Citation: Ying-Di Hao, Zhi-Qian Lin, Xiao-Yu Guo, Jiao Liang, Can-Kun Luo, Qian-Tao Wang, Li Guo, Yong Wu. Rhodium-catalyzed Doyle-Kirmse rearrangement reactions of sulfoxoniun ylides[J]. Chinese Chemical Letters, ;2024, 35(4): 108834. doi: 10.1016/j.cclet.2023.108834 shu

Rhodium-catalyzed Doyle-Kirmse rearrangement reactions of sulfoxoniun ylides

Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China

wyong@scu.edu.cn

Received Date: 24 April 2023
Revised Date: 1 July 2023
Accepted Date: 23 July 2023
Available Online: 25 July 2023

Figures(6)

Doyle-Kirmse rearrangement reactions have received continuous attention as an important method for constructing complex chemical structures. Herein, we disclosed an efficient rhodium-catalyzed Doyle-Kirmse rearrangement reaction, which can simultaneously construct CC bonds and CX (X = S/Se) bonds using sulfoxonium ylides as starting materials to obtain sulfur- or selenium-containing compounds. This strategy is characterized by the safer and greener carbene precursor, high yields and broad substrate scope, possessing a wide range of application.
- Sulfoxonium ylides,
- Rhodium(II)-catalyzed,
- Carbene,
- Rearrangement reactions,
- One-pot process
1. [1]
  A. Kumar, M.S. Sherikar, V. Hanchate, K.R. Prabhu, Tetrahedron 101 (2021) 132478. doi: 10.1016/j.tet.2021.132478
2. [2]
  A.M. Phelps, V.S. Chan, J.G. Napolitano, et al., J. Org. Chem. 81 (2016) 4158–4169. doi: 10.1021/acs.joc.6b00497
3. [3]
  D. Clare, B.C. Dobson, P.A. Inglesby, C. Aissa, Angew. Chem. Int. Ed. 58 (2019) 16198–16202. doi: 10.1002/anie.201910821
4. [4]
  M. He, Y. Chen, Y. Luo, et al., Green. Synth. Catal. 1 (2020) 180–182. doi: 10.1016/j.gresc.2020.10.004
5. [5]
  W.B. Ma, Y.Q. Tan, Y. Wang, et al., Org. Lett. 23 (2021) 6200–6205. doi: 10.1021/acs.orglett.1c01684
6. [6]
  P.Y. Ushakov, S.L. Loffe, A.Y. Sukhorukov, Org. Chem. Front. 9 (2022) 5358–5382. doi: 10.1039/D2QO00698G
7. [7]
  J.X. Pian, Q.Q. Chen, Y.J. Luo, et al., Org. Lett. 24 (2022) 5641–5645. doi: 10.1021/acs.orglett.2c01724
8. [8]
  D.K. Gopalakrishnan, S. Panigrahi, R. Sen, J. Vaitla, Org. Lett. 25 (2023) 1519–1524. doi: 10.1021/acs.orglett.3c00303
9. [9]
  Y. Zhang, J.B. Wang, Coord. Chem. Rev. 254 (2010) 941–953. doi: 10.1016/j.ccr.2009.12.005
10. [10]
  W. Kirmse, M. Kapps, Chem. Ber. 101 (1968) 994–1003. doi: 10.1002/cber.19681010333
11. [11]
  M.Y. Liao, J.B. Wang, Green Chem. 9 (2007) 184–188. doi: 10.1039/B612743F
12. [12]
  W. Pang, S.F. Zhu, H.F. Jiang, S.Z. Zhu, Tetrahedron 63 (2007) 4543–4547. doi: 10.1016/j.tet.2007.03.050
13. [13]
  R. Hommelsheim, Y.J. Guo, Z. Yang, C. Empel, R.M. Koenigs, Angew. Chem. Int. Ed. 58 (2019) 1203–1207. doi: 10.1002/anie.201811991
14. [14]
  A.K. Steiger, Y. Zhao, M.D. Pluth, Antioxid. Redox Signal. 28 (2018) 1516–1532. doi: 10.1089/ars.2017.7119
15. [15]
  B.L. Oliveira, Z. Guo, G.J.L. Bernardes, Chem. Soc. Rev. 46 (2017) 4895–4950. doi: 10.1039/C7CS00184C
16. [16]
  H. van Goor, J.C. van den Born, J.L. Hillebrands, J.A. Joles, Curr. Opin. Nephrol. Hypertens. 25 (2016) 107–113. doi: 10.1097/MNH.0000000000000206
17. [17]
  Y. Mikhlin, V. Nasluzov, A. Ivaneeva, et al., Mater. Chem. Phys. 255 (2020) 123600. doi: 10.1016/j.matchemphys.2020.123600
18. [18]
  B. Lonnerdal, E. Vargas-Fernandez, M. Whitacre, Food Funct. 8 (2017) 3856–3868. doi: 10.1039/C7FO00746A
19. [19]
  R. Mousa, R.N. Dardashti, N. Metanis, Angew. Chem. Int. Ed. 56 (2017) 15818–15827. doi: 10.1002/anie.201706876
20. [20]
  J. Li, B.X. Shen, S.L. Nie, Z.H. Duan, K.S. Chen, et al., Carbohydr. Polym. 206 (2019) 163–173. doi: 10.1016/j.carbpol.2018.10.088
21. [21]
  N. Bomer, N.G. Beverborg, M.F. Hoes, AA, Eur. J. Heart Fail. 22 (2020) 1415–1423. doi: 10.1002/ejhf.1644
22. [22]
  T. Zhao, J. Zhang, Y.C. Tao, et al., J. Med. Chem. 65 (2022) 4218–4237. doi: 10.1021/acs.jmedchem.1c02057
23. [23]
  S. Miyata, N. Ohhata, H. Murai, et al., J. Antibiot. 45 (1992) 1029–1040. doi: 10.7164/antibiotics.45.1029
24. [24]
  H. Hwang, H. Choi, S.J. Nam, et al., Bull. Korean Chem. Soc. 32 (2011) 4089–4091. doi: 10.5012/bkcs.2011.32.11.4089
25. [25]
  Y.J. Park, M. Koketsu, J.M. Kim, et al., Biol. Pharm. Bull. 26 (2003) 1657–1660. doi: 10.1248/bpb.26.1657
26. [26]
  L. Wu, Z.M. Li, P. Lu, Y.G. Wang, J. Org. Chem. 83 (2018) 13956–13964. doi: 10.1021/acs.joc.8b02307
27. [27]
  M.P. Doyle, W.H. Tamblyn, V. Bagheri, J. Org. Chem. 46 (1981) 5094–5102. doi: 10.1021/jo00338a008
28. [28]
  C.Y. Zhou, W.Y. Yu, P.W.H. Chan, C.M. Che, J. Org. Chem. 69 (2004) 7072–7082. doi: 10.1021/jo049540v
29. [29]
  J.H. Yang, J.Z. Wang, H.T. Huang, et al., Org. Lett. 21 (2019) 2654–2657. doi: 10.1021/acs.orglett.9b00647
30. [30]
  Z.Z. Yu, Y.F. Li, J.M. Shi, et al., Angew. Chem. Int. Ed. 55 (2016) 14807–14811. doi: 10.1002/anie.201608937
31. [31]
  P. Schwab, M.B. France, J.W. Ziller, R.H. Grubbs, Angew. Chem. Int. Ed. 34 (1995) 2039–2041. doi: 10.1002/anie.199520391
32. [32]
  S.F. Zhu, C. Chen, Y. Cai, Q.L. Zhou, Angew. Chem. Int. Ed. 47 (2008) 932–934. doi: 10.1002/anie.200704651
33. [33]
  M. Basato, C. Tubaro, A. Biffis, et al., Chem. Eur. J. 15 (2009) 1516–1526. doi: 10.1002/chem.200801211
34. [34]
  G.K. Murphy, F.Z. Abbas, A.V. Poulton, Adv. Synth. Catal. 356 (2014) 2919–2923. doi: 10.1002/adsc.201400581
35. [35]
  X. Tian, X. Xu, T. Jing, Z. Kang, W. Hu, Green. Synth. Catal. 2 (2021) 337–344. doi: 10.1016/j.gresc.2021.10.007
36. [36]
  X. Zhang, H.X. Huang, X. Guo, et al., Angew. Chem. Int. Ed. 47 (2008) 6647–6649. doi: 10.1002/anie.200801510
37. [37]
  H.Y. Thu, G.S.M. Tong, J.S. Huang, et al., Angew. Chem. Int. Ed. 47 (2008) 9747–9751. doi: 10.1002/anie.200803157
38. [38]
  Z.S. Chen, X.H. Duan, P.X. Zhou, et al., Angew. Chem. Int. Ed. 51 (2012) 1370–1374. doi: 10.1002/anie.201106619
39. [39]
  Y.Z. Zhang, S.F. Zhu, L.X. Wang, Q.L. Zhou, Angew. Chem. Int. Ed. 47 (2008) 8496–8498. doi: 10.1002/anie.200803192
40. [40]
  J.R. Combs, Y.C. Lai, D.L. Van Vranken, Org. Lett. 23 (2021) 2841–2845. doi: 10.1021/acs.orglett.1c00229
41. [41]
  D. Wen, J. Chen, Q. Zheng, S. Yang, T. Tu, CCS Chem. 5 (2023) 1602–1611. doi: 10.31635/ccschem.022.202202233
42. [42]
  C. Qian, Q. Zheng, J. Chen, B. Tu, T. Tu, Green Chem. 25 (2023) 1368–1379. doi: 10.1039/D2GC04195B
43. [43]
  Y.X. Tan, X.Y. Liu, S.Q. Zhang, et al., CCS Chem. 3 (2021) 1582–1595. doi: 10.31635/ccschem.020.202000339
44. [44]
  C.X. Liu, Z.J. Cai, Q. Wang, et al., CCS Chem. 2 (2020) 642–651.
45. [45]
  D. Wang, Y. Zhao, C. Yuan, et al., Angew. Chem. Int. Ed. 58 (2019) 12529– 12533. doi: 10.1002/anie.201906975
46. [46]
  P. Sivaguru, X.H. Bi, Sci. China Chem. 64 (2021) 1614–1629. doi: 10.1007/s11426-021-1052-7
47. [47]
  Y. Kato, K. Miki, F. Nishino, K. Ohe, S. Uemura, Org. Lett. 5 (2003) 2619–2621. doi: 10.1021/ol034731q
48. [48]
  J.L. Li, H. He, M.Y. Huang, et al., Org. Lett. 21 (2019) 9005–9008. doi: 10.1021/acs.orglett.9b03410
49. [49]
  Y.Y. Xu, X. Huang, G.H. Lv, et al., Eur. J. Org. Chem. 2020 (2020) 4635–4638. doi: 10.1002/ejoc.202000716
50. [50]
  H. He, K.C. Yan, J.L. Li, et al., Synthesis-Stuttgart 52 (2020) 3065–3070.
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