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Sonochemical synthesis of lithium fluoride nano cubic as an active and simple catalyst for thia-Michael addition process: synthesis and structural characterization of β-aryl-β-mercapto ketones

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Abstract

LiF nano cubic, with an average particle size of 21.6 nm, was synthesized sonochemically, using tetrabutylammonium fluoride as the fluoride source and characterized by SEM-EDX and XRD. This was applied, as a heterogeneous nano-catalyst, to synthesize some β-aryl-β-mercapto ketone derivatives via thia-Michael addition reactions with excellent yields at room temperature. In this catalytic system, the products of undesirable side reactions resulting from 1,2-addition, polymerization, bis-addition and oxidative coupling of thiols were not observed. The products were characterized by elemental analysis, IR, NMR and mass, and also single crystal X-ray determination for 3-(4-chlorophenylthio)-1,3-diphenylpropan-1-one, 1-phenyl-3-(phenylthio)-3-p-tolylpropan-1-one, 3-(p-tolylthio)-1-phenyl-3-p-tolylpropan-1-one and 3-(4-chlorophenylthio)-1-phenyl-3-p-tolylpropan-1-one. Following the recent search on the CSD, it is found that there is no report on the structure determination of [R1]C[H][CH2C(O)R2][S-Ar] β-aryl-β-mercapto ketones with the S-C6H5, S-C6H4-p-CH3 and S-C6H4-p-Cl segments (as S-Ar).

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References

  1. Y. Hui, J. Jiang, W. Wang, W. Chen, Y. Cai, L. Lin, X. Liu, X. Feng, Angew. Chem. Int. Ed. 49, 4290 (2010)

    Article  CAS  Google Scholar 

  2. Y. Qian, G.-Y. Ma, Y. Yang, K. Cheng, Q.-Z. Zheng, W.-J. Mao, L. Shi, J. Zhao, H.-L. Zhu, Bioorg. Med. Chem. 18, 4310 (2010)

    Article  CAS  Google Scholar 

  3. C. González-Rodríguez, S.R. Parsons, A.L. Thompson, M.C. Willis, Chem. Eur. J. 16, 10950 (2010)

    Article  Google Scholar 

  4. A. Kumar, Akanksha, Tetrahedron Lett. 48, 8730 (2007)

    Article  CAS  Google Scholar 

  5. M.S. Abaee, S. Cheraghi, S. Navidipoor, M.M. Mojtahedi, S. Forghani, Tetrahedron Lett. 53, 4405 (2012)

    Article  CAS  Google Scholar 

  6. M. Bandini, P.G. Cozzi, M. Giacomini, P. Melchiorre, S. Selva, A. Umani-Ronchi, J. Org. Chem. 67, 3700 (2002)

    Article  CAS  Google Scholar 

  7. M.M. Alam, R. Varala, S.R. Adapa, Tetrahedron Lett. 44, 5115 (2003)

    Article  CAS  Google Scholar 

  8. K. Suzuki, A. Ikegawa, T. Mukaiyama, Bull. Soc. Chem. Jpn. 55, 3277 (1982)

    Article  CAS  Google Scholar 

  9. A. Sarkar, S.R. Roy, A.K. Chakraborti, Chem. Commun. 47, 4538 (2011)

    Article  CAS  Google Scholar 

  10. S. Banerjee, J. Das, R.P. Alvarez, S. Santra, New J. Chem. 34, 302 (2010)

    Article  CAS  Google Scholar 

  11. M. Verziu, M. Florea, S. Simon, V. Simon, P. Filip, V.I. Parvulescu, C. Hardacre, J. Catal. 263, 56 (2009)

    Article  CAS  Google Scholar 

  12. M. Cavazza, F. Pietra, Tetrahedron Lett. 45, 3633 (2004)

    Article  CAS  Google Scholar 

  13. S. Gao, C. Tseng, C.H. Tsai, C.-F. Yao, Tetrahedron 64, 1955 (2008)

    Article  CAS  Google Scholar 

  14. A. Heydari, S. Khaksar, J. Akbari, M. Esfandyari, M. Pourayoubi, M. Tajbakhsh, Tetrahedron Lett. 48, 1135 (2007)

    Article  CAS  Google Scholar 

  15. Z. Shobeiri, M. Pourayoubi, A. Heydari, T.M. Percino, M.A. Leyva Ramírez, C. R. Chim. 14, 597 (2011)

  16. F.H. Allen, Acta Cryst. Sect. B 58, 380 (2002)

    Article  Google Scholar 

  17. R. Sarraf-Mamoory, S. Nadery, N. Riahi-Noori, Chem. Eng. Comm. 194, 1022 (2007)

    Article  CAS  Google Scholar 

  18. S.K. Garg, R. Kumar, A.K. Chakraborti, Synlett 1370 (2005)

  19. S.K. Garg, R. Kumar, A.K. Chakraborti, Tetrahedron Lett. 46, 1721 (2005)

    Article  CAS  Google Scholar 

  20. G.L. Khatik, G. Sharma, R. Kumar, A.K. Chakraborti, Tetrahedron 63, 1200 (2007)

    Article  CAS  Google Scholar 

  21. Y. Abrouki, M. Zahouily, A. Rayadh, B. Bahlaouan, S. Sebti, Tetrahedron Lett. 43, 8951 (2002)

    Article  CAS  Google Scholar 

  22. J. Skarżewski, M. Zielińska-Błajet, I. Turowska-Tyrk, Tetrahedron Asymmetry 12, 1923 (2001)

    Article  Google Scholar 

  23. C.-M. Chu, S. Gao, M.N.V. Sastry, C.-F. Yao, Tetrahedron Lett. 46, 4971 (2005)

    Article  CAS  Google Scholar 

  24. M. Zahouily, Y. Abrouki, A. Rayadh, S. Sebti, H. Dhimane, M. David, Tetrahedron Lett. 44, 2463 (2003)

    Article  CAS  Google Scholar 

  25. J.S. Yadav, B.V.S. Reddy, G. Baishya, J. Org. Chem. 68, 7098 (2003)

    Article  CAS  Google Scholar 

  26. K. Tokuno, M. Matsui, F. Miyoshi, Y. Asao, T. Ohashi, K. Kihara, Acta Cryst. Sect. C 42, 85 (1986)

    Article  Google Scholar 

  27. M. Yaeghoobi, H. Khaledi, Z. Abdullah, N. Abd Rahman, Acta Cryst. Sect. E67, o1693 (2011)

    Google Scholar 

  28. G. Morgant, X. Labouze, B. Viossat, J.-C. Lancelot, N.H. Dung, Acta Cryst. Sect. C 52, 923 (1996)

    Article  Google Scholar 

  29. S. Koda, T. Kimura, T. Kondo, H. Mitome, Ultrason. Sonochem. 10, 149 (2003)

    Article  CAS  Google Scholar 

  30. Oxford Diffraction Ltd., Xcalibur CCD System, Crys Alis Software System, Version 1.171, (Oxford, England, 2006)

  31. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, J. Appl. Cryst. 26, 343 (1993)

    Article  Google Scholar 

  32. G.M. Sheldrick, Acta Cryst. Sect. A 64, 112 (2008)

    Article  CAS  Google Scholar 

  33. L.J. Farrugia, J. Appl. Cryst. 32, 837 (1999)

    Article  CAS  Google Scholar 

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Acknowledgments

The authors gratefully acknowledge the support of this work by the Ferdowsi University of Mashhad. We are grateful to CEITEC-Central European Institute of Technology for determining the structural analysis by single-crystal X-ray diffraction method (CZ.1.05/1.1.00/02.0068).

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Authors and Affiliations

  1. Department of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran

    Zohreh Shobeiri & Mehrdad Pourayoubi

  2. Department of Chemistry, Faculty of Science, Masaryk University, Kotlarska 2, 61137, Brno, Czech Republic

    Marek Nečas & Michal Babiak

  3. Department of Physics, Faculty of Sciences, University of Novi Sad, 21000, Novi Sad, Serbia

    Vladimir Divjakovic

  4. CEITEC - Central European Institute of Technology, Masaryk University, Kamenice 5, 62500, Brno, Czech Republic

    Marek Nečas & Michal Babiak

Authors
  1. Zohreh Shobeiri
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  2. Mehrdad Pourayoubi
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  3. Marek Nečas
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  4. Vladimir Divjakovic
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  5. Michal Babiak
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Correspondence to Mehrdad Pourayoubi.

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Shobeiri, Z., Pourayoubi, M., Nečas, M. et al. Sonochemical synthesis of lithium fluoride nano cubic as an active and simple catalyst for thia-Michael addition process: synthesis and structural characterization of β-aryl-β-mercapto ketones. J IRAN CHEM SOC 12, 245–255 (2015). https://doi.org/10.1007/s13738-014-0479-6

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  • DOI: https://doi.org/10.1007/s13738-014-0479-6

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