Skip to main content
SpringerLink
Log in

Recent advances in radical-mediated [2+2+m] annulation of 1,n-enynes

  • Reviews
  • Published:
Science China Chemistry Aims and scope Submit manuscript

Abstract

1,n-Enynes are a versatile class of unsaturated hydrocarbons that find broad applications in the synthetic community of natural products, biologically active structures and functional materials. Typical methods for the transformations of 1,n-enynes include the radical-mediated [2+2+m] annulation reaction as they are particularly efficient accesses to functionalized polycyclic compounds. We herein highlighted recent process in the radical-mediated [2+2+m] annulation of 1,n-enynes, including [2+2+1] and [2+2+2] modes, for the construction of five- to six-membered-ring-fused polycyclic scaffolds. Meanwhile, the mechanisms for these transformations were described.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Paquette LA. Comprehensive Organic Synthesis. Vol. 5. Oxford, New York, Seoul, Tokyo: Pergamon, 1991

    Google Scholar 

  2. Taylor RD, MacCoss M, Lawson ADG. J Med Chem, 2014, 57: 5845–5859

    CAS  PubMed  Google Scholar 

  3. Hammer N, Leth LA, Stiller J, Jensen ME, Jørgensen KA. Chem Sci, 2016, 7: 3649–3657

    CAS  PubMed  PubMed Central  Google Scholar 

  4. Ye LW, Zhou J, Tang Y. Chem Soc Rev, 2008, 37: 1140–1152

    CAS  PubMed  Google Scholar 

  5. Inglesby PA, Evans PA. Chem Soc Rev, 2010, 39: 2791–2805

    CAS  PubMed  Google Scholar 

  6. Kotha S, Lahiri K. Synlett, 2007, 2007(18): 2767–2784

    Google Scholar 

  7. Wu P, Nielsen TE. Chem Rev, 2017, 117: 7811–7856

    CAS  PubMed  Google Scholar 

  8. Lu LQ, Chen JR, Xiao WJ. Acc Chem Res, 2012, 45: 1278–1293

    CAS  PubMed  Google Scholar 

  9. Xu PF, Wang W. Catalytic Cascade Reactions. Hoboken: Wiley, 2014

    Google Scholar 

  10. Song RJ, Liu Y, Xie YX, Li JH. Synthesis, 2015, 47: 1195–1209

    CAS  Google Scholar 

  11. Xuan J, Studer A. Chem Soc Rev, 2017, 46: 4329–4346

    CAS  PubMed  Google Scholar 

  12. Aubert C, Buisine O, Malacria M. Chem Rev, 2002, 102: 813–834

    CAS  PubMed  Google Scholar 

  13. Michelet V, Toullec PY, Genêt JP. Angew Chem Int Ed, 2008, 47: 4268–4315

    CAS  Google Scholar 

  14. Zhang DH, Zhang Z, Shi M. Chem Commun, 2012, 48: 10271–10279

    CAS  Google Scholar 

  15. Huang MH, Hao WJ, Jiang B. Chem Asian J, 2018, 13: 2958–2977

    CAS  PubMed  Google Scholar 

  16. Hu M, Fan JH, Liu Y, Ouyang XH, Song RJ, Li JH. Angew Chem Int Ed, 2015, 54: 9577–9580

    CAS  Google Scholar 

  17. Qiu JK, Jiang B, Zhu YL, Hao WJ, Wang DC, Sun J, Wei P, Tu SJ, Li G. J Am Chem Soc, 2015, 137: 8928–8931

    CAS  PubMed  Google Scholar 

  18. Hu M, Zou HX, Song RJ, Xiang JN, Li JH. Org Lett, 2016, 18: 6460–6463

    CAS  PubMed  Google Scholar 

  19. Hu M, Li M, Tan FL, Song RJ, Xie YX, Li JH. Adv Synth Catal, 2017, 359: 120–129

    CAS  Google Scholar 

  20. Jiang B, Li J, Pan Y, Hao W, Li G, Tu S. Chin J Chem, 2017, 35: 323–334

    CAS  Google Scholar 

  21. Ouyang XH, Song RJ, Li JH. Chem Asian J, 2018, 13: 2316–2332

    CAS  PubMed  Google Scholar 

  22. Hu M, Song RJ, Ouyang XH, Tan FL, Wei WT, Li JH. Chem Commun, 2016, 52: 3328–3331

    CAS  Google Scholar 

  23. Li Y, Liu B, Song RJ, Wang QA, Li JH. Adv Synth Catal, 2016, 358: 1219–1228

    CAS  Google Scholar 

  24. Gao F, Yang C, Ma N, Gao GL, Li D, Xia W. Org Lett, 2016, 18: 600–603

    CAS  PubMed  Google Scholar 

  25. Tan FL, Hu M, Song RJ, Li JH. Adv Synth Catal, 2017, 359: 3602–3610

    CAS  Google Scholar 

  26. Lv L, Li Z. J Org Chem, 2017, 82: 2689–2702

    CAS  PubMed  Google Scholar 

  27. Li J, Hao WJ, Zhou P, Zhu YL, Wang SL, Tu SJ, Jiang B. RSC Adv, 2017, 7: 9693–9703

    CAS  Google Scholar 

  28. Li J, Zhang WW, Wei XJ, Liu F, Hao WJ, Wang SL, Li G, Tu SJ, Jiang B. J Org Chem, 2017, 82: 6621–6628

    CAS  PubMed  Google Scholar 

  29. Wang Q, Song H, Liu Y, Song H, Wang Q. Adv Synth Catal, 2016, 358: 3435–3442

    CAS  Google Scholar 

  30. Liu Y, Zhang JL, Song RJ, Qian PC, Li JH. Angew Chem Int Ed, 2014, 53: 9017–9020

    CAS  Google Scholar 

  31. Ouyang XH, Song RJ, Liu Y, Hu M, Li JH. Org Lett, 2015, 17: 6038–6041

    CAS  PubMed  Google Scholar 

  32. Zhao Y, Hu Y, Wang H, Li X, Wan B. J Org Chem, 2016, 81: 4412–4420

    CAS  PubMed  Google Scholar 

  33. Liu Y, Zhang JL, Song RJ, Li JH. Org Lett, 2014, 16: 5838–5841

    CAS  PubMed  Google Scholar 

  34. Yu JX, Niu S, Hu M, Xiang JN, Li JH. Chem Commun, 2019, 55: 6727–6730

    CAS  Google Scholar 

  35. Qin JH, Yu JX, Li JH, An DL. Adv Synth Catal, 2019, 361: 3974–3979

    CAS  Google Scholar 

  36. Huang MH, Zhu YL, Hao WJ, Wang AF, Wang DC, Liu F, Wei P, Tu SJ, Jiang B. Adv Synth Catal, 2017, 359: 2229–2234

    CAS  Google Scholar 

  37. Deng GB, Wang ZQ, Xia JD, Qian PC, Song RJ, Hu M, Gong LB, Li JH. Angew Chem Int Ed, 2013, 52: 1535–1538

    CAS  Google Scholar 

  38. Liu Y, Zhang JL, Zhou MB, Song RJ, Li JH. Chem Commun, 2014, 50: 14412–14414

    CAS  Google Scholar 

  39. Zhu YL, Jiang B, Hao WJ, Qiu JK, Sun J, Wang DC, Wei P, Wang AF, Li G, Tu SJ. Org Lett, 2015, 17: 6078–6081

    CAS  PubMed  Google Scholar 

  40. An Y, Zhang J, Xia H, Wu J. Org Chem Front, 2017, 4: 1318–1321

    CAS  Google Scholar 

  41. Xuan J, Gonzalez-Abradelo D, Strassert CA, Daniliuc CG, Studer A. Eur J Org Chem, 2016, 2016(29): 4961–4964

    CAS  Google Scholar 

  42. Xuan J, Daniliuc CG, Studer A. Org Lett, 2016, 18: 6372–6375

    CAS  PubMed  PubMed Central  Google Scholar 

  43. Li Y, Pan GH, Hu M, Liu B, Song RJ, Li JH. Chem Sci, 2016, 7: 7050–7054

    CAS  PubMed  PubMed Central  Google Scholar 

  44. Lv L, Bai X, Yan X, Li Z. Org Chem Front, 2016, 3: 1509–1513

    CAS  Google Scholar 

  45. Liu B, Wang CY, Hu M, Song RJ, Chen F, Li JH. Chem Commun, 2017, 53: 1265–1268

    CAS  Google Scholar 

  46. Lv L, Li Z. Org Lett, 2016, 18: 2264–2267

    CAS  PubMed  Google Scholar 

  47. Li CG, Xu GQ, Xu PF. Org Lett, 2017, 19: 512–515

    CAS  PubMed  Google Scholar 

  48. Yang Y, Song RJ, Li Y, Ouyang XH, Li JH, He DL. Chem Commun, 2018, 54: 1441–1444

    CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (21625203, 21871126) and the Jiangxi Province Science and Technology Project (20182BCB22007).

Author information

Authors and Affiliations

  1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, China

    Chong-Hui Xu, Jin-Heng Li, Jian-Nan Xiang & Wei Deng

  2. Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang, 330063, China

    Chong-Hui Xu, Yang Li & Jin-Heng Li

Authors
  1. Chong-Hui Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yang Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jin-Heng Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jian-Nan Xiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Wei Deng
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Jin-Heng Li or Wei Deng.

Ethics declarations

Conflict of interest The authors declare that they have no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Xu, CH., Li, Y., Li, JH. et al. Recent advances in radical-mediated [2+2+m] annulation of 1,n-enynes. Sci. China Chem. 62, 1463–1475 (2019). https://doi.org/10.1007/s11426-019-9615-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-019-9615-0

Keywords

Search

Navigation