Advertisement

Catalysis Letters

, Volume 149, Issue 7, pp 1934–1940 | Cite as

Electrostatically Enhanced Sulfuric Acid: A Strong Brønsted Acidic Catalyst for Multi-Component Reactions

  • Mohadese Yaghoobi Anzabi
  • Hossein Yazdani
  • Ayoob BazgirEmail author
Article
  • 17 Downloads

Abstract

A new electrostatically enhanced sulfuric acid as a strong Brønsted acidic catalyst has been developed for multi-component reactions. A positively charged center in the catalyst electrostatically activates it for acid-catalyzed multi-component reactions and afforded desired products in short reaction time and near room temperature in EtOH as a green solvent.

Graphical Abstract

Keywords

Electrostatically enhanced sulfuric acid Brønsted acid catalyst Multi-component reaction GBB reaction Biginelli reaction 

Notes

Acknowledgements

We gratefully acknowledge the financial support from the Research Council of Shahid Beheshti University and the Iran National Science Foundation (INSF).

Supplementary material

10562_2019_2776_MOESM1_ESM.docx (4.8 mb)
Supplementary material 1 (DOCX 4878 kb)

References

  1. 1.
    D’Souza DM, Müller TJJ (2007) Chem Soc Rev 36:1095–1108CrossRefGoogle Scholar
  2. 2.
    Jiang B, Rajale T, Wever W, Tu SJ, Li G (2010) Chem Asian J 5:2318–2335CrossRefGoogle Scholar
  3. 3.
    Bienaymé H, Hulme C, Oddon G, Schmitt P (2000) Chem Eur J 6:3321–3329CrossRefGoogle Scholar
  4. 4.
    Cioc RC, Rujiter E, Orru RVA (2014) Green Chem 16:2958–2975CrossRefGoogle Scholar
  5. 5.
    Parmar D, Sugiono E, Raja S, Rueping M (2014) Chem Rev 114:9047–9153CrossRefGoogle Scholar
  6. 6.
    Xie YB, Ye SP, Chen WF, Hu YL, Li DJ, Wang L (2017) Asian J Org Chem 6:746–750CrossRefGoogle Scholar
  7. 7.
    Karunaratne CV, Sarkisian RG, Reeves J, Deng Y, Wheeler KA, Wang H (2017) Org Biomol Chem 15:4933–4936CrossRefGoogle Scholar
  8. 8.
    Cioc RC, Preschel H, Dvan der Heijden G, Ruijter E, Orru RVA (2016) Chem Eur J 22:7837–7842CrossRefGoogle Scholar
  9. 9.
    Boomhoff M, Ukis R, Schneider C (2015) J Org Chem 80:8236–8244CrossRefGoogle Scholar
  10. 10.
    Raja VPA, Tenti G, Perumal S, Menendez JC (2014) Chem Commun 50:12270–12272CrossRefGoogle Scholar
  11. 11.
    Sharma P, Gupta M (2015) Green Chem 17:1100–1106CrossRefGoogle Scholar
  12. 12.
    Cai Q, Li DK, Zhou RR, Zhuang SY, Ma JT, Wu YD, Wu AX (2016) J Org Chem 81:8104–8111CrossRefGoogle Scholar
  13. 13.
    Kaupmees K, Tolstoluzhsky N, Raja S, Rueping M, Leito I (2013) Angew Chem Int Ed 52:1569–1572CrossRefGoogle Scholar
  14. 14.
    Samet M, Buhle J, Zhou Y, Kass SR (2015) J Am Chem Soc 137:4678–4680CrossRefGoogle Scholar
  15. 15.
    Ma J, Kass SR (2016) Org Lett 18:5812–5815CrossRefGoogle Scholar
  16. 16.
    Fan Y, Kass SR (2016) Org Lett 18:188–191CrossRefGoogle Scholar
  17. 17.
    Kozhevnikov IV (1998) Chem Rev 98:171–198CrossRefGoogle Scholar
  18. 18.
    Rueping M, Kuenkel A, Atodiresei I (2011) Chem Soc Rev 40:4539–4549CrossRefGoogle Scholar
  19. 19.
    Wu J, Du X, Ma J, Zhang Y, Shi Q, Luo L, Song B, Yang S, Hu D (2014) Green Chem 16:3210–3217CrossRefGoogle Scholar
  20. 20.
    Li M, Zhang B, Gu Y (2012) Green Chem 14:2421–2428CrossRefGoogle Scholar
  21. 21.
    Takemoto Y (2005) Org Biomol Chem 3:4299–4306CrossRefGoogle Scholar
  22. 22.
    Wieting JM, Fisher TJ, Schafer AG, Visco MD, Gallucci JC, Mattson A (2015) Eur J Org Chem 2015:525–533CrossRefGoogle Scholar
  23. 23.
    Vafaeezadeh M, Alinezhad H (2016) J Mol Liq 218:95–105CrossRefGoogle Scholar
  24. 24.
    Sandhu S, Sandhu JS (2012) ARKIVOC (i):66-133Google Scholar
  25. 25.
    Salehi P, Dabiri M, Zolfigol MA, Bodaghi Fard MA (2003) Tetrahedron Lett 44:2889–2891CrossRefGoogle Scholar
  26. 26.
    Kolvari E, Koukabi N, Hosseini MM, Vahidian M, Ghobadi E (2016) RSC Adv 6:7419–7425CrossRefGoogle Scholar
  27. 27.
    Tu S, Fang F, Zhu S, Li T, Zhang X, Zhuang Q (2004) J Heterocycl Chem 41:253–257CrossRefGoogle Scholar
  28. 28.
    Rezaei R, Malek S, Sheikhi MR, Mohammadi MK (2013) Chem J Mold 8:101–106CrossRefGoogle Scholar
  29. 29.
    Chen WY, Qin SD, Jin JR (2007) Synth Commun 37:47–52CrossRefGoogle Scholar
  30. 30.
    Akritopoulou-Zanze I, Wakefield BD, Gasiecki A, Kalvin D, Johnson EF, Kovar P, Djuric SW (2011) Bioorg Med Chem Lett 21:1480–1483CrossRefGoogle Scholar
  31. 31.
    Guchhait SK, Chaudhary V, Madaan C (2012) Org Biomol Chem 10:9271–9277CrossRefGoogle Scholar
  32. 32.
    Hajjami M, Bakhti F, Ghiasbeygi E (2015) Croat Chem Acta 88:197–205CrossRefGoogle Scholar
  33. 33.
    Shiri L, Zarei S, Kazemi M, Sheikh D (2018) Appl Organom Chem 32:3938CrossRefGoogle Scholar
  34. 34.
    Reddy BVS, Venkateswarlu A, Madan Ch, Vinu A (2011) Tetrahedron Lett 52:1891–1894CrossRefGoogle Scholar
  35. 35.
    Ghorbani-Choghamarani A, Tahmasbi B (2016) New J Chem 40:1205–1212CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Mohadese Yaghoobi Anzabi
    • 1
  • Hossein Yazdani
    • 1
  • Ayoob Bazgir
    • 1
    Email author
  1. 1.Department of ChemistryShahid Beheshti University G.CTehranIran

Personalised recommendations