2019) 2864–2869. doi: 10.1002/anie.201813919
34. [34]
  X.Q. Hu, Y.X. Hou, Z.K. Liu, et al., Org. Chem. Front. 7 (2020) 2319–2324. doi: 10.1039/D0QO00643B
35. [35]
  E.E. Stache, A.B. Ertel, R. Tomislav, et al., ACS Catal. 8 (2018) 11134–11139. doi: 10.1021/acscatal.8b03592
36. [36]
  P.J. Xia, Z.P. Ye, Y.Z. Hu, et al., Org. Lett. 21 (2019) 2658–2662. doi: 10.1021/acs.orglett.9b00651
37. [37]
  L. Zhang, X. Si, Y. Yang, et al., ACS Catal. 9 (2019) 6118–6123. doi: 10.1021/acscatal.9b01368
38. [38]
  M. Zhang, J. Xie, C. Zhu, Nat. Commun. 9 (2018) 3517–3526. doi: 10.1038/s41467-018-06019-1
39. [39]
  A.K. Clarke, A. Parkin, R.J.K. Taylor, et al., ACS Catal. 10 (2020) 5814–5820. doi: 10.1021/acscatal.0c00690
40. [40]
  J.I. Day, K. Teegardin, J. Weaver, et al., Org. Process Res. Dev. 20 (2016) 1156–1163. doi: 10.1021/acs.oprd.6b00101
41. [41]
  T.S. Teets, Y. Wu, D. Kim, Synlett 33 (2021) 1154–1179.
42. [42]
  B. Lipp, L.M. Kammer, M. Kucukdisli, et al., Chemistry 25 (2019) 8965–8969. doi: 10.1002/chem.201901175
43. [43]
  J.D. Cuthbertson, D.W. MacMillan, Nature 519 (2015) 74–77. doi: 10.1038/nature14255
44. [44]
  L. Gao, G. Wang, H. Chen, et al., Org. Chem. Front. 7 (2020) 2744–2751. doi: 10.1039/D0QO00827C
45. [45]
  T. Hoshikawa, M. Inoue, Chem. Sci. 4 (2013) 3118–3123. doi: 10.1039/c3sc51080h
46. [46]
  T. Wang, Y.N. Wang, R. Wang, et al., Nat. Commun. 10 (2019) 5373–5381. doi: 10.1038/s41467-019-13369-x
47. [47]
  F. Xiao, Y. Guo, Y.F. Zeng, Adv. Synth. Catal. 363 (2020) 120–143.
48. [48]
  W. Xiao, J. Wu, Chin. Chem. Lett. 31 (2020) 3083–3094. doi: 10.1016/j.cclet.2020.07.035
49. [49]
  X.Y. Yu, J.R. Chen, P.Z. Wang, et al., Angew. Chem. Int. Ed. 57 (2018) 738–743. doi: 10.1002/anie.201710618
50. [50]
  J. Zhang, X. Li, W. Xie, et al., Org. Lett. 21 (2019) 4950–4954. doi: 10.1021/acs.orglett.9b01323
51. [51]
  L.J. Zhong, H.Y. Wang, X.H. Ouyang, et al., Chem. Commun. 56 (2020) 8671–8674. doi: 10.1039/D0CC03619F
52. [52]
  D. Cyr, P. Das, Res. Chem. Intermediat. 41 (2015) 8603–8623. doi: 10.1007/s11164-014-1914-0
53. [53]
  G. Pandey, D. Pooranchand, U.T. Bhalerao, Tetrahedron 47 (1991) 1745–1752. doi: 10.1016/S0040-4020(01)96916-9
1. [1]
  Chonglong He , Yulong Wang , Quan-Xin Li , Zichen Yan , Keyuan Zhang , Shao-Fei Ni , Xin-Hua Duan , Le Liu . Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/Smiles rearrangement cascade. Chinese Chemical Letters, 2025, 36(5): 110253-. doi: 10.1016/j.cclet.2024.110253
2. [2]
  Yuhan Liu , Jingyang Zhang , Gongming Yang , Jian Wang . Highly enantioselective carbene-catalyzed δ-lactonization via radical relay cross-coupling. Chinese Chemical Letters, 2025, 36(1): 109790-. doi: 10.1016/j.cclet.2024.109790
3. [3]
  Zhengzhong Zhu , Shaojun Hu , Zhi Liu , Lipeng Zhou , Chongbin Tian , Qingfu Sun . A cationic radical lanthanide organic tetrahedron with remarkable coordination enhanced radical stability. Chinese Chemical Letters, 2025, 36(2): 109641-. doi: 10.1016/j.cclet.2024.109641
4. [4]
  Jindian Duan , Xiaojuan Ding , Pui Ying Choy , Binyan Xu , Luchao Li , Hong Qin , Zheng Fang , Fuk Yee Kwong , Kai Guo . Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway. Chinese Chemical Letters, 2024, 35(10): 109565-. doi: 10.1016/j.cclet.2024.109565
5. [5]
  Xiao-Bo Liu , Ren-Ming Liu , Xiao-Di Bao , Hua-Jian Xu , Qi Zhang , Yu-Feng Liang . Nickel-catalyzed reductive formylation of aryl halides via formyl radical. Chinese Chemical Letters, 2024, 35(12): 109783-. doi: 10.1016/j.cclet.2024.109783
6. [6]
  Hong-Qiang Dong , Shang-Bo Yu , Shu-Meng Wang , Jia-Hao Zhao , Xu-Guan Bai , Shi-Xing Lei , Zhen-Nan Tian , Jia Tian , Kang-Da Zhang , Lu Wang , Zhan-Ting Li , Shigui Chen . Construction of radical halogen-bonded organic frameworks with enhanced magnetism and conductivity. Chinese Chemical Letters, 2025, 36(8): 110730-. doi: 10.1016/j.cclet.2024.110730
7. [7]
  Jing-Qi Tao , Shuai Liu , Tian-Yu Zhang , Hong Xin , Xu Yang , Xin-Hua Duan , Li-Na Guo . Photoinduced copper-catalyzed alkoxyl radical-triggered ring-expansion/aminocarbonylation cascade. Chinese Chemical Letters, 2024, 35(6): 109263-. doi: 10.1016/j.cclet.2023.109263
8. [8]
  Wei Zhou , Xi Chen , Lin Lu , Xian-Rong Song , Mu-Jia Luo , Qiang Xiao . Recent advances in electrocatalytic generation of indole-derived radical cations and their applications in organic synthesis. Chinese Chemical Letters, 2024, 35(4): 108902-. doi: 10.1016/j.cclet.2023.108902
9. [9]
  Yu-Yu Tan , Lin-Heng He , Wei-Min He . Copper-mediated assembly of SO₂F group via radical fluorine-atom transfer strategy. Chinese Chemical Letters, 2024, 35(9): 109986-. doi: 10.1016/j.cclet.2024.109986
10. [10]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
11. [11]
  Yaxuan Jin , Chao Zhang , Guigang Zhang . Atomically dispersed low-valent Au on poly(heptazine imide) boosts photocatalytic hydroxyl radical production. Chinese Journal of Structural Chemistry, 2024, 43(12): 100414-100414. doi: 10.1016/j.cjsc.2024.100414
12. [12]
  Jinshuai Zheng , Junfeng Niu , Crispin Halsall , Yadi Guo , Peng Zhang , Linke Ge . New insights into transformation mechanisms for sulfate and chlorine radical-mediated degradation of sulfonamide and fluoroquinolone antibiotics. Chinese Chemical Letters, 2025, 36(5): 110202-. doi: 10.1016/j.cclet.2024.110202
13. [13]
  Shaofeng Gong , Zi-Wei Deng , Chao Wu , Wei-Min He . Stabilized carbon radical-mediated three-component functionalization of amino acid/peptide derivatives. Chinese Chemical Letters, 2025, 36(5): 110936-. doi: 10.1016/j.cclet.2025.110936
14. [14]
  Xiang Li , Beibei Zhang , Zhixiang Wang , Xiangyu Chen . Organocatalyzed iodine-mediated reversible-deactivation radical polymerization via photoinduced charge transfer complex catalysis. Chinese Chemical Letters, 2025, 36(6): 110383-. doi: 10.1016/j.cclet.2024.110383
15. [15]
  Shan-Shan Li , Juan Luo , Shu-Nuo Liang , Dan-Na Chen , Li-Ning Chen , Cheng-Xue Pan , Peng-Ju Xia . Efficient and regioselective C=S bond difunctionalization through a three-component radical relay strategy. Chinese Chemical Letters, 2025, 36(6): 110424-. doi: 10.1016/j.cclet.2024.110424
16. [16]
  Chaojian Xu , Juxin Yin , Sihong Wang , Yue Pan , Qianhe Zhang , Ningkang Xie , Shuo Yang , Shaowu Lv . Aerobic radical polymerization of hydrogels triggered by acetylacetone-transition metal self-initiation. Chinese Chemical Letters, 2025, 36(7): 111075-. doi: 10.1016/j.cclet.2025.111075
17. [17]
  Ying Chen , Lun Li , Guohao Han , Ren Liu , Guanghui An , Yi Zhu . Macromolecular coumarin sulfonium salt with side chain effect constructed by copolymerization strategy for free radical, cationic, and hybrid photopolymerizations. Chinese Chemical Letters, 2025, 36(7): 110458-. doi: 10.1016/j.cclet.2024.110458
18. [18]
  Pei Xu , Tian-Zi Hao , Zhi-Tao Liu , Yi-Qin Liu , Hui-Xian Jiang , Dong Guo , Xu Zhu . Visible-light-induced dual catalysis for divergent reduction of nitro compounds with CO₂ radical anion. Chinese Chemical Letters, 2025, 36(10): 110899-. doi: 10.1016/j.cclet.2025.110899
19. [19]
  Hongping Zhao , Weiming Yuan . Merging catalytic electron donor-acceptor complex and copper catalysis: Enantioselective radical carbocyanation of alkenes. Chinese Chemical Letters, 2025, 36(10): 110894-. doi: 10.1016/j.cclet.2025.110894
20. [20]
  Jingtai Bi , Yupeng Cheng , Mengmeng Sun , Xiaofu Guo , Shizhao Wang , Yingying Zhao . Efficient and selective photocatalytic nitrite reduction to N₂ through CO₂ anion radical by eco-friendly tartaric acid activation. Chinese Chemical Letters, 2024, 35(11): 109639-. doi: 10.1016/j.cclet.2024.109639

Get Citation

PDF

XML

Metrics

PDF Downloads(12)
Abstract views(2153)
HTML views(73)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142