Citation: Huaixiang Yang, Miao-Miao Li, Aijun Zhang, Jiefei Guo, Yongqi Yu, Wei Ding. Visible-light-induced photocatalyst- and metal-free radical phosphinoyloximation of alkenes with tert-butyl nitrite as bifunctional reagent[J]. Chinese Chemical Letters, ;2025, 36(3): 110425. doi: 10.1016/j.cclet.2024.110425 shu

Visible-light-induced photocatalyst- and metal-free radical phosphinoyloximation of alkenes with tert-butyl nitrite as bifunctional reagent

Huaixiang Yang ^a ,
Miao-Miao Li ^{a, *,} ,
Aijun Zhang ^a ,
Jiefei Guo ^a ,
Yongqi Yu ^{b, *,} ,
Wei Ding ^{a, *,}

a.
Division of Molecular Catalysis and Synthesis, Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou 450001, China
b.
College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang 473061, China

miaomiaoli116@zzu.edu.cn

yuyq2021@163.com

ding_w@zzu.edu.cn

Received Date: 30 June 2024
Revised Date: 23 August 2024
Accepted Date: 6 September 2024
Available Online: 15 October 2024

Figures(6)

The tert-butyl nitrite as a bifunctional reagent mediated radical alkene difunctionalization has emerged as a powerful strategy for synthesis of structurally diverse oxime-containing compounds. However, the phosphorus-centered radical initiated transformations remain largely elusive. Herein, a visible-light-induced radical phosphinoyloximation of alkenes with secondary phosphine oxides and tert-butyl nitrite has been developed under photocatalyst- and metal-free conditions. This protocol features mild conditions, broad substrate scope, good functional tolerance, and operational simplicity, yielding a diverse array of α-phosphinoyl oximes in moderate to good yields with high stereoselectivities. The photomediated homolytic cleavage of ONO bond of tert-butyl nitrite generates the reactive tert-butoxyl radical and persistent NO radical to act as both HAT reagent and the source of oximes.
- Photochemistry,
- Phosphorus-centered radical,
- Phosphinoyloximation,
- α-Phosphinoyl oximes,
- Bifunctional reagent
1. [1]
  M.Y. Cao, X. Ren, Z. Lu, Tetrahedron Lett. 56 (2015) 3732–3742. doi: 10.1016/j.tetlet.2015.04.091
2. [2]
  X.W. Lan, N.X. Wang, Y. Xing, Eur. J. Org. Chem. 2017 (2017) 5821–5851. doi: 10.1002/ejoc.201700678
3. [3]
  T. Koike, M. Akita, Chem 4 (2018) 409–437. doi: 10.1016/j.chempr.2017.11.004
4. [4]
  J. Lin, R.J. Song, M. Hu, J.H. Li, Chem. Rec. 19 (2018) 440–451. doi: 10.1002/tcr.201800053
5. [5]
  X. Bao, J. Li, W. Jiang, C. Huo, Synthesis 51 (2019) 4507–4530. doi: 10.1055/s-0039-1690987
6. [6]
  H. Yao, W. Hu, W. Zhang, Molecules 26 (2020) 105. doi: 10.3390/molecules26010105
7. [7]
  S.O. Badir, G.A. Molander, Chem 6 (2020) 1327–1339. doi: 10.1016/j.chempr.2020.05.013
8. [8]
  H. Jiang, A. Studer, Chem. Soc. Rev. 49 (2020) 1790–1811. doi: 10.1039/c9cs00692c
9. [9]
  Z.L. Li, G.C. Fang, Q.S. Gu, X.Y. Liu, Chem. Soc. Rev. 49 (2020) 32–48. doi: 10.1039/c9cs00681h
10. [10]
  S. Zhu, X. Zhao, H. Li, L. Chu, Chem. Soc. Rev. 50 (2021) 10836–10856. doi: 10.1039/d1cs00399b
11. [11]
  P. Gao, Y.J. Niu, F. Yang, L.N. Guo, X.H. Duan, Chem. Commun. 58 (2022) 730–746. doi: 10.1039/d1cc05730h
12. [12]
  K. Katakawa, M. Kitajima, N. Aimi, et al., J. Org. Chem. 70 (2004) 658–663.
13. [13]
  J.T. Bagdanoff, M.S. Donoviel, A. Nouraldeen, et al., J. Med. Chem. 53 (2010) 8650–8662. doi: 10.1021/jm101183p
14. [14]
  C. Kornhaaß, J. Li, L. Ackermann, J. Org. Chem. 77 (2012) 9190–9198. doi: 10.1021/jo301768b
15. [15]
  Y. Wei, N. Yoshikai, J. Am. Chem. Soc. 135 (2013) 3756–3759. doi: 10.1021/ja312346s
16. [16]
  Y. Xu, W. Hu, X. Tang, et al., Chem. Commun. 51 (2015) 6843–6846. doi: 10.1039/C5CC01661D
17. [17]
  N. Liu, L. Song, M. Liu, et al., Chem. Sci. 7 (2016) 482–488. doi: 10.1039/C5SC03021H
18. [18]
  D.Q. Dong, J.C. Song, S.H. Yang et al., Chin. Chem. Lett. 33 (2022) 1199–1206. doi: 10.1016/j.cclet.2021.08.067
19. [19]
  S. Yang, Y. Wang, W. Xu, et al., Org. Lett. 25 (2023) 8834–8838. doi: 10.1021/acs.orglett.3c03526
20. [20]
  T. Zou, Y.S. He, R. Liu, et al., Chin. Chem. Lett. 34 (2023) 107822–107826. doi: 10.1016/j.cclet.2022.107822
21. [21]
  K. Kato, T. Mukaiyama, Chem. Lett. 19 (1990) 1395–1398. doi: 10.1246/cl.1990.1395
22. [22]
  M. Kijima, H. Yamashita, T. Sato, J. Organomet. Chem. 426 (1992) 399–404. doi: 10.1016/0022-328X(92)83072-P
23. [23]
  T. Okamoto, K. Kobayashi, S. Oka, S. Tanimoto, J. Org. Chem. 52 (2002) 5089–5092.
24. [24]
  C. de Salas, O. Blank, M.R. Heinrich, Chem. Eur. J. 17 (2011) 9306–9310. doi: 10.1002/chem.201101565
25. [25]
  C. de Salas, M.R. Heinrich, Green Chem. 16 (2014) 2982–2987. doi: 10.1039/C3GC42432D
26. [26]
  J. Hartung, Chem. Rev. 109 (2009) 4500–4517. doi: 10.1021/cr900085j
27. [27]
  P. Scharlin, R. Battino, E. Silla, I. Tuñón, J.L. Pascual-Ahuir, Pure Appl. Chem. 70 (1998) 1895–1904. doi: 10.1351/pac199870101895
28. [28]
  B. Weinberger, Toxicol. Sci. 59 (2001) 5–16. doi: 10.1093/toxsci/59.1.5
29. [29]
  P.F. Yuan, T. Huang, J. He, et al., Org. Chem. Front. 8 (2021) 5785–5792. doi: 10.1039/d1qo01101d
30. [30]
  Z. Wang, N. Wierich, J. Zhang, C.G. Daniliuc, A. Studer, J. Am. Chem. Soc. 145 (2023) 8770–8775. doi: 10.1021/jacs.3c01129
31. [31]
  H. Lan, X. Huo, Y. Jia, D. Wang, Org. Lett. 26 (2024) 1011–1016. doi: 10.1021/acs.orglett.3c04085
32. [32]
  P.F. Yuan, X.T. Huang, L.H. Long, et al., Angew. Chem. Int. Ed. 63 (2024) e202317968. doi: 10.1002/anie.202317968
33. [33]
  J.W. Sang, H. Chen, Y. Zhang, J. Wang, W.D. Zhang, Green Chem. 26 (2024) 7849–7856. doi: 10.1039/d4gc01976h
34. [34]
  H. Chakrapani, M.D. Bartberger, E.J. Toone, J. Org. Chem. 74 (2009) 1450–1453. doi: 10.1021/jo802517t
35. [35]
  D. Zheng, S. Plöger, C.G. Daniliuc, A. Studer, Angew. Chem. Int. Ed. 60 (2021) 8547–8551. doi: 10.1002/anie.202016955
36. [36]
  R. Gao, F. Wang, X. Geng, C.Y. Li, L. Wang, Org. Lett. 24 (2022) 7118–7122. doi: 10.1021/acs.orglett.2c02703
37. [37]
  S. Plöger, C. Mück-Lichtenfeld, C.G. Daniliuc, A. Studer, Chem. Sci. 13 (2022) 9749–9754. doi: 10.1039/d2sc03860a
38. [38]
  D.H.R. Barton, J.M. Beaton, J. Am. Chem. Soc. 82 (1960) 2641. doi: 10.1021/ja01495a062
39. [39]
  D.H.R. Barton, J.M. Beaton, L.E. Geller, M.M. Pechet, J. Am. Chem. Soc. 82 (1960) 2640–2641. doi: 10.1021/ja01495a061
40. [40]
  D.H.R. Barton, J.M. Beaton, L.E. Geller, M.M. Pechet, J. Am. Chem. Soc. 83 (1961) 4076–4083. doi: 10.1021/ja01480a030
41. [41]
  G. Majetich, K. Wheless, Tetrahedron 51 (1995) 7095–7129. doi: 10.1016/0040-4020(95)00406-X
42. [42]
  E. Piers, Pure Appl. Chem. 60 (1988) 107–114. doi: 10.1351/pac198860010107
43. [43]
  H.M. Huang, P. Bellotti, J. Ma, T. Dalton, F. Glorius, Nat. Rev. Chem. 5 (2021) 301–321. doi: 10.1038/s41570-021-00266-5
44. [44]
  A. Dahiya, A.K. Sahoo, T. Alam, B.K. Patel, Chem. Asian J. 14 (2019) 4454–4492. doi: 10.1002/asia.201901072
45. [45]
  N.G. Khaligh, Mini-Rev. Org. Chem. 17 (2020) 3–25. doi: 10.2174/1570193x15666181029141019
46. [46]
  Z.L. Chen, Q.Q. Li, A. Studer, J. Xuan, Sci. China Chem. 68 (2025) 118–133. doi: 10.1007/s11426-024-2096-6
47. [47]
  J. Yang, Y.Y. Liu, R.J. Song, Z.H. Peng, J.H. Li, Adv. Synth. Catal. 358 (2016) 2286–2292. doi: 10.1002/adsc.201600109
48. [48]
  B. Wang, L. Tang, L. Liu, et al., Green Chem. 19 (2017) 5794–5799. doi: 10.1039/C7GC03051G
49. [49]
  J. Wysocki, J.H. Teles, R. Dehn, et al., ChemPhotoChem 2 (2018) 22–26. doi: 10.1002/cptc.201700151
50. [50]
  L. Chen, Z. Wang, H. Liu, X. Li, B. Wang, Chem. Commun. 58 (2022) 9152–9155. doi: 10.1039/d2cc02823a
51. [51]
  Y. Liu, J. Cao, M. Zhang, et al., J. Org. Chem. 88 (2023) 15311–15317. doi: 10.1021/acs.joc.3c01815
52. [52]
  Y. Tang, Y. Yang, Q. Zhou, et al., Org. Biomol. Chem. 21 (2023) 5254–5264. doi: 10.1039/d3ob00630a
53. [53]
  Y. Zhao, X. Li, S.L. Homölle, B. Wang, L. Ackermann, Chem. Sci. 15 (2024) 1117–1122. doi: 10.1039/d3sc05946d
54. [54]
  X. m. Chen, J. Huang, J. Pan, et al., Org. Lett. 26 (2024) 3883–3888. doi: 10.1021/acs.orglett.4c01038
55. [55]
  S. Plöger, A. Studer, Org. Lett. 24 (2022) 8568–8572. doi: 10.1021/acs.orglett.2c03644
56. [56]
  W. Li, Z. Huang, D. Zhong, H. Li, Org. Lett. 26 (2024) 2062–2067. doi: 10.1021/acs.orglett.4c00314
57. [57]
  P.C.J. Kamer, P.W.N.M. van Leeuwen, J.N.H. Reek, Acc. Chem. Res. 34 (2001) 895–904. doi: 10.1021/ar000060+
58. [58]
  P.W.N.M. van Leeuwen, P.C.J. Kamer, C. Claver, O. Pàmies, M. Diéguez, Chem. Rev. 111 (2011) 2077–2118. doi: 10.1021/cr1002497
59. [59]
  C. Queffélec, M. Petit, P. Janvier, D.A. Knight, B. Bujoli, Chem. Rev. 112 (2012) 3777–3807. doi: 10.1021/cr2004212
60. [60]
  G.P. Horsman, D.L. Zechel, Chem. Rev. 117 (2017) 5704–5783. doi: 10.1021/acs.chemrev.6b00536
61. [61]
  H. Ni, W.L. Chan, Y. Lu, Chem. Rev. 118 (2018) 9344–9411. doi: 10.1021/acs.chemrev.8b00261
62. [62]
  H. Guo, Y.C. Fan, Z. Sun, Y. Wu, O. Kwon, Chem. Rev. 118 (2018) 10049–10293. doi: 10.1021/acs.chemrev.8b00081
63. [63]
  P. Finkbeiner, J.P. Hehn, C. Gnamm, J. Med. Chem. 63 (2020) 7081–7107. doi: 10.1021/acs.jmedchem.0c00407
64. [64]
  K. Moonen, I. Laureyn, C.V. Stevens, Chem. Rev. 104 (2004) 6177–6216. doi: 10.1021/cr030451c
65. [65]
  C.S. Demmer, N. Krogsgaard-Larsen, L. Bunch, Chem. Rev. 111 (2011) 7981–8006. doi: 10.1021/cr2002646
66. [66]
  J.L. Montchamp, Acc. Chem. Res. 47 (2014) 77–87. doi: 10.1021/ar400071v
67. [67]
  H. Sun, Y. Li, W. Liu, Y. Zheng, Z. He, Chin. Chem. Lett. 29 (2018) 1625–1628. doi: 10.1016/j.cclet.2018.01.026
68. [68]
  L. Chen, X.Y. Liu, Y.X. Zou, Adv. Synth. Catal. 362 (2020) 1724–1818. doi: 10.1002/adsc.201901540
69. [69]
  J.D. Gbubele, T.K. Olszewski, Org. Biomol. Chem. 19 (2021) 2823–2846. doi: 10.1039/d1ob00124h
70. [70]
  B. Wang, L. Sun, Q. Cao, et al., Chin. Chem. Lett. 35 (2024) 109617. doi: 10.1016/j.cclet.2024.109617
71. [71]
  D. Leca, L. Fensterbank, E. Lacôte, M. Malacria, Chem. Soc. Rev. 34 (2005) 858–865. doi: 10.1039/b500511f
72. [72]
  Y. Gao, G. Tang, Y. Zhao, Phosphorus, Sulfur, Silicon Relat. Elem. 192 (2017) 589–596. doi: 10.1080/10426507.2017.1295965
73. [73]
  B.G. Cai, J. Xuan, W.J. Xiao, Sci. Bull. 64 (2019) 337–350. doi: 10.1016/j.scib.2019.02.002
74. [74]
  C. Li, J. Wang, S.D. Yang, Chem. Commun. 57 (2021) 7997–8002. doi: 10.1039/d1cc02604f
75. [75]
  J. Liu, H.Z. Xiao, Q. Fu, D.G. Yu, Chem. Synth. 1 (2021) 9. doi: 10.20517/cs.2021.14
76. [76]
  Y. Niu, S. -D. Yang, Chem. Synth. 1 (2021) 12.
77. [77]
  C. Zhang, Z. Li, L. Zhu, et al., J. Am. Chem. Soc. 135 (2013) 14082–14085. doi: 10.1021/ja408031s
78. [78]
  W.J. Yoo, S. Kobayashi, Green Chem. 15 (2013) 1844–1848. doi: 10.1039/c3gc40482j
79. [79]
  G. Zhang, L. Fu, P. Chen, J. Zou, G. Liu, Org. Lett. 21 (2019) 5015–5020. doi: 10.1021/acs.orglett.9b01607
80. [80]
  Y.H. Li, C.H. Wang, S.Q. Gao, F.M. Qi, S.D. Yang, Chem. Commun. 55 (2019) 11888–11891. doi: 10.1039/c9cc06075h
81. [81]
  Q. Fu, Z.Y. Bo, J.H. Ye, et al., Nat. Commun. 10 (2019) 3592. doi: 10.1038/s41467-019-11528-8
82. [82]
  W.Q. Liu, T. Lei, S. Zhou, et al., J. Am. Chem. Soc. 141 (2019) 13941–13947. doi: 10.1021/jacs.9b06920
83. [83]
  N. Fu, L. Song, J. Liu, et al., J. Am. Chem. Soc. 141 (2019) 14480–14485. doi: 10.1021/jacs.9b03296
84. [84]
  W. Yang, B. Li, M. Zhang, et al., Chin. Chem. Lett. 31 (2020) 1313–1316. doi: 10.1016/j.cclet.2019.10.022
85. [85]
  P.Z. Wang, W.J. Xiao, J.R. Chen, Nat. Rev. Chem. 7 (2022) 35–50. doi: 10.1038/s41570-022-00441-2
86. [86]
  Q. Cao, M.M. Li, X. Mao, Q.Q. Zhou, W. Ding, Org. Lett. 26 (2024) 4678–4683. doi: 10.1021/acs.orglett.4c01422
87. [87]
  H. Zhang, X. Sun, C. Ma, et al., ACS Catal. 14 (2024) 3115–3127. doi: 10.1021/acscatal.3c05154
88. [88]
  G.Q. Li, Z.Q. Li, M. Jiang, et al., Angew. Chem. Int. Ed. 63 (2024) e202405560. doi: 10.1002/anie.202405560
89. [89]
  L. Liu, Y. Wu, C. Xiang, J.T. Yu, C. Pan, Chem. Commun. 60 (2024) 4687–4690. doi: 10.1039/d4cc00608a
90. [90]
  X.M. Chen, L. Song, J. Pan, et al., Chin. Chem. Lett. 35 (2024) 110112. doi: 10.1016/j.cclet.2024.110112
91. [91]
  D. Liang, P. Gao, Z. Zhang, W. Xiao, J. Chen, Green Synth. Catal. 5 (2024), doi:10.1016/j.gresc.2024.01.002. doi: 10.1016/j.gresc.2024.01.002
92. [92]
  A.V. Il'yasov, Biophysics 58 (2013) 167–171. doi: 10.1134/S0006350913020103
93. [93]
  J. Francos, J. Borge, S. Conejero, V. Cadierno, Eur. J. Inorg. Chem. 2018 (2018) 3176–3186. doi: 10.1002/ejic.201800398
94. [94]
  Y.A. Naumovich, S.L. Ioffe, A.Y. Sukhorukov, J. Org. Chem. 84 (2019) 7244–7254. doi: 10.1021/acs.joc.9b00924
95. [95]
  H. Lan, Y. Su, Y. Chen, X. He, D. Wang, Org. Chem. Front. 11 (2024) 4207–4213. doi: 10.1039/d4qo00636d
96. [96]
  J. Zou, Z. Ying, P. Zhang, Z. Tao, J. Li, Patent, CN111039978B, 2017.
97. [97]
  J. Shen, B. Xiao, Y. Hou, et al., Adv. Synth. Catal. 361 (2019) 5198–5209. doi: 10.1002/adsc.201900873
98. [98]
  D. Leifert, A. Studer, Angew. Chem. Int. Ed. 59 (2020) 74–108. doi: 10.1002/anie.201903726
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  Zhixiang Li , Zhirong Yang , Chang Yao , Bin Wu , Gang Qian , Xuezhi Duan , Xinggui Zhou , Jing Zhang . Efficient continuous synthesis of 2-hydroxycarbazole and 4-hydroxycarbazole in a millimeter scale photoreactor. Chinese Chemical Letters, 2024, 35(4): 108893-. doi: 10.1016/j.cclet.2023.108893
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  Jing-Jing Zhang , Lujun Lou , Rui Lv , Jiahui Chen , Yinlong Li , Guangwei Wu , Lingchao Cai , Steven H. Liang , Zhen Chen . Recent advances in photochemistry for positron emission tomography imaging. Chinese Chemical Letters, 2024, 35(8): 109342-. doi: 10.1016/j.cclet.2023.109342
5. [5]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
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  Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
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  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
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  Juhong Zhou , Hui Zhao , Ping Han , Ziyue Wang , Yan Zhang , Xiaoxia Mao , Konglin Wu , Shengjue Deng , Wenxiang He , Binbin Jiang . Strategic modulation of CoFe sites for advanced bifunctional oxygen electrocatalyst. Chinese Journal of Structural Chemistry, 2025, 44(1): 100470-100470. doi: 10.1016/j.cjsc.2024.100470
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  Haodong Wang , Xiaoxu Lai , Chi Chen , Pei Shi , Houzhao Wan , Hao Wang , Xingguang Chen , Dan Sun . Novel 2D bifunctional layered rare-earth hydroxides@GO catalyst as a functional interlayer for improved liquid-solid conversion of polysulfides in lithium-sulfur batteries. Chinese Chemical Letters, 2024, 35(5): 108473-. doi: 10.1016/j.cclet.2023.108473
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20. [20]
  Xiaohan Zhang , Bo Xiao . Facilitating ultra-fast lithium ion diffusion in face-centered cubic oxides via over-stoichiometric face-sharing configurations. Chinese Journal of Structural Chemistry, 2025, 44(2): 100419-100419. doi: 10.1016/j.cjsc.2024.100419

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沈阳化工大学材料科学与工程学院沈阳 110142