Citation: Song Xi, La Yin, Changhong Xie, Quanying Long, Yulian Zhang, Ling He, Chenyang Wang, Min Zhang. Copper-catalyzed aerobic oxyalkylation of alkenes with cyclopropanols: A straightforward access to 1,5-diketones[J]. Chinese Chemical Letters, ;2026, 37(10): 112433. doi: 10.1016/j.cclet.2026.112433 shu

Copper-catalyzed aerobic oxyalkylation of alkenes with cyclopropanols: A straightforward access to 1,5-diketones

Song Xi ^a ,
La Yin ^a ,
Changhong Xie ^a ,
Quanying Long ^a ,
Yulian Zhang ^a ,
Ling He ^a ,
Chenyang Wang ^{a, *,} ,
Min Zhang ^{a, b, *,}

a.
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, China
b.
Department of Pharmacy, Chongqing General Hospital, Chongqing University, Chongqing 401147, China

wang.chenyang@cqu.edu.cn

minzhang@cqu.edu.cn

Received Date: 14 November 2025
Revised Date: 8 January 2026
Accepted Date: 18 January 2026
Available Online: 19 January 2026

Figures(5)

We report here an aerobic oxyalkylation reaction of alkenes with cyclopropanols that enables the facile synthesis of 1,5-diketones. Key to success of this reaction is utilization of a CuCl₂·Phen catalyst, with the ambient air serving as both the oxidant and oxygen source. The reaction proceeds via a domino process involving a free-radical ring-opening addition of cyclopropanols to alkenes and radical capture by O₂. Both intra- and intermolecular variants are feasible, providing stream-lined access to a broad range of 1,5-diketones possessing fused, spiro, bridged, and linear frameworks. The synthetic utility of this method is showcased by late-stage functionalization of bioactive molecules and synthesis of natural products (analogues).
- Cyclopropanol,
- Oxyalkylation of alkene,
- 1,5-Diketone,
- Copper,
- Natural product
1. [1]
  Y. Wang, L. Zhang, Y. Yang, et al., J. Am. Chem. Soc. 135 (2013) 18048–18051. doi: 10.1021/ja410195j
2. [2]
  A. Tlahuext-Aca, R. A. Garza-Sanchez, F. Glorius, Angew. Chem. Int. Ed. 56 (2017) 3708–3711. doi: 10.1002/anie.201700049
3. [3]
  Y.X. Dong, Y. Li, C.C. Gu, et al., Org. Lett. 20 (2018) 7594–7597. doi: 10.1021/acs.orglett.8b03330
4. [4]
  X. Bao, T. Yokoe, T. M. Ha, et al., Nat. Commun. 9 (2018) 3725. doi: 10.1038/s41467-018-06246-6
5. [5]
  T. Hao, Y. Wei, M. Shi, Green Synth. Catal. (2025) 10.1016/j.gresc.2025.03.010. doi: 10.1016/j.gresc.2025.03.010
6. [6]
  S. Mori, R. Hashimoto, T. Hisatomi, K. Domen, S. Saito, Nat. Commun. 16 (2025) 1797. doi: 10.1038/s41467-025-56374-z
7. [7]
  B. Schweitzer-Chaput, J. Demaerel, H. Engler, M. Klussmann, Angew. Chem. Int. Ed. 53 (2014) 8737–8740. doi: 10.1002/anie.201401062
8. [8]
  J. Xie, Z.Z. Huang, Chem. Commun. 46 (2010) 1947–1949. doi: 10.1039/b921310d
9. [9]
  F. Zhang, P. Du, J. Chen, et al., Org. Lett. 16 (2014) 1932–1935. doi: 10.1021/ol5004687
10. [10]
  X.W. Lan, N.X. Wang, W. Zhang, et al., Org. Lett. 17 (2015) 4460–4463. doi: 10.1021/acs.orglett.5b02116
11. [11]
  S. Sau, K. M. Das, B. Mondal, A. Thakur, J. Org. Chem. 89 (2024) 7095–7108. doi: 10.1021/acs.joc.4c00487
12. [12]
  S. Roy Chowdhury, D. Singh, I. U. Hoque, S. Maity, J. Org. Chem. 85 (2020) 13939–13950. doi: 10.1021/acs.joc.0c01985
13. [13]
  P. Palani, A. Arumugam, D. Raja, K. Muthu, G. C. Senadi, Chem. Commun. 59 (2023) 11433–11436. doi: 10.1039/d3cc02366d
14. [14]
  A. Nikolaev, A. Orellana, Synthesis 48 (2016) 1741–1768. doi: 10.1055/s-0035-1560442
15. [15]
  L.R. Mills, S.A.L. Rousseaux, Eur. J. Org. Chem. 2019 (2019) 8–26. doi: 10.1002/ejoc.201801312
16. [16]
  T. R. McDonald, L. R. Mills, M.S. West, S. A. L. Rousseaux, Chem. Rev. 121 (2021) 3–79. doi: 10.1021/acs.chemrev.0c00346
17. [17]
  Y. Sekiguchi, N. Yoshikai, Bull. Chem. Soc. Jpn. 94 (2021) 265–280. doi: 10.1246/bcsj.20200270
18. [18]
  S. T. Sivanandan, R. B. Krishna, T. V. Baiju, C. Mohan, Eur. J. Org. Chem. 2021 (2021) 6781–6805. doi: 10.1002/ejoc.202100986
19. [19]
  C. Ebner, E. M. Carreira, Chem. Rev. 117 (2017) 11651–11679. doi: 10.1021/acs.chemrev.6b00798
20. [20]
  X.P. Cai, W.D. Liang, M.J. Dai, Tetrahedron 75 (2019) 193–208. doi: 10.1016/j.tet.2018.11.026
21. [21]
  T. Zhou, Q. Tan, D. Jiang, L. He, M. Zhang, Acc. Chem. Res. 58 (2025) 499–515. doi: 10.1021/acs.accounts.4c00732
22. [22]
  C. Che, Z. Qian, M. Wu, Y. Zhao, G. Zhu, J. Org. Chem. 83 (2018) 5665–5673. doi: 10.1021/acs.joc.8b00666
23. [23]
  S. F. Kirsch. Org. Biomol. Chem. 4 (2006) 2076–2080. doi: 10.1039/b602596j
24. [24]
  F. Bellina, R. Rossi, Tetrahedron 62 (2006) 7213–7256.
25. [25]
  W.B. Han, S.G. Li, X.W. Lu, Y. Wu, Eur. J. Org. Chem. 2014 (2014) 3841–3846. doi: 10.1002/ejoc.201402175
26. [26]
  S. Zhai, S. Qiu, S. Yang, et al., Chin. Chem. Lett. 34 (2023) 107657. doi: 10.1016/j.cclet.2022.06.080
27. [27]
  V. A. Zavalinich, G. Z. Elek, P. Vailhé, et al., Adv. Synth. Catal. 366 (2024) 4485–4496. doi: 10.1002/adsc.202400490
28. [28]
  Q. Tan, Z. Yang, D. Jiang, et al., Angew. Chem. Int. Ed. 58 (2019) 6420–6424. doi: 10.1002/anie.201902155
29. [29]
  W. Zhou, T. Zhou, M. Tian, et al., J. Am. Chem. Soc. 143 (2021) 19975–19982. doi: 10.1021/jacs.1c10279
30. [30]
  H. Qiu, X. Fei, J. Yang, et al., Nat. Commun. 14 (2023) 5560. doi: 10.1038/s41467-023-41268-9
31. [31]
  D. Jiang, P. Tang, H. Xiong, et al., Angew. Chem. Int. Ed. 62 (2023) e202307286. doi: 10.1002/anie.202307286
32. [32]
  S. Chiba, M. Kitamura, K. Narasaka, J. Am. Chem. Soc. 128 (2006) 6931–6937. doi: 10.1021/ja060408h
33. [33]
  Y.F. Wang, K. K. Toh, E. P. J. Ng, S. Chiba, J. Am. Chem. Soc. 133 (2011) 6411–6421. doi: 10.1021/ja200879w
34. [34]
  L.N. Guo, Z.Q. Deng, Y. Wu, J. Hu, RSC Adv. 6 (2016) 27000–27003. doi: 10.1039/C6RA03431D
35. [35]
  Ł. Woźniak, G. Magagnano, P. Melchiorre, Angew. Chem. Int. Ed. 57 (2018) 1068–1072. doi: 10.1002/anie.201711397
36. [36]
  Y. Sekiguchi, N. Yoshikai, J. Am. Chem. Soc. 143 (2021) 4775–4781. doi: 10.1021/jacs.1c00869
37. [37]
  J. Sheng, J.D. Liu, L.Q. Chen, et al., Org. Chem. Front. 6 (2019) 1471–1475. doi: 10.1039/c9qo00292h
38. [38]
  J.F. Yang, Y. Sekiguchi, N. Yoshikai, ACS Catal. 9 (2019) 5638–5644. doi: 10.1021/acscatal.9b00655
39. [39]
  W. Huang, F.K. Meng, Angew. Chem. Int. Ed. 60 (2021) 2694–2698. doi: 10.1002/anie.202012122
40. [40]
  T. Kikuchi, K. Yamada, T. Yasui, Y. Yamamoto, Org. Lett. 23 (2021) 4710–4714. doi: 10.1021/acs.orglett.1c01436
41. [41]
  C. Lou, X. Wang, L. Lv, Z. Li, Org. Lett. 23 (2021) 7608–7612. doi: 10.1021/acs.orglett.1c02824
42. [42]
  X. Zhang, T.M. Yang, L.M. Hu, X.H. Hu, Org. Lett. 24 (2022) 8677–8682. doi: 10.1021/acs.orglett.2c03563
43. [43]
  J. Yang, S. Wu, Y.L. Chu, M. Hu, J.H. Li, J. Org. Chem. 90 (2025) 6871–6880. doi: 10.1021/acs.joc.5c00853
44. [44]
  G. Xu, P. Guan, L. Deng, et al., Org. Lett. 27 (2025) 4682–4687. doi: 10.1021/acs.orglett.5c00975
45. [45]
  J. Yang, Y. Shen, Y.J. Lim, N. Yoshikai, Chem. Sci. 9 (2018) 6928–6934. doi: 10.1039/c8sc02074d
46. [46]
  J. Ding, X. Li, H. Lin, et al., Chin. Chem. Lett. 36 (2025) 111286. doi: 10.1016/j.cclet.2025.111286
47. [47]
  J. Yang, Q. Sun, N. Yoshikai, ACS Catal. 9 (2019) 1973–1978. doi: 10.1021/acscatal.8b05114
48. [48]
  N. Iwasawa, S. Hayakawa, K. Isobe, K. Narasaka, Chem. Lett. 20 (1991) 1193–1196. doi: 10.1246/cl.1991.1193
49. [49]
  N. Iwasawa, S. Hayakawa, M. Funahashi, K. Isobe, K. Narasaka, Bull. Chem. Soc. Jpn. 66 (1993) 819–827. doi: 10.1246/bcsj.66.819
50. [50]
  S. Chiba, Z. Cao, S. A. A. El Bialy, K. Narasaka, Chem. Lett. 35 (2006) 18–19. doi: 10.1246/cl.2006.18
51. [51]
  L. Fang, S. Fan, W. Wu, T. Li, J. Zhu, Chem. Commun. 57 (2021) 7386–7389. doi: 10.1039/d1cc02576g
52. [52]
  R. Guo, G. Zhang, J. Am. Chem. Soc. 139 (2017) 12891–12894. doi: 10.1021/jacs.7b05427
53. [53]
  A. Kitabayashi, S. Mizushima, K. Higashida, et al., Adv. Synth. Catal. 364 (2022) 1855–1862. doi: 10.1002/adsc.202200157
54. [54]
  Y.H. Zhang, W.W. Zhang, Z.Y. Zhang, K. Zhao, T.P. Loh, Org. Lett. 21 (2013) 5101–5105.
55. [55]
  Y. Sekiguchi, Y. Y. Lee, N. Yoshikai, Org. Lett. 23 (2021) 5993–5997. doi: 10.1021/acs.orglett.1c02072
56. [56]
  W.H. Jiao, T.T. Xu, H.B. Yu, et al., J. Nat. Prod. 77 (2014) 346–350. doi: 10.1021/np4009392
57. [57]
  X.H. Tian, L.L. Hong, W.H. Jiao, H.W. Lin, Nat. Prod. Rep. 40 (2023) 718–749. doi: 10.1039/d2np00045h
58. [58]
  W.H. Jiao, Q.H. Xu, J. Cui, et al., Org. Chem. Front. 7 (2020) 368–373. doi: 10.1039/c9qo01346f
59. [59]
  L. F. Tietze, D. A. Spiegl, F. Stecker, et al., Chem. Eur. J. 14 (2008) 8956–8963. doi: 10.1002/chem.200800967
60. [60]
  J. D. Brown, M. A. Foley, D. L. Comins, J. Am. Chem. Soc. 110 (1988) 7445–7447. doi: 10.1021/ja00230a026
61. [61]
  M. N. V. G, R. Dyapa, S. V. Pansare, Org. Lett. 17 (2015) 5312–5315. doi: 10.1021/acs.orglett.5b02677
62. [62]
  T. Takeuchi, M. Matsuhashi, T. Nakata, Tetrahedron Lett. 49 (2008) 6462–6465.
63. [63]
  S. Sun, Y. Yang, R. Zhao, D. Zhang, L. Liu, J. Am. Chem. Soc. 142 (2020) 19346–19353. doi: 10.1021/jacs.0c09636
64. [64]
  C. Tang, X. Qiu, Z. Cheng, N. Jiao, Chem. Soc. Rev. 50 (2021) 8067–8101. doi: 10.1039/d1cs00242b
65. [65]
  Z.L. Li, G.C. Fang, Q.S. Gu, X.Y. Liu, Chem. Soc. Rev. 49 (2020) 32–48. doi: 10.1039/c9cs00681h
66. [66]
  Y. Su, X. Sun, G. Wu, N. Jiao, Angew. Chem. Int. Ed. 52 (2013) 9808–9812. doi: 10.1002/anie.201303917
67. [67]
  H. R. Lucas, L. Li, A. A. Narducci Sarjeant, et al., J. Am. Chem. Soc. 131 (2009) 3230–3245. doi: 10.1021/ja807081d
68. [68]
  J. Shen, D. Yang, Y. Liu, et al., Org. Lett. 16 (2014) 350–353. doi: 10.1021/ol403555n
69. [69]
  G. Zhang, C. Yang, E. Liu, et al., RSC Adv. 4 (2014) 61907–61911.
70. [70]
  O. Das, T. K. Paine, Dalton Trans. 41 (2012) 11476–11481. doi: 10.1039/c2dt31134h
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