Science China Chemistry

, Volume 62, Issue 11, pp 1463–1475 | Cite as

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

  • Chong-Hui Xu
  • Yang Li
  • Jin-Heng LiEmail author
  • Jian-Nan Xiang
  • Wei DengEmail author


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.


radical annulation oxidants 1,n-enynes polycycles 


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

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


  1. 1(a).
    Paquette LA. Comprehensive Organic Synthesis. Vol. 5. Oxford, New York, Seoul, Tokyo: Pergamon, 1991Google Scholar
  2. 1(b).
    Taylor RD, MacCoss M, Lawson ADG. J Med Chem, 2014, 57: 5845–5859PubMedGoogle Scholar
  3. 1(c).
    Hammer N, Leth LA, Stiller J, Jensen ME, Jørgensen KA. Chem Sci, 2016, 7: 3649–3657PubMedPubMedCentralGoogle Scholar
  4. 2(a).
    Ye LW, Zhou J, Tang Y. Chem Soc Rev, 2008, 37: 1140–1152PubMedGoogle Scholar
  5. 2(b).
    Inglesby PA, Evans PA. Chem Soc Rev, 2010, 39: 2791–2805PubMedGoogle Scholar
  6. 2(c).
    Kotha S, Lahiri K. Synlett, 2007, 2007(18): 2767–2784Google Scholar
  7. 2(d).
    Wu P, Nielsen TE. Chem Rev, 2017, 117: 7811–7856PubMedGoogle Scholar
  8. 3(a).
    Lu LQ, Chen JR, Xiao WJ. Acc Chem Res, 2012, 45: 1278–1293PubMedGoogle Scholar
  9. 3(b).
    Xu PF, Wang W. Catalytic Cascade Reactions. Hoboken: Wiley, 2014Google Scholar
  10. 3(c).
    Song RJ, Liu Y, Xie YX, Li JH. Synthesis, 2015, 47: 1195–1209Google Scholar
  11. 3(d).
    Xuan J, Studer A. Chem Soc Rev, 2017, 46: 4329–4346PubMedGoogle Scholar
  12. 4(a).
    Aubert C, Buisine O, Malacria M. Chem Rev, 2002, 102: 813–834PubMedGoogle Scholar
  13. 4(b).
    Michelet V, Toullec PY, Genêt JP. Angew Chem Int Ed, 2008, 47: 4268–4315Google Scholar
  14. 4(c).
    Zhang DH, Zhang Z, Shi M. Chem Commun, 2012, 48: 10271–10279Google Scholar
  15. 4(d).
    Huang MH, Hao WJ, Jiang B. Chem Asian J, 2018, 13: 2958–2977PubMedGoogle Scholar
  16. 5.
    Hu M, Fan JH, Liu Y, Ouyang XH, Song RJ, Li JH. Angew Chem Int Ed, 2015, 54: 9577–9580Google Scholar
  17. 6.
    Qiu JK, Jiang B, Zhu YL, Hao WJ, Wang DC, Sun J, Wei P, Tu SJ, Li G. J Am Chem Soc, 2015, 137: 8928–8931PubMedGoogle Scholar
  18. 7.
    Hu M, Zou HX, Song RJ, Xiang JN, Li JH. Org Lett, 2016, 18: 6460–6463PubMedGoogle Scholar
  19. 8.
    Hu M, Li M, Tan FL, Song RJ, Xie YX, Li JH. Adv Synth Catal, 2017, 359: 120–129Google Scholar
  20. 9.
    Jiang B, Li J, Pan Y, Hao W, Li G, Tu S. Chin J Chem, 2017, 35: 323–334Google Scholar
  21. 10(a).
    Ouyang XH, Song RJ, Li JH. Chem Asian J, 2018, 13: 2316–2332PubMedGoogle Scholar
  22. 10(b).
    Hu M, Song RJ, Ouyang XH, Tan FL, Wei WT, Li JH. Chem Commun, 2016, 52: 3328–3331Google Scholar
  23. 11.
    Li Y, Liu B, Song RJ, Wang QA, Li JH. Adv Synth Catal, 2016, 358: 1219–1228Google Scholar
  24. 12.
    Gao F, Yang C, Ma N, Gao GL, Li D, Xia W. Org Lett, 2016, 18: 600–603PubMedGoogle Scholar
  25. 13.
    Tan FL, Hu M, Song RJ, Li JH. Adv Synth Catal, 2017, 359: 3602–3610Google Scholar
  26. 14(a).
    Lv L, Li Z. J Org Chem, 2017, 82: 2689–2702PubMedGoogle Scholar
  27. 14(b).
    Li J, Hao WJ, Zhou P, Zhu YL, Wang SL, Tu SJ, Jiang B. RSC Adv, 2017, 7: 9693–9703Google Scholar
  28. 15.
    Li J, Zhang WW, Wei XJ, Liu F, Hao WJ, Wang SL, Li G, Tu SJ, Jiang B. J Org Chem, 2017, 82: 6621–6628PubMedGoogle Scholar
  29. 16.
    Wang Q, Song H, Liu Y, Song H, Wang Q. Adv Synth Catal, 2016, 358: 3435–3442Google Scholar
  30. 17.
    Liu Y, Zhang JL, Song RJ, Qian PC, Li JH. Angew Chem Int Ed, 2014, 53: 9017–9020Google Scholar
  31. 18.
    Ouyang XH, Song RJ, Liu Y, Hu M, Li JH. Org Lett, 2015, 17: 6038–6041PubMedGoogle Scholar
  32. 19.
    Zhao Y, Hu Y, Wang H, Li X, Wan B. J Org Chem, 2016, 81: 4412–4420PubMedGoogle Scholar
  33. 20.
    Liu Y, Zhang JL, Song RJ, Li JH. Org Lett, 2014, 16: 5838–5841PubMedGoogle Scholar
  34. 21(a).
    Yu JX, Niu S, Hu M, Xiang JN, Li JH. Chem Commun, 2019, 55: 6727–6730Google Scholar
  35. 21(b).
    Qin JH, Yu JX, Li JH, An DL. Adv Synth Catal, 2019, 361: 3974–3979Google Scholar
  36. 22.
    Huang MH, Zhu YL, Hao WJ, Wang AF, Wang DC, Liu F, Wei P, Tu SJ, Jiang B. Adv Synth Catal, 2017, 359: 2229–2234Google Scholar
  37. 23.
    Deng GB, Wang ZQ, Xia JD, Qian PC, Song RJ, Hu M, Gong LB, Li JH. Angew Chem Int Ed, 2013, 52: 1535–1538Google Scholar
  38. 24.
    Liu Y, Zhang JL, Zhou MB, Song RJ, Li JH. Chem Commun, 2014, 50: 14412–14414Google Scholar
  39. 25.
    Zhu YL, Jiang B, Hao WJ, Qiu JK, Sun J, Wang DC, Wei P, Wang AF, Li G, Tu SJ. Org Lett, 2015, 17: 6078–6081PubMedGoogle Scholar
  40. 26.
    An Y, Zhang J, Xia H, Wu J. Org Chem Front, 2017, 4: 1318–1321Google Scholar
  41. 27.
    Xuan J, Gonzalez-Abradelo D, Strassert CA, Daniliuc CG, Studer A. Eur J Org Chem, 2016, 2016(29): 4961–4964Google Scholar
  42. 28.
    Xuan J, Daniliuc CG, Studer A. Org Lett, 2016, 18: 6372–6375PubMedPubMedCentralGoogle Scholar
  43. 29.
    Li Y, Pan GH, Hu M, Liu B, Song RJ, Li JH. Chem Sci, 2016, 7: 7050–7054PubMedPubMedCentralGoogle Scholar
  44. 30.
    Lv L, Bai X, Yan X, Li Z. Org Chem Front, 2016, 3: 1509–1513Google Scholar
  45. 31.
    Liu B, Wang CY, Hu M, Song RJ, Chen F, Li JH. Chem Commun, 2017, 53: 1265–1268Google Scholar
  46. 32.
    Lv L, Li Z. Org Lett, 2016, 18: 2264–2267PubMedGoogle Scholar
  47. 33.
    Li CG, Xu GQ, Xu PF. Org Lett, 2017, 19: 512–515PubMedGoogle Scholar
  48. 34.
    Yang Y, Song RJ, Li Y, Ouyang XH, Li JH, He DL. Chem Commun, 2018, 54: 1441–1444Google Scholar

Copyright information

© Science China Press and Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical EngineeringHunan UniversityChangshaChina
  2. 2.Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources RecycleNanchang Hangkong UniversityNanchangChina

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