Skip to main content
SpringerLink
Log in

Iron chloride hexahydrate-catalyzed Friedel-Crafts akylation of cyclic ketene dithioacetals with alcohols

  • Published:
Chemical Research in Chinese Universities Aims and scope

Abstract

A cost-effective and environmentally compliance FeCl3·6H2O catalyzed Friedel-Crafts alkylation of cyclic ketene dithioacetals with alcohols was developed. The reaction was efficient in the presence of catalyst loading as low as 5%(molar fraction) in CH2Cl2 solvent at room temperature or under reflux conditions. A wide range of alkylated ketene dithioacetals were synthesized in excellent yields.

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. You S. L., Cai Q., Zeng M., Chem. Soc. Rev., 2009, 38, 2190

    Article  CAS  Google Scholar 

  2. Gao J. R., Wu H., Xiang B., Yu W. B., Han L., Jia Y. X., J. Am. Chem. Soc., 2013, 135, 2983

    Article  CAS  Google Scholar 

  3. Zhai C. W., Xing D., Jing C. C., Zhou J., Wang C. J., Wang D. W., Hu W. H., Org. Lett., 2014, 16, 2934

    Article  CAS  Google Scholar 

  4. Li C., Guo F. F., Xu K., Zhang S., Hu Y. B., Zha Z. G., Wang Z. Y., Org. Lett., 2014, 16, 3192

    Article  CAS  Google Scholar 

  5. Matuszek K., Chrobok A., Hogg J. M., Coleman F., Swadźba-Kwaśny M., Green Chem., 2015, 17, 4255

    Article  CAS  Google Scholar 

  6. Guillena G., Ramón D. J., Yus M., Angew. Chem. Int. Ed. 2007, 46, 2358

    Article  CAS  Google Scholar 

  7. Tsoung J., Krämer K., Zajdlik A., Liébert C., Lautens M., J. Org. Chem., 2011, 76, 9031

    Article  CAS  Google Scholar 

  8. Liébert C., Brinks M. K., Capacci A. G., Fleming M. J., Lautens M., Org. Lett., 2011, 13, 3000

    Article  Google Scholar 

  9. Nokami T., Yamane Y., Oshitani S., Kobayashi J., Matsui S., Nishihara T, Uno H., Hayase S., Itoh T., Org. Lett., 2015, 17, 3182

    Article  CAS  Google Scholar 

  10. Pan L., Liu, Q., Synlett., 2011, 8, 1073

    Google Scholar 

  11. Pan L., Bi X. H., Liu Q., Chem. Soc. Rev., 2013, 42, 1251

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  14. 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 

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

    Article  CAS  Google Scholar 

  16. Bi X. H., Dong D. W., Liu Q., J. Am. Chem. Soc., 2005, 127, 4578

    Article  CAS  Google Scholar 

  17. Zhang L., Liang F. S., Cheng X., Liu Q., J. Org. Chem., 2009, 74, 899

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    Article  Google Scholar 

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

    CAS  Google Scholar 

  25. Yu H. F., Synth. Commun., 2013, 43, 1280

    Article  CAS  Google Scholar 

  26. Yu H. F., Liao P. Q., Chemistry, 2013, 5, 435

    Google Scholar 

  27. Zhang Q., Sun S. G., Hu J. L., Liu Q., Tan J., J. Org. Chem., 2007, 72, 139

    Article  CAS  Google Scholar 

  28. Liang D., Wang M., Bekturhun B., Xiong B., Liu Q., Adv. Synth. Catal., 2010, 352, 1593

    Article  CAS  Google Scholar 

  29. Song J. N., Fang Z. X., Liu Y., Li R., Xu L. X., Barry B. D., Liu Q., Bi X. H., Liao P. Q., Synlett., 2011, 2551

    Google Scholar 

  30. Sperança A., Godoi B., Zeni G., J. Org. Chem., 2013, 78, 1630

    Article  Google Scholar 

  31. Yang Q., Wu P., Chen J. P., Yu Z. K., Chem. Commun., 2014, 50, 6337

    Article  CAS  Google Scholar 

  32. Mantovani A. C., Goulart T. A. C., Back D. F., Henrique-Menezes P., Zeni G., J. Org. Chem., 2014 79, 10526

    Article  CAS  Google Scholar 

  33. Bilheri F. N., Stein A. L., Zeni G., Adv. Synth. Catal., 2015, 357, 1221

    Article  CAS  Google Scholar 

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

    Google Scholar 

  35. 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 

Download references

Author information

Authors and Affiliations

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

    Haifeng Yu

  2. Department of Chemistry, Northeast Normal University, Changchun, 130024, P. R. China

    Peiqiu Liao

Authors
  1. Haifeng Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Peiqiu Liao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Haifeng Yu.

Additional information

Supported by the National Natural Science Foundation of China(No.20902010), the Foundation of Liaoning Provincial Education Administration, China(No.L2015003) and the Science Foundation of Anshan City, China(Nos.2012KJ02, 2014KJ05).

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yu, H., Liao, P. Iron chloride hexahydrate-catalyzed Friedel-Crafts akylation of cyclic ketene dithioacetals with alcohols. Chem. Res. Chin. Univ. 32, 390–395 (2016). https://doi.org/10.1007/s40242-016-5482-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40242-016-5482-2

Keywords

Search

Navigation