Skip to main content
SpringerLink
Log in

Theoretical Investigation on the Rhodium-Catalyzed Annulation of 2-Phenyl-1H-indole with Ethyl 2-Diazo-3-oxo-3-phenylpropanoate

  • CHEMICAL KINETICS AND CATALYSIS
  • Published:
Russian Journal of Physical Chemistry A Aims and scope Submit manuscript

Abstract

The reaction mechanisms of Rh-catalyzed annulation of 2-phenyl-1H-indole with ethyl 2-diazo-3-oxo-3-phenylpropanoate were investigated by employing the density functional theory (DFT) calculations. Five main steps are included in this reaction: N–H bond activation, C–H bond activation, N2 elimination, migratory insertion of carbine, and protonation. The rate-determining step is calculated to be the combined process of C–H bond activation and N2 elimination.

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

Scheme 1.
Scheme 2.
Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.

Similar content being viewed by others

REFERENCES

  1. T. V. Sravanthi and S. L. Manju, Eur. J. Pharm. Sci. 91, 1 (2016);

    Article  CAS  Google Scholar 

  2. P. Konopelski and M. Ufnal, Curr. Drug Metabol. 19, 883 (2018);

    Article  CAS  Google Scholar 

  3. C. A. Thomson, S. Dickinson, and G. T. Bowden, in Bioactive Compounds and Cancer (Humana Press, Totowa, NJ, 2010), p. 535.

    Google Scholar 

  4. R. Vanel, F. A. Miannay, E. Vauthey, and J. Lacour, Chem. Commun. 50, 12169 (2014);

    Article  CAS  Google Scholar 

  5. D. J. Gale, J. Lin, and J. F. K. Wilshire, Austral. J. Chem. 29, 2747 (1976);

    Article  CAS  Google Scholar 

  6. J. J. Lee, W. J. Lee, and J. P. Kim, Fibers Polym. 4, 66 (2003);

    Article  CAS  Google Scholar 

  7. J. R. Majer, Tetrahedron 9, 111 (1960).

    Article  CAS  Google Scholar 

  8. A. Berstad, J. Raa, and J. Valeur, Microb. Ecol. Health Disease 26, 27997 (2015).

    Google Scholar 

  9. T. Zhou, W. Guo, and Y. Xia, Chem.-Eur. J. 21, 9209 (2015).

    Article  CAS  Google Scholar 

  10. J. Roy, A. K. Jana, and D. Mal, Tetrahedron 68, 6099 (2012);

    Article  CAS  Google Scholar 

  11. F. F. Zhang, L. L. Gan, and C. H. Zhou, Bioorg. Med. Chem. Lett. 20, 1881 (2010);

    Article  CAS  Google Scholar 

  12. T. A. Choi, R. Czerwonka, W. Fröhner, M. P. Krahl, K. R. Reddy, S. G. Franzblau, and H. J. Knölker, ChemMedChem 1, 812 (2006);

    Article  CAS  Google Scholar 

  13. R. M. Adhikari, R. Mondal, B. K. Shah, and D. C. Neckers, J. Org. Chem. 72, 4727 (2007);

    Article  CAS  Google Scholar 

  14. C. J. Moody, Synlett 1994, 681 (1994).

    Article  Google Scholar 

  15. Z. Chen, B. Wang, J. Zhang, W. Yu, Z. Liu, and Y. Zhang, Org. Chem. Front. 2, 1107 (2015).

    Article  CAS  Google Scholar 

  16. B. Li, B. Zhang, X. Zhang, and X. Fan, Chem. Commun. 53, 1297 (2017).

    Article  CAS  Google Scholar 

  17. P. J. Stephens, F. J. Devlin, C. F. Chabalowski, and M. J. Frisch, J. Phys. Chem. 98, 11623 (1994);

    Article  CAS  Google Scholar 

  18. D. V. Chachkov and O. V. Mikhailov, Russ. J. Org. Chem. 54, 1952 (2009);

    Google Scholar 

  19. P. Winget and T. Clark, J. Comput. Chem. 25, 725 (2004).

    Article  CAS  Google Scholar 

  20. M. E. Belghiti, S. Echihi, A. Mahsoune, Y. Karzazi, A. Dafali, and I. Bahadur, J. Mol. Liq. 261, 62 (2018);

    Article  CAS  Google Scholar 

  21. W. R. Wadt and P. J. Hay, J. Chem. Phys. 82, 284 (1985);

    Article  CAS  Google Scholar 

  22. Q. Wei, Y. Dai, C. Chen, L. Shi, Z. Si, Y. Wan, Q. Zuo, D. Han, and Q. Duan, J. Mol. Struct. 1171, 786 (2018).

    Article  CAS  Google Scholar 

  23. K. Yoshizawa, Y. Shiota, and T. Yamabe, J. Chem. Phys. 111, 538 (1999);

    Article  CAS  Google Scholar 

  24. K. Fukui, J. Phys. Chem. 74, 4161 (1970);

    Article  CAS  Google Scholar 

  25. Y. Ni, Y. Pan, J. Zhang, X. Gu, X. Pan, J. Jiang, and Q. Wang, Comput. Theor. Chem. 1135, 11 (2018).

    Article  CAS  Google Scholar 

  26. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, et al., Gaussian 09, Revision D.01 (Gaussian Inc., Wallingford CT, 2009).

    Google Scholar 

  27. R. V. Belzen, C. J. Elsevier, A. Dedieu, and N. Veldman, Organomet. 22, 722 (2003);

    Article  Google Scholar 

  28. Y. Zhao and D. G. Truhlar, J. Chem. Theory Comput. 5, 324 (2009).

    Article  CAS  Google Scholar 

  29. J. J. Guerard and J. S. Arey, J. Chem. Theor. Comput. 9, 5046 (2013).

    Article  CAS  Google Scholar 

  30. Y. Liu, C. Sun, and S. Zhang, Theor. Chem. Acc. 132, 1 (2013);

    Article  CAS  Google Scholar 

  31. G. Igel-Mann, H. Stoll, and H. Preuss, Mol. Phys. 65, 1321 (1988);

    Article  CAS  Google Scholar 

  32. D. Andrae, U. Haeussermann, M. Dolg, H. Stoll, and H. Preuss, Theor. Chim. Acta 77, 123 (1990).

    Article  CAS  Google Scholar 

  33. K. Lv, Y. Y. Jiang, L. L. Han, T. Liu, and S. W. Bi, Mol. Catal. 462, 77 (2019);

    Article  CAS  Google Scholar 

  34. J. Zhang, C. H. Shan, T. Zhang, J. S. Song, T. Liu, and Y. Lan, Coord. Chem. Rev. 382, 69 (2019);

    Article  CAS  Google Scholar 

  35. L. L. Han, X. Y. Ma, Y. X. Liu, Z. Y. Yu, and T. Liu, Org. Chem. Front. 5, 725 (2018);

    Article  CAS  Google Scholar 

  36. J. Zhang, C. H. Shan, K. Lv, L. Zhu, Y. Y. Li, T. Liu, and Y. Lan, ChemCatChem 11, 1228 (2019);

    Article  CAS  Google Scholar 

  37. L. L. Han, Y. P. Li, and T. Liu, Dalton Trans. 47, 150 (2018).

    Article  CAS  Google Scholar 

  38. B. Li, S. Bi, Y. Liu, B. Ling, and P. Li, Organometallics 33, 3453 (2013).

    Article  Google Scholar 

  39. W. J. Chen and Z. Lin, Organometallics 34, 309 (2015).

    Article  Google Scholar 

Download references

Funding

This work was supported by the Natural Science Foundation of Shandong Province (no. ZR2019MB069).

Author information

Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Qufu Normal University, 273165, Qufu, Shandong, China

    Jiaying Sun, Zhangyu Yu & Tao Liu

  2. Department of Chemistry and Chemical Engineering, Jining University, 273155, Qufu, Shandong, China

    Zhangyu Yu & Tao Liu

Authors
  1. Jiaying Sun
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zhangyu Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tao Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Zhangyu Yu or Tao Liu.

Supplementary Information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sun, J., Yu, Z. & Liu, T. Theoretical Investigation on the Rhodium-Catalyzed Annulation of 2-Phenyl-1H-indole with Ethyl 2-Diazo-3-oxo-3-phenylpropanoate. Russ. J. Phys. Chem. 95, 2573–2577 (2021). https://doi.org/10.1134/S0036024421130239

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0036024421130239

Keywords:

Search

Navigation