Skip to main content
SpringerLink
Log in

FeCl3·6H2O-catalyzed synthesis of β-ketothioesters from chain α-oxo ketene dithioactals

  • Published:
Chemical Research in Chinese Universities Aims and scope

Abstract

A FeCl3·6H2O-catalyzed synthesis of β-ketothioesters from the hydrolysis reaction of chain α-oxoketene dithioacetals was carried out. Subsequently, we explored the FeCl3·6H2O-catalyzed Friedel-Crafts alkylation of the synthesized β-ketothioesters with alcohols in CH3CN at 25 °C, affording the desired α-alkylated β-ketothioesters in excellent yields. Wide scope of the substrates, use of inexpensive reagents, high yields under mild reaction conditions are notable features of these reactions.

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. Ley S. V., Woodward P. R., Tetrahedron Lett., 1987, 28, 3019

    Article  CAS  Google Scholar 

  2. Fortner K. C., Shair M. D., J. Am. Chem. Soc., 2007, 129, 1032

    Article  CAS  Google Scholar 

  3. Bahlinger A., Fritz S. P., Wennemers H., Angew. Chem. Int. Ed., 2014, 53, 8779

    Article  CAS  Google Scholar 

  4. Das A., Khosla C., Acc. Chem. Res., 2009, 42, 631

    Article  CAS  Google Scholar 

  5. Chen A. Y., Schnarr N. A., Kim C. Y., Cane D. E., Khosla C., J. Am. Chem. Soc., 2006, 128, 3067

    Article  CAS  Google Scholar 

  6. Aron Z. D., Dorrestein P. C., Blackhall J. R., Kelleher N. L., Walsh C. T., J. Am. Chem. Soc., 2005, 127, 14986

    Article  CAS  Google Scholar 

  7. Duus F., Jakorsen P., Lawwwn S., Tetrahedron, 1968, 24, 5323

    Article  CAS  Google Scholar 

  8. Xin D., Burgess K. A., Org. Lett., 2014, 16, 2108

    Article  CAS  Google Scholar 

  9. Davis J. B., Bailey J. D., Sello J. K., Org. Lett., 2009, 11, 2984

    Article  CAS  Google Scholar 

  10. Hayashi Y., Miyamoto Y., Shoji M., Tetrahdron Lett., 2002, 43, 4079

    Article  CAS  Google Scholar 

  11. Yu H. F., Yu Z. K., Angew. Chem., Int. Ed., 2009, 48, 2929

    Article  CAS  Google Scholar 

  12. Yu H. F., Jin W. W., Sun C. L., Yu Z. K., Angew. Chem. Int. Ed., 2010, 49, 5792

    Article  CAS  Google Scholar 

  13. Liu Y., Barry B. D., Yu H. F., Liu J. Q., Liao P. Q., Bi X. H., Org. Lett., 2013, 15, 2608

    Article  CAS  Google Scholar 

  14. Fang Z. X., Liu Y., Barry B. D., Liao P. Q., Bi X. H., Org. Lett., 2015, 17, 782

    Article  CAS  Google Scholar 

  15. Yu H. F., Zhang Y. M., Li T. C., Liao P. Q., Diao Q. P., Xin G., Meng Q. L., Hou D. Y., RSC Adv., 2015, 5, 11293

    Article  CAS  Google Scholar 

  16. Ming W. B., Liu X. C., Wang L. J., Liu J., Wang M., Org. Lett., 2015, 17, 1746

    Article  CAS  Google Scholar 

  17. Luo H. M., Pan L., Xu X. X., Liu Q., J. Org. Chem., 2015, 80, 8282

    Article  CAS  Google Scholar 

  18. Jin W. W., Du W. M., Yang Q., Yu H. F., Yu Z. K., Org. Lett., 2011, 13, 4272

    Article  CAS  Google Scholar 

  19. Dong Y., Wang M., Liu J., Chem. Commun., 2011, 47, 7380

    Article  CAS  Google Scholar 

  20. Yu H. F., Liao P. Q., Tetrahedron Lett., 2016, 57, 2868

    Article  CAS  Google Scholar 

  21. Yu H. F., Wang D. L., Zhao H., Hou D. Y., Chin. J. Org. Chem., 2011, 31, 1949

    CAS  Google Scholar 

  22. Yu H. F., Chin. J. Chem., 2012, 23, 367

    Article  Google Scholar 

  23. Yu H. F., Liao P. Q., Chem. J. Chinese Universities, 2012, 33(9), 1969

    CAS  Google Scholar 

  24. Yu H. F., Synthetic Commun., 2013, 43, 1280

    Article  CAS  Google Scholar 

  25. Song Y., Tang X. S., Hou X. M., Bai Y., Chin. J. Org. Chem., 2013, 33, 76

    Article  CAS  Google Scholar 

  26. Yang Q., Wang L. D., Guo T. L., Yu Z. K., J. Org. Chem., 2012, 77, 8355

    Article  CAS  Google Scholar 

  27. Wang Y. M., Bi X. H., Li D. H., Liao P. Q., Wang Y. D., Yang J., Zhang Q., Liu Q., Chem. Commun., 2011, 47, 809

    Article  CAS  Google Scholar 

  28. Huang D. S., Wang H. N., Xue F. Z., Shi Y. A., J. Org. Chem., 2011, 76, 7269

    Article  CAS  Google Scholar 

  29. Yu H. F., Li T. C., Liao P. Q., Synthesis, 2012, 44, 3743

    Article  CAS  Google Scholar 

  30. Zhao H., Zhang F. W., Yu H. F., Liao P. Q., Diao Q. P., Li T. C., Xin G., Hou D. Y., Chin. J. Org. Chem., 2015, 35, 1493

    Article  CAS  Google Scholar 

  31. Yu H. F., Liao P. Q., Chem. Res. Chinese Universities, 2016, 32(3), 390

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Chemistry and Life Science, Anshan Normal University, Anshan, 114007, P. R. China

    Hui Zhao, Quanping Diao, Haifeng Yu, Tiechun Li & Dongyan Hou

  2. Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun, 130024, P. R. China

    Haifeng Yu & Peiqiu Liao

Authors
  1. Hui Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Quanping Diao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Haifeng Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tiechun Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Peiqiu Liao
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Dongyan Hou
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Haifeng Yu or Dongyan Hou.

Additional information

Supported by the Fundamental Research Funds for the Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, China(No.130028652), the Natural Science Foundation of Liaoning Province, China(No.201602002), the Foundation of Liaoning Province Education Administration, China(No.L2015003) and the National Natural Science Foundation of China(No.20902010).

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhao, H., Diao, Q., Yu, H. et al. FeCl3·6H2O-catalyzed synthesis of β-ketothioesters from chain α-oxo ketene dithioactals. Chem. Res. Chin. Univ. 33, 746–752 (2017). https://doi.org/10.1007/s40242-017-7082-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40242-017-7082-1

Keywords

Search

Navigation