Skip to main content
SpringerLink
Log in

Recent Advances in C-O Bond Construction via C-H Activation

  • Review
  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

An Erratum to this article was published on 01 June 2019

This article has been updated

Abstract

The direct construction of C-O bond by C-H activation is a highly efficient and practical method for the synthesis of esters, ethers, and hydroxy compounds. As compared to the conventional method of mutual functional group conversion, the C-H activation method provides not only improved atomic economy and reduced number of synthetic steps but also greatly improved overall yield of multistep syntheses. Studies of C-H activation to construct C-O bonds are crucial in the field of organic synthesis and catalysis research, and they have already been one of the research hotspots in related fields. According to the current trends in the development of C-H activation, different reaction types and different reaction conditions are classified in this review, and the latest advances in C-H activation to form C-O bonds are discussed.

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

Change history

  • 30 July 2019

    The second author should be Chen-Fu Liu.

References

  1. Demir, A.S. and Emrullahoglu, M., Curr. Org. Synth., 2007, vol. 4, p. 321.

    Article  CAS  Google Scholar 

  2. Gol’dshleger, N.F., Es’kova, V.V., Shilov, A.E., and Shteinman, A.A., Zh. Fiz. Khim., 1972, vol. 46, p. 1353.

    Google Scholar 

  3. Haines, B.E. and Musaev, D.G., ACS Catal., 2015, vol. 5, p. 830.

    Article  CAS  Google Scholar 

  4. Chen, Z., Wang, B., Zhang, J., Yu, W., Liu, Z., and Zhang, Y., Org. Chem. Front., 2015, vol. 2, p. 1107.

    Article  CAS  Google Scholar 

  5. Shi, H., Babinski, D.J., and Ritter, T., J. Am. Chem. Soc., 2015, vol. 137, p. 3775.

    Article  CAS  PubMed  Google Scholar 

  6. Dai, H.X., Li, G., Zhang, X.G., Stepan, A.F., and Yu, J. Q., J. Am. Chem. Soc., 2013, vol. 135, p. 7567.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Díaz-Requejo, M.M. and Pérez, P.J., Chem. Rev., 2008, vol. 108, p. 3379.

    Article  CAS  PubMed  Google Scholar 

  8. Lyons, T.W. and Sanford, M.S., Chem. Rev., 2010, vol. 110, p. 1147.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Guo, X.X., Gu, D.W., Wu, Z., and Zhang, W., Chem. Rev., 2015, vol. 115, p. 1622.

    Article  CAS  PubMed  Google Scholar 

  10. Krylov, I.B., Vil’, VA., and Terent’ev, A.O., Beilstein J. Org. Chem., 2015, vol. 11, p. 92.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Labinger, J.A., Chem. Rev., 2017, vol. 117, p. 8483.

    Article  CAS  PubMed  Google Scholar 

  12. Dick, A.R., Hull, K.L., and Sanford, M.S., J. Am. Chem. Soc., 2004, vol. 126, p. 2300.

    Article  CAS  PubMed  Google Scholar 

  13. Kalyani, D. and Sanford, M.S., Org. Lett., 2005, vol. 7, p. 4149.

    Article  CAS  PubMed  Google Scholar 

  14. Racowski, J.M., Dick, A.R., and Sanford, M.S., J. Am. Chem. Soc., 2009, vol. 131, p. 10974.

    Article  CAS  PubMed  Google Scholar 

  15. Fu, X., Wei, Z., Xia, C., Shen, C., Xu, J., Yang, Y., Wang, K., and Zhang, P., Catal. Lett., 2017, vol. 147, p. 400.

    Article  CAS  Google Scholar 

  16. Qian, C., Lin, D., Deng, Y., Zhang, X.Q., Jiang, H., Miao, G., Tang, X., and Zeng, W., Org. Biomol. Chem., 2014, vol. 12, p. 5866.

    Article  CAS  PubMed  Google Scholar 

  17. Litman, Z.C., Sharma, A., and Hartwig, J.F., ACS Catal., 2017, vol. 7, p. 1998.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Guo, Y., Xiang, Y., Wei, L., and Wan, J.P., Org. Lett., 2018, vol. 20, p. 3971.

    Article  CAS  PubMed  Google Scholar 

  19. Zhao, J., Fang, H., Zhou, W., Han, J., and Pan, Y., J. Org. Chem., 2014, vol. 79, p. 3847.

    Article  CAS  PubMed  Google Scholar 

  20. Zhang, D., Cui, X., Yang, F., Zhang, Q., Zhua, Y., and Wu, Y., Org. Chem. Front., 2015, vol. 2, p. 951.

    Article  CAS  Google Scholar 

  21. Xia, C., Wang, K., Xu, J., Shen, C., Sun, D., Li, H., Wang, G., and Zhang, P., Org. Biomol. Chem., 2017, vol. 15, p. 531.

    Article  CAS  PubMed  Google Scholar 

  22. Wang, F., Hu, Q., Shu, C., Lin, Z., Min, D., Shi, T., and Zhang, W., Org. Lett., 2017, vol. 19, p. 3636.

    Article  CAS  PubMed  Google Scholar 

  23. Matsumoto, K., Tachikawa, S., Hashimoto, N., Nakano, R., Yoshida, M., and Shindo, M., J. Org. Chem., 2017, vol. 82, p. 4305.

    Article  CAS  PubMed  Google Scholar 

  24. Ren, T.L., Xu, B.H., Mahmood, S., Sun, M.X., and Zhang, S.J., Tetrahedron, 2017, vol. 73, p. 2943.

    Article  CAS  Google Scholar 

  25. Yin, Z., Jiang, X., and Sun, P., J. Org. Chem., 2013, vol. 78, p. 10002.

    Article  CAS  PubMed  Google Scholar 

  26. Shi, S. and Kuang, C., J. Org. Chem., 2014, vol. 79, p. 6105.

    Article  CAS  PubMed  Google Scholar 

  27. Péron, F., Fossey, C., Santos, J.S.O., Cailly, T., and Fabis, F., Chem. Eur. J., 2014, vol. 20, p. 1.

    Article  CAS  Google Scholar 

  28. Yang, L., Li, S., Cai, L., Ding, Y., Fu, L., Cai, Z., Ji, H., and Li, G., Org. Lett., 2017, vol. 19, p. 2746.

    Article  CAS  PubMed  Google Scholar 

  29. Takemura, N., Kuninobu, Y., and Kanai, M., Org. Lett., 2013, vol. 15, p. 844.

    Article  CAS  PubMed  Google Scholar 

  30. Zhang, L.B., Hao, X.Q., Zhang, S.K., Liu, K., Ren, B., Gong, J.F., Niu, J.L., and Song, M.P., J. Org. Chem., 2014, vol. 79, p. 10399.

    Article  CAS  PubMed  Google Scholar 

  31. Liu, Z., Huang, F., Lou, J., Wang, Q., and Yu, Z., Org. Biomol. Chem., 2017, vol. 15, p. 5535.

    Article  CAS  PubMed  Google Scholar 

  32. Lu, W., Xu, H., and Shen, Z., Org. Biomol. Chem., 2017, vol. 15, p. 1261.

    Article  CAS  PubMed  Google Scholar 

  33. Zheng, Y.W., Ye, P., Chen, B., Meng, Q.Y., Feng, K., Wang, W., Wu, L.Z., and Tung, C.H., Org. Lett., 2017, vol. 19, p. 2206.

    Article  CAS  PubMed  Google Scholar 

  34. Zhang, G., Zhu, J., and Ding, C., ChemistrySelect, 2018, vol. 3, p. 9803.

    Article  CAS  Google Scholar 

  35. Liu, S.K., Cui, X.F., Liu, X.X., Ma, H.J., Wei, D.D., Luo, X.L., and Huang, G.S., ChemistrySelect, 2018, vol. 3, p. 3989.

    Article  CAS  Google Scholar 

  36. Han, J.N., Du, C., Zhu, X., Wang, Z.L., Zhu, Y., Chu, Z.Y., Niu, J.L., and Song, M.P., Beilstein J. Org. Chem., 2018, vol. 14, p. 2090.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  37. Jiang, Q., Wang, J.Y., and Guo, C., J. Org. Chem., 2014, vol. 79, p. 8768.

    Article  CAS  PubMed  Google Scholar 

  38. Kibriya, G., Samanta, S., Jana, S., Mondal, S., and Hajra, A., J. Org. Chem., 2017, vol. 82, p. 13 722.

    Article  CAS  Google Scholar 

  39. Sun, S.Z., Shang, M., Wang, H.L., Lin, H.X., Dai, H.X., and Yu, J.Q., J. Org. Chem., 2015, vol. 80, p. 8843.

    Article  CAS  PubMed  Google Scholar 

  40. Das, P., Saha, D., Saha, D., and Guin, J., ACS Catal., 2016, vol. 6, p. 6050.

    Article  CAS  Google Scholar 

  41. Sheng, X., Zhang, J., Yang, H., and Jiang, G., Org. Lett., 2017, vol. 19, p. 2618.

    Article  CAS  PubMed  Google Scholar 

  42. Chaudhari, M.B., Sutar, Y., Malpathak, S., Hazra, A., and Gnanaprakasam, B., Org. Lett., 2017, vol. 19, p. 3628.

    Article  CAS  PubMed  Google Scholar 

  43. Das, P. and Guin, J., ChemCatChem, 2018, vol. 10, p. 2370.

    Article  CAS  Google Scholar 

  44. Pierce, C.J. and Hilinski, M.K., Org. Lett., 2014, vol. 16, p. 6504.

    Article  CAS  PubMed  Google Scholar 

  45. Yamaguchi, T., Yamaguchi, E., Tada, N., and Itoh, A., Adv. Synth. Catal., 2015, vol. 357, p. 2017.

    Article  CAS  Google Scholar 

  46. Dong, J., Liu, P., and Sun, P., J. Org. Chem., 2015, vol. 80, p. 2925.

    Article  CAS  PubMed  Google Scholar 

  47. Liang, Y.F., Wang, X., Yuan, Y., Liang, Y., Li, X., and Jiao, N., ACS Catal., 2015, vol. 5, p. 6148.

    Article  CAS  Google Scholar 

  48. Shuler, W.G., Johnson, S.L., and Hilinski, M.K., Org. Lett., 2017, vol. 19, p. 4790.

    Article  CAS  PubMed  Google Scholar 

  49. Kim, K., Hyun, J., Kim, J., and Kim, H., Asian J. Org. Chem., 2017, vol. 6, p. 907.

    Article  CAS  Google Scholar 

  50. Chen, X.Y., Ozturk, S., and Sorensen, E.J., Org. Lett., 2017, vol. 19, p. 6280.

    Article  CAS  PubMed  Google Scholar 

  51. Mack, J.B.C., Gipson, J.D., Du Bois, J., and Sigman, M.S., J. Am. Chem. Soc., 2017, vol. 139, p. 9503.

    Article  CAS  PubMed  Google Scholar 

  52. Li, G.X., Morales-Rivera, C.A., Gao, F., Wang, Y., He, G., Liu, P., and Chen, G., Chem. Sci., 2017, vol. 8, p. 7180.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  53. Viswanadh, N., Ghotekar, G.S., Thoke, M.B., Velayudham, R., Shaikh, A.C., Karthikeyan, M., and Muthukrishnan, M., Chem. Commun., 2018, vol. 54, p. 2252.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. College of Pharmaceutical Science and Institute of Drug Development & Chemical Biology, Zhejiang University of Technology, Hangzhou, China

    Quan Zheng & Guo-Wu Rao

  2. School of Pharmaceutical Sciences, Gannan Medical University, Ganzhou, China

    Jie Chen

Authors
  1. Quan Zheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jie Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Guo-Wu Rao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Guo-Wu Rao.

Additional information

Funding

This research was supported by Zhejiang Provincial Natural Science Foundation of China (grant no. LY19B020008).

Conflict of Interests

The authors declare the absence of conflict of interests.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zheng, Q., Chen, J. & Rao, GW. Recent Advances in C-O Bond Construction via C-H Activation. Russ J Org Chem 55, 569–586 (2019). https://doi.org/10.1134/S1070428019040249

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428019040249

Keywords

Search

Navigation