Citation: Ling-Qi Chen, Chi-Fan Zhu, Su Zhang, Bao-Yang Liu, Shu-Jiang Tu, Wen-Juan Hao, Bo Jiang. Palladium-catalyzed annulative allylic alkylation for regioselective construction of indole-fused medium-sized cyclic ethers[J]. Chinese Chemical Letters, ;2023, 34(12): 108398. doi: 10.1016/j.cclet.2023.108398 shu

Palladium-catalyzed annulative allylic alkylation for regioselective construction of indole-fused medium-sized cyclic ethers

Ling-Qi Chen ^{a, 1} ,
Chi-Fan Zhu ^{a, b, 1} ,
Su Zhang ^a ,
Bao-Yang Liu ^a ,
Shu-Jiang Tu ^{a, *,} ,
Wen-Juan Hao ^{a, *,} ,
Bo Jiang ^{a, *,}

a.
School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou 221116, China
b.
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Pharmacy, Changzhou University, Changzhou 213164, China

^☆

laotu@jsnu.edu.cn

wjhao@jsnu.edu.cn

jiangchem@jsnu.edu.cn

Received Date: 16 January 2023
Revised Date: 18 March 2023
Accepted Date: 28 March 2023
Available Online: 31 March 2023

Figures(7)

A new palladium-catalyzed annulative allylic alkylation (AAA) reaction of 2-(indol-2-yl)phenols with dual allylic electrophiles such as isobutylene dicarbonate and butene dicarbonate is described, leading to the regioselective synthesis of tetracyclic medium-sized cyclic ethers possessing a bridged aryl-indole scaffold, namely, benzo[2,3]oxocino[4,5-b]indoles and benzo[2,3]oxepino[4,5-b]indoles, in good to excellent yields. This protocol demonstrates a broad substrate scope, good compatibility with substituents and high regioselectivity, providing a catalytic and flexible method for creating bridged aryl-indole skeletons.
- Palladium-catalysis,
- Annulative allylic alkylation,
- [5 + n] annulation,
- Regioselectivity,
- Medium-sized cyclic ethers
1. [1]
  S. Sarkhel, A. Sharon, V. Trivedi, et al., Bioorg. Med. Chem. 11 (2003) 5025–5033. doi: 10.1016/j.bmc.2003.08.026
2. [2]
  T.P. Heffron, B.Q. Wei, A. Olivero, et al., J. Med. Chem. 54 (2011) 7815–7833. doi: 10.1021/jm2007084
3. [3]
  L. Hu, Y. Xue, J. Zhang, et al., J. Nat. Prod. 79 (2016) 1322–1328. doi: 10.1021/acs.jnatprod.5b01119
4. [4]
  N.M. O'Boyle, I. Barrett, L.M. Greene, et al., J. Med. Chem. 61 (2018) 514–534. doi: 10.1021/acs.jmedchem.6b01917
5. [5]
  C.L. Gao, G.G. Hou, J. Liu, et al., Angew. Chem. Int. Ed. 59 (2020) 2429–2439. doi: 10.1002/anie.201912489
6. [6]
  T. Kamei, M. Shindo, K. Shishido, Tetrahedron Lett. 44 (2003) 8505–8507. doi: 10.1016/j.tetlet.2003.09.086
7. [7]
  S.P. Kureel, R.S. Kapil, S.P. Popli, Tetrahedron Lett. 10 (1969) 3857–3862. doi: 10.1016/S0040-4039(01)88531-2
8. [8]
  L.C. Fu, X.A. Huang, Z.Y. Lai, et al., Molecules 13 (2008) 1923–1930. doi: 10.3390/molecules13081923
9. [9]
  Z. Wang, J.B. S. un, W. Qu, et al., Fitoterapia 92 (2014) 280–284. doi: 10.1016/j.fitote.2013.12.004
10. [10]
  T.D. Cuong, T.M. Hung, J.C. Kim, et al., J. Nat. Prod. 75 (2012) 2069–2075. doi: 10.1021/np3003673
11. [11]
  U.S. Singh, R. Shankar, A. Kumar, et al., Bioorg. Med. Chem. 16 (2008) 8482–8491. doi: 10.1016/j.bmc.2008.08.024
12. [12]
  G. Illuminati, L. Mandolini, Acc. Chem. Res. 14 (1981) 95–102. doi: 10.1021/ar00064a001
13. [13]
  M.A. Winnik, Chem. Rev. 81 (1981) 491–524. doi: 10.1021/cr00045a004
14. [14]
  S. Yamaguchi, N. Tsuchida, M. Miyazawa, et al., J. Org. Chem. 70 (2005) 7505–7511. doi: 10.1021/jo050550l
15. [15]
  J. Liu, Y. Liu, Org. Lett. 14 (2012) 4742–4745. doi: 10.1021/ol302252h
16. [16]
  K. Bera, S. Jalal, S. Sarkar, U. Org. Biomol. Chem. 12 (2014) 57–61. doi: 10.1039/C3OB41624K
17. [17]
  P.W.H. Chan, W.T. Teo, S.W.Y. Koh, et al., Eur. J. Org. Chem. 2015 (2015) 4447–4456. doi: 10.1002/ejoc.201500374
18. [18]
  M. Chwastek, M. Pieczykolan, S. Stecko, J. Org. Chem. 81 (2016) 9046–9074. doi: 10.1021/acs.joc.6b01691
19. [19]
  Y. Onodera, K. Hirota, Y. Suga, et al., J. Org. Chem. 81 (2016) 8234–8252. doi: 10.1021/acs.joc.6b01302
20. [20]
  T. Zhang, H. Zhuang, L. Tang, et al., Org. Lett. 24 (2022) 207–212. doi: 10.1021/acs.orglett.1c03852
21. [21]
  T. Liang, G. Dong, C. Li, X. Xu, Z. Xu, Org. Lett. 24 (2022) 1817–1821. doi: 10.1021/acs.orglett.2c00270
22. [22]
  W. Yi, L. Li, H. Chen, et al., Org. Lett. 20 (2018) 6812–6816. doi: 10.1021/acs.orglett.8b02940
23. [23]
  B.K. Villuri, S.S. Ichake, S.R. Reddy, et al., J. Org. Chem. 83 (2018) 10241–10247. doi: 10.1021/acs.joc.8b01443
24. [24]
  J.Y. Du, Y.H. Ma, F.X. Meng, et al., Org. Lett. 21 (2019) 465–468. doi: 10.1021/acs.orglett.8b03709
25. [25]
  B.M. Trost, Z. Zuo, Angew. Chem. Int. Ed. 59 (2020) 1243–1247. doi: 10.1002/anie.201911537
26. [26]
  R.J. Yan, B.X. Liu, B.X. Xiao, W. Du, Y.C. Chen, Org. Lett. 22 (2020) 4240–4244. doi: 10.1021/acs.orglett.0c01283
27. [27]
  Z. Shen, L. Zhou, C. Wu, Q. Zhou, H.G. Cheng, Org. Biomol. Chem. 20 (2022) 8869–8872. doi: 10.1039/d2ob01720b
28. [28]
  T. Courant, M. Pasco, T. Lecourt, Org. Lett. 20 (2018) 2757–2761. doi: 10.1021/acs.orglett.8b00984
29. [29]
  A.N. Leveille, M.M. Allegrezza, K. Laybourna, A.E. Mattson, Chem. Commun. 58 (2022) 12600–12603. doi: 10.1039/d2cc02023h
30. [30]
  B.T. Kelley, J.C. Walters, S.E. Wengryniuk, Org. Lett. 18 (2016) 1896–1899. doi: 10.1021/acs.orglett.6b00672
31. [31]
  W.L. Yang, Y.L. Wang, W. Li, et al., ACS Catal. 11 (2021) 12557–12564. doi: 10.1021/acscatal.1c03711
32. [32]
  X. Wang, J. Yang, R. Lv, et al., Org. Chem. Front. 9 (2022) 3493–3498. doi: 10.1039/d2qo00422d
33. [33]
  V.T.H. Nguyen, E. Bellur, P. Langer, Tetrahedron Lett. 47 (2006) 113–116. doi: 10.1016/j.tetlet.2005.10.132
34. [34]
  V.T.H. Nguyen, E. Bellur, C. Fischer, P. Langer, Tetrahedron 63 (2007) 8037–8045. doi: 10.1016/j.tet.2007.05.056
35. [35]
  B.M. Trost, C.A. Kalnmals, Chem. Eur. J. 26 (2020) 1906–1921. doi: 10.1002/chem.201903961
36. [36]
  K. Xu, J.X. Ye, H. Liu, et al., Adv. Synth. Catal. 362 (2020) 2059–2069. doi: 10.1002/adsc.202000151
37. [37]
  K. Xu, Y. Zheng, Y. Ye, D.L. Liu, W.B. Zhang, Org. Lett. 22 (2020) 8836–8841. doi: 10.1021/acs.orglett.0c03211
38. [38]
  K. Xu, H. Liu, Y.L. Hou, et al., Chem. Commun. 55 (2019) 13295–13298. doi: 10.1039/c9cc07204g
39. [39]
  Y. Zheng, S.Q. Dong, K. Xu, D.L. Liu, W.B. Zhang, Org. Lett. 24 (2022) 3440–3444. doi: 10.1021/acs.orglett.2c00937
40. [40]
  Y. Huang, X. Lu, Tetrahedron Lett. 29 (1988) 5663–5664. doi: 10.1016/S0040-4039(00)80839-4
41. [41]
  A.P. Kozikowski, Y. Xia, E.R. Reddy, et al., J. Org. Chem. 56 (1991) 4636–4645. doi: 10.1021/jo00015a014
42. [42]
  S.G. Salamone, G.B. Dudley, Org. Lett. 7 (2005) 4443–4445. doi: 10.1021/ol051730k
43. [43]
  A.J. Grenning, J.H. Boyce, J.A. Porco Jr., J. Am. Chem. Soc. 136 (2014) 11799–11804. doi: 10.1021/ja5060302
44. [44]
  Y. Gai, D. Tang, G. Xu, et al., Bioorg. Med. Chem. Lett. 18 (2008) 6315–6318. doi: 10.1016/j.bmcl.2008.10.109
45. [45]
  R. Ali, S. Anugu, R. Chawla, et al., ACS Omega 4 (2019) 1254–1264. doi: 10.1021/acsomega.8b02555
46. [46]
  H. He, W.B. Liu, L.X. Dai, S.L. You, Angew. Chem. Int. Ed. 49 (2010) 1496–1499. doi: 10.1002/anie.200906638
47. [47]
  K. Ito, Y. Imahayashi, T. Kuroda, et al., Tetrahedron Lett. 45 (2004) 7277–7281. doi: 10.1016/j.tetlet.2004.08.014
48. [48]
  H. Tian, F. Peng, P.X. Zhang, H.J. Yang, H. Fu, Org. Lett. 21 (2019) 8501–8505. doi: 10.1021/acs.orglett.9b03382
49. [49]
  C. Qian, W.J. Tang, Org. Lett. 22 (2020) 4483–4488. doi: 10.1021/acs.orglett.0c01490
50. [50]
  H. Liu, Z.L. Sun, K. Xu, et al., Org. Lett. 22 (2020) 4680–4685. doi: 10.1021/acs.orglett.0c01483
51. [51]
  X. Wang, H.L. Mao, Y.H. Yang, et al., J. Org. Chem. 87 (2022) 15644–15652. doi: 10.1021/acs.joc.2c01873
52. [52]
  Q. Li, K. Yan, Y. Zhu, et al., Chin. Chem. Lett. 34 (2023) 108014. doi: 10.1016/j.cclet.2022.108014
53. [53]
  M.F. Li, S.Q. Shi, T. Xu, et al., Chin. Chem. Lett. 34 (2023) 107751. doi: 10.1016/j.cclet.2022.107751
54. [54]
  F.T. Meng, Y.N. Wang, X.Y. Qin, et al., Nat. Commun. 13 (2022) 7393. doi: 10.1038/s41467-022-35141-4
55. [55]
  J.Y. Wang, C.L. Li, T. Xu, et al., Chin. J. Chem. 40 (2022) 1767–1776. doi: 10.1002/cjoc.202200211
56. [56]
  F.T. Meng, X.Y. Qin, J. Li, et al., Chin. J. Chem. 40 (2022) 687–692. doi: 10.1002/cjoc.202100734
57. [57]
  H.J. Zhang, Z.P. Yang, Q. Gu, S.L. You, Org. Lett. 21 (2019) 3314–3318. doi: 10.1021/acs.orglett.9b01060
58. [58]
  K.N. Zhang, L. Chang, A. Qing, X. Wang, Z.W. Zuo, J. Am. Chem. Soc. 141 (2019) 10556–10564. doi: 10.1021/jacs.9b05932
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