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Baylis–Hillman Reaction Assisted by aliquat-336 and triphenylphosphine Under Ultrasound Radiation

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Abstract

The activation of Baylis–Hillman reaction by aliquat-336 and triphenylphosphine under ultrasound radiation is described. A significant improvement of the yield of Baylis–Hillman reaction was observed. We illustrate the effects of the solvent, the nature of the nucleophilic agent, the phase transfer catalyst and ultrasound, on the Baylis–Hillman reaction efficiency. The reaction examined involves methyl acrylate, which, in the presence of nucleophilic agent, forms a zwitterionic intermediate, which reacts with the aldehyde to subsequently give the product of the reaction. For all the aldehydes tested, it was found that ultrasound radiation in the presence of aliquat-336 could reduce the duration of the Baylis–Hillman reaction and improve the reaction efficiency. This method could be a clean, economical, efficient and safe technology in organic synthesis to prepare Baylis–Hillman adducts.

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References

  1. Xie P, Huang Y (2015) Org Biomol Chem 13:8578–8595

    Article  CAS  PubMed  Google Scholar 

  2. Barbier V, Couty F, David ORP (2015) Eur J Org Chem 2015:3679–3688

    Article  CAS  Google Scholar 

  3. Zeng XH, Wang HM, Ding MW (2015) Org Lett 17:2234–2237

    Article  CAS  PubMed  Google Scholar 

  4. Chen J, Li J, Wang J, Li H, Wang W, Guo Y (2015) Org Lett 17:2214–2217

    Article  CAS  PubMed  Google Scholar 

  5. Basavaiah D, Reddy BS, Badsara SS (2010) Chem Rev 110:5447–5674

    Article  CAS  PubMed  Google Scholar 

  6. Aggarwal VK, Dean DK, Mereu A, Williams R (2002) J Org Chem 67:510–514

    Article  CAS  PubMed  Google Scholar 

  7. Basavaiah D, Rao AJ, Satyanarayana T (2003) Chem Rev 103:811–891

    Article  CAS  PubMed  Google Scholar 

  8. Basavaiah D, Rao KV, Reddy RJ (2007) Chem Soc Rev 36:1581–1588

    Article  CAS  PubMed  Google Scholar 

  9. Basavaiah D, Rao PD, Hyma RS (1996) Tetrahedron 52:8001–8062

    Article  CAS  Google Scholar 

  10. Loh TP, Cao GQ, Pei J (1998) Tetrahedron Lett 39:1457–1460

    Article  CAS  Google Scholar 

  11. Wang B, Yu XM, Lin GQ (2001) Synlett 2001:904–906

    Article  Google Scholar 

  12. Anand RV, Baktharaman S, Singh VK (2002) Tetrahedron Lett 43:5393–5395

    Article  CAS  Google Scholar 

  13. Li CJ (2005) Chem Rev 105:3095–3165

    Article  CAS  PubMed  Google Scholar 

  14. Moussaoui Y, Ben Salem R (2003) J Tun Chem Soc 5:255–263

    Google Scholar 

  15. Moussaoui Y, Ben Salem R (2007) C R Chimie 10:630–636

    Article  CAS  Google Scholar 

  16. Cravotto G, Borretto E, Oliverio M, Procopio A, Penoni A (2015) Catal Commun 63:2–9

    Article  CAS  Google Scholar 

  17. Saïd K, Moussaoui Y, Kammoun M, Ben Salem R (2011) Ultrason Sonochem 18:23–27

    Article  CAS  PubMed  Google Scholar 

  18. Mhamdi L, Said K, Rigane G, Ben Salem R, Moussaoui Y (2016) J Tun Chem Soc 18:61–67

    Google Scholar 

  19. Mhamdi L, Saïd K, Moussaoui Y, Ben Salem R (2013) J Soc Chem Tunisie 15:149–162

    Google Scholar 

  20. Said K, Ben Salem R (2016) Adv Chem Eng Sci 6:111–123

    Article  CAS  Google Scholar 

  21. Cravotto G, Beggiato M, Penoni A, Palmisano G, Tollari S, Leveque JM, Bonrath W (2005) Tetrahedron Lett 46:2267–2271

    Article  CAS  Google Scholar 

  22. Cella R, Stefani HA (2006) Tetrahedron 62:5656–5662

    Article  CAS  Google Scholar 

  23. Pattarawarapan M, Jaita S, Wangngae S, Phakhodee W (2016) Tetrahedron Lett 57:1354–1358

    Article  CAS  Google Scholar 

  24. Song YL, Dong YF, Wu F, Yang T, Yang GL (2015) Ultrason Sonochem 22:119–124

    Article  CAS  PubMed  Google Scholar 

  25. Banerjee B (2017) Ultrason Sonochem 35:1–14

    Article  CAS  PubMed  Google Scholar 

  26. Banerjee B (2017) Ultrason Sonochem 35:15–35

    Article  CAS  PubMed  Google Scholar 

  27. Ge SQ, Hua YY, Xia M (2009) Ultrason Sonochem 16:232–236

    Article  CAS  PubMed  Google Scholar 

  28. Lorimer JP, Mason TJ (1987) Chem Soc Rev 16:239–274

    Article  CAS  Google Scholar 

  29. Datta B, Pasha MA (2012) Ultrason Sonochem 19:725–728

    Article  CAS  PubMed  Google Scholar 

  30. Chen BH, Li JT, Chen GF (2015) Ultrason Sonochem 23:59–65

    Article  CAS  PubMed  Google Scholar 

  31. Dupuy C, Petrier C, Sarandeses LA, Luche JL (1991) Synth Commun 21:643–651

    Article  CAS  Google Scholar 

  32. Dange PN, Kulkarni AV, Rathod VK (2015) Ultrason Sonochem 26:257–264

    Article  CAS  PubMed  Google Scholar 

  33. Harikumar K, Rajendran V (2015) Inter J Chem Sci Appl 6:12–28

    CAS  Google Scholar 

  34. Sancheti SV, Gogate PR (2017) Ultrason Sonochem 36:527–543

    Article  CAS  PubMed  Google Scholar 

  35. Alonso F, Beletskaya IP, Yus M (2005) Tetrahedron 61:11771–11835

    Article  CAS  Google Scholar 

  36. Margulis MA (2004) High Energ Chem 38:135–142

    Article  CAS  Google Scholar 

  37. Singh BS, Lobo HR, Pinjari DV, Jarag KJ, Pandit AB, Shankarling GS (2013) Ultrason Sonochem 20:633–639

    Article  CAS  PubMed  Google Scholar 

  38. Coelho F, Almeida WP, Veronese D, Mateus CR, Lopes ECS, Rossi RC, Silveira GPC, Pavam CH (2002) Tetrahedron 58:7437–7447

    Article  CAS  Google Scholar 

  39. Ge SQ, Hua YY, Xia M (2009) Ultrason Sonochem 16:743–746

    Article  CAS  PubMed  Google Scholar 

  40. Mamaghani M, Dastmard S (2009) Ultrason Sonochem 16:445–447

    Article  CAS  PubMed  Google Scholar 

  41. Yamada YMA, Ikegami S (2000) Tetrahedron Lett 41:2165–2169

    Article  CAS  Google Scholar 

  42. Shi M, Xu YM (2002) Eur J Org Chem 2002:696–701

    Article  Google Scholar 

  43. Shi M, Xu YM, Zhao GL, Wu XF (2002) Eur J Org Chem 2002:3666–3679

    Article  Google Scholar 

  44. Shi M, Zhao GL (2002) Tetrahedron Lett 43:4499–4502

    Article  CAS  Google Scholar 

  45. Bode ML, Kaye PT (1991) Tetrahedron Lett 32:5611–6514

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors would like to express their profound gratitude to the Tunisian Ministry of Higher Education for its financial support.

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Authors and Affiliations

  1. Organic Chemistry Laboratory (LR17ES08), Faculty of Sciences of Sfax, University of Sfax, Sfax, Tunisia

    Layla Mhamdi, Khemais Said, Dhiab Atoui, Younes Moussaoui & Ridha Ben Salem

  2. Faculty of Sciences of Gafsa, University of Gafsa, 2112, Gafsa, Tunisia

    Younes Moussaoui

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  1. Layla Mhamdi
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  2. Khemais Said
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  3. Dhiab Atoui
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  4. Younes Moussaoui
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  5. Ridha Ben Salem
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Correspondence to Younes Moussaoui.

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Mhamdi, L., Said, K., Atoui, D. et al. Baylis–Hillman Reaction Assisted by aliquat-336 and triphenylphosphine Under Ultrasound Radiation. Chemistry Africa 1, 11–16 (2018). https://doi.org/10.1007/s42250-018-0006-8

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  • DOI: https://doi.org/10.1007/s42250-018-0006-8

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