Skip to main content
SpringerLink
Log in

N-heterocyclic carbene-catalyzed arene formation reactions

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

Abstract

N-heterocyclic carbene-catalyzed reactions for the formation of aromatic compounds are reviewed. The reactions are subdivided into 4 types based on their activation modes. A brief summary on the achievements and the challenges remaining in N-heterocyclic carbene (NHC)-catalyzed arene construction processes is provided at the end of this review. An outlook into the future research direction within this field is also given based on our own opinion and knowledge on the trends of the development of NHC organocatalysis.

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. van Otterlo WAL, de Koning CB. Chem Rev, 2009, 109: 3743–3782

    Article  CAS  PubMed  Google Scholar 

  2. Domínguez G, Pérez-Castells J. Chem Soc Rev, 2011, 40: 3430–3444

    Article  PubMed  Google Scholar 

  3. Wencel-Delord J, Dröge T, Liu F, Glorius F. Chem Soc Rev, 2011, 40: 4740–4761

    Article  CAS  PubMed  Google Scholar 

  4. Arockiam PB, Bruneau C, Dixneuf PH. Chem Rev, 2012, 112: 5879–5918

    Article  CAS  PubMed  Google Scholar 

  5. Hoye TR, Baire B, Niu D, Willoughby PH, Woods BP. Nature, 2012, 490: 208–212

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Jia Q, Li Y, Lin Y. Chin J Org Chem, 2020, 40: 1502–1513

    Article  CAS  Google Scholar 

  7. Xu K, Wang Z, Zhu T. Synthesis, 2021, 53: 636–652

    Article  CAS  Google Scholar 

  8. Sharique M, Tambar UK. Asian J Org Chem, 2021, 10: 2263–2273

    Article  CAS  Google Scholar 

  9. Enders D, Niemeier O, Henseler A. Chem Rev, 2007, 107: 5606–5655

    Article  CAS  PubMed  Google Scholar 

  10. Biju AT, Kuhl N, Glorius F. Acc Chem Res, 2011, 44: 1182–1195

    Article  CAS  PubMed  Google Scholar 

  11. Bugaut X, Glorius F. Chem Soc Rev, 2012, 41: 3511–3522

    Article  CAS  PubMed  Google Scholar 

  12. Cohen DT, Scheidt KA. Chem Sci, 2012, 3: 53–57

    Article  CAS  PubMed  Google Scholar 

  13. Grossmann A, Enders D. Angew Chem Int Ed, 2012, 51: 314–325

    Article  CAS  Google Scholar 

  14. Ryan SJ, Candish L, Lupton DW. Chem Soc Rev, 2013, 42: 4906–4917

    Article  CAS  PubMed  Google Scholar 

  15. Connon SJ. Angew Chem Int Ed, 2014, 53: 1203–1205

    Article  CAS  Google Scholar 

  16. Hopkinson MN, Richter C, Schedler M, Glorius F. Nature, 2014, 510: 485–496

    Article  CAS  PubMed  Google Scholar 

  17. Mahatthananchai J, Bode JW. Acc Chem Res, 2014, 47: 696–707

    Article  CAS  PubMed  Google Scholar 

  18. Flanigan DM, Romanov-Michailidis F, White NA, Rovis T. Chem Rev, 2015, 115: 9307–9387

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Menon RS, Biju AT, Nair V. Chem Soc Rev, 2015, 44: 5040–5052

    Article  CAS  PubMed  Google Scholar 

  20. Wang MH, Scheidt KA. Angew Chem Int Ed, 2016, 55: 14912–14922

    Article  CAS  Google Scholar 

  21. Chen J, Huang Y. Sci China Chem, 2016, 59: 251–254

    Article  CAS  Google Scholar 

  22. Zhang C, Hooper JF, Lupton DW. ACS Catal, 2017, 7: 2583–2596

    Article  CAS  Google Scholar 

  23. Murauski KJR, Jaworski AA, Scheidt KA. Chem Soc Rev, 2018, 47: 1773–1782

    Article  CAS  PubMed  Google Scholar 

  24. Chen X, Wang H, Jin Z, Chi YR. Chin J Chem, 2020, 38: 1167–1202

    Article  CAS  Google Scholar 

  25. Ghosh A, Biju AT. Angew Chem Int Ed, 2021, 60: 13712–13724

    Article  CAS  Google Scholar 

  26. Chen KQ, Sheng H, Liu Q, Shao PL, Chen XY. Sci China Chem, 2021, 64: 7–16

    Article  CAS  Google Scholar 

  27. Lv J, Xu J, Pan X, Jin Z, Chi YR. Sci China Chem, 2021, 64: 985–990

    Article  CAS  Google Scholar 

  28. Zhao C, Blaszczyk SA, Wang J. Green Synth Catal, 2021, 2: 198–215

    Article  Google Scholar 

  29. Yang X, Wang H, Jin Z, Chi YR. Green Synth Catal, 2021, 2: 295–298

    Article  Google Scholar 

  30. Zhu T, Zheng P, Mou C, Yang S, Song BA, Chi YR. Nat Commun, 2014, 5: 5027

    Article  CAS  PubMed  Google Scholar 

  31. Ni Z, Mou C, Zhu X, Qi P, Yang S, Chi YR, Jin Z. Eur J Org Chem, 2020, 2020(4): 492–495

    Article  CAS  Google Scholar 

  32. Hao L, Du Y, Lv H, Chen X, Jiang H, Shao Y, Chi YR. Org Lett, 2012, 14: 2154–2157

    Article  CAS  PubMed  Google Scholar 

  33. Wu J, Mou C, Chi YR. Chin J Chem, 2018, 36: 333–337

    Article  CAS  Google Scholar 

  34. Zhu T, Liu Y, Smetankova M, Zhuo S, Mou C, Chai H, Jin Z, Chi YR. Angew Chem Int Ed, 2019, 58: 15778–15782

    Article  CAS  Google Scholar 

  35. Hu JM, Zhang JQ, Sun BB, Chen JB, Yu JQ, Yang XP, Lv HP, Wang Z, Wang XW. Org Lett, 2019, 21: 8582–8586

    Article  CAS  PubMed  Google Scholar 

  36. Chen KQ, Luo Z, Gao ZH, Ye S. Chem Eur J, 2019, chem.201806225

  37. Huang X, Zhu T, Huang Z, Zhang Y, Jin Z, Zanoni G, Chi YR. Org Lett, 2017, 19: 6188–6191

    Article  CAS  PubMed  Google Scholar 

  38. Zhu T, Mou C, Li B, Smetankova M, Song BA, Chi YR. J Am Chem Soc, 2015, 137: 5658–5661

    Article  CAS  PubMed  Google Scholar 

  39. Xu K, Li W, Zhu S, Zhu T. Angew Chem Int Ed, 2019, 58: 17625–17630

    Article  CAS  Google Scholar 

  40. Mondal S, Yetra SR, Mukherjee S, Biju AT. Acc Chem Res, 2019, 52: 425–436

    Article  CAS  PubMed  Google Scholar 

  41. Jia Q, Wang J. Org Lett, 2016, 18: 2212–2215

    Article  CAS  PubMed  Google Scholar 

  42. Zhang CL, Gao ZH, Liang ZQ, Ye S. Adv Synth Catal, 2016, 358: 2862–2866

    Article  CAS  Google Scholar 

  43. Zhang CL, Ye S. Org Lett, 2016, 18: 6408–6411

    Article  CAS  PubMed  Google Scholar 

  44. Liu D, Gao Y, Huang J, Fu Z, Huang W. J Org Chem, 2018, 83: 14210–14217

    Article  CAS  PubMed  Google Scholar 

  45. Zhang C, Gao Y, Wang H, Zhou B, Ye S. Angew Chem Int Ed, 2021, 60: 13918–13922

    Article  CAS  Google Scholar 

  46. Candish L, Levens A, Lupton DW. Chem Sci, 2015, 6: 2366–2370

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  47. Mou C, Wu J, Huang Z, Sun J, Jin Z, Chi YR. Chem Commun, 2017, 53: 13359–13362

    Article  CAS  Google Scholar 

  48. Ma R, Wang X, Zhang Q, Chen L, Gao J, Feng J, Wei D, Du D. Org Lett, 2021, 23: 4267–4272

    Article  CAS  PubMed  Google Scholar 

  49. Bugaut X, Glorius F. Chem Soc Rev, 2012, 41: 3511–3522

    Article  CAS  PubMed  Google Scholar 

  50. Yetra S, Patra A, Biju A. Synthesis, 2015, 47: 1357–1378

    Article  CAS  Google Scholar 

  51. Menon RS, Biju AT, Nair V. Beilstein J Org Chem, 2016, 12: 444–461

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  52. Liu P, Lei M, Ma L, Hu L. Synlett, 2011, 2011(8): 1133–1136

    Article  Google Scholar 

  53. Yu C, Lu J, Li T, Wang D, Qin B, Zhang H, Yao C. Synlett, 2011, 2011 (16): 2420–2424

    Article  Google Scholar 

  54. Sharique M, Tambar UK. Chem Sci, 2020, 11: 7239–7243

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  55. Nakano Y, Lupton DW. Angew Chem Int Ed, 2016, 55: 3135–3139

    Article  CAS  Google Scholar 

  56. Patra A, Mukherjee S, Das TK, Jain S, Gonnade RG, Biju AT. Angew Chem Int Ed, 2017, 56: 2730–2734

    Article  CAS  Google Scholar 

  57. Harish B, Subbireddy M, Suresh S. Chem Commun, 2017, 53: 3338–3341

    Article  CAS  Google Scholar 

  58. Patra A, Gelat F, Pannecoucke X, Poisson T, Besset T, Biju AT. Org Lett, 2018, 20: 1086–1089

    Article  CAS  PubMed  Google Scholar 

  59. Hao L, Chuen CW, Ganguly R, Chi YR. Synlett, 2013, 24: 1197–1120

    Article  CAS  Google Scholar 

  60. Kong X, Zhang G, Yang S, Liu X, Fang X. Adv Synth Catal, 2017, 359: 2729–2734

    Article  CAS  Google Scholar 

  61. Liu J, Das DK, Zhang G, Yang S, Zhang H, Fang X. Org Lett, 2018, 20: 64–67

    Article  CAS  PubMed  Google Scholar 

  62. Lu X, Zhang C, Xu Z. Acc Chem Res, 2001, 34: 535–544

    Article  CAS  PubMed  Google Scholar 

  63. Yu S, Ma S. Angew Chem Int Ed, 2012, 51: 3074–3112

    Article  CAS  Google Scholar 

  64. Wang T, Han X, Zhong F, Yao W, Lu Y. Acc Chem Res, 2016, 49: 1369–1378

    Article  CAS  PubMed  Google Scholar 

  65. Sun L, Wang T, Ye S. Chin J Chem, 2012, 30: 190–194

    Article  CAS  Google Scholar 

  66. Li S, Tang Z, Wang Y, Wang D, Wang Z, Yu C, Li T, Wei D, Yao C. Org Lett, 2019, 21: 1306–1310

    Article  CAS  PubMed  Google Scholar 

  67. Wu W, Xu S, Zhang Y, Wang X, Li R, Sun F, Yu C, Li T, Wei D, Yao C. Org Chem Front, 2020, 7: 1593–1599

    Article  CAS  Google Scholar 

  68. Zhou P, Wang JY, Zhang TS, Li G, Hao WJ, Tu SJ, Jiang B. Chem Commun, 2017, 54: 164–167

    Article  Google Scholar 

  69. Ma D, Fu C, Ma S. Chem Commun, 2016, 52: 14426–14429

    Article  CAS  Google Scholar 

  70. Lopez SS, Jaworski AA, Scheidt KA. J Org Chem, 2018, 83: 14637–14645

    Article  CAS  PubMed  Google Scholar 

  71. Xie Y, Yang X, Xu J, Chai H, Liu H, Zhang J, Song J, Gao Y, Jin Z, Chi YR. Angew Chem Int Ed, 2021, 60: 14817–14823

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang, 550025, China

    Tingting Li, Zhichao Jin & Yonggui Robin Chi

  2. Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore

    Yonggui Robin Chi

Authors
  1. Tingting Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zhichao Jin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yonggui Robin Chi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yonggui Robin Chi.

Additional information

Conflict of interest

The authors declare 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

Li, T., Jin, Z. & Chi, Y.R. N-heterocyclic carbene-catalyzed arene formation reactions. Sci. China Chem. 65, 210–223 (2022). https://doi.org/10.1007/s11426-021-1133-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-021-1133-5

Search

Navigation