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Cage Like Al-KIT-5 Mesoporous Materials for C–C Bond Formation Reactions Under Solvent Free Conditions

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Abstract

The C–C bond forming reactions are of fundamental importance in chemistry. As a result there is ever growing interest for chemists to develop new methods for C–C bond formation. We report here three dimensional nano-cage mesoporous aluminosilicate materials Al-KIT-5 which exhibited very good catalytic activity for Mukaiyama-aldol and Mukaiyama–Michael reactions under solvent free condition. Mukaiyama-aldol and Mukaiyama–Michael reactions of silyl ketene acetal with aldehyde and α, β-unsaturated carbonyl compounds produced β-hydroxy esters and 1, 5-dicarbonyl compounds, respectively in good yields. The product selectivity was found to be 100 % in a short reaction period. The high acidity, 3D pores, and a huge space in the nano-cages materials make them attractive candidate for carrying out important organic reactions. The catalyst provide a simple, easy to handle method, and could be used to solve the problems of corrosion, toxicity, waste production, and high cost that are being currently encountered by the conventional homogeneous catalysts.

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References

  1. Kresge CT, Leonowicz ME, Roth WJ, Vartuli JC, Beck JS (1992) Nature 359:710

    Article  CAS  Google Scholar 

  2. Corma A (1997) Chem Rev 97:2373

    Article  CAS  Google Scholar 

  3. Zhao D, Feng J, Huo Q, Melosh N, Fredickson GH, Chmelka BF, Stucky GD (1998) Science 279:548

    Article  CAS  Google Scholar 

  4. Srinivasu P, Alam S, Balasubramanian VV, Velmathi S, Sawant DP, Bohlmann W, Mirajkar SP, Ariga K, Halligudi SB, Vinu A (2008) Adv Funct Mater 18:640

    Article  CAS  Google Scholar 

  5. Huo Q, Leon R, Petroff PM, Stucky GD (1995) Science 268:1324

    Article  CAS  Google Scholar 

  6. Huo Q, Margolese DI, Ciesla U, Demuth DG, Feng P, Gier T, Sieger P, Firouzi A, Chmelka BF, Schuth F (1994) Chem Mater 6:1176

    Article  CAS  Google Scholar 

  7. Kleitz F, Liu D, Anil Kumar GM, Park IS, Solovyov LA, Shmakov AN, Ryoo R (2003) J Phys Chem B 107:14296

    Article  CAS  Google Scholar 

  8. Balasubramanian VV, Srinivasu P, Anand C, Pal RR, Ariga K, Velmathi S, Vinu A (2008) Micropor Mesopor Mater 114:303

    Article  CAS  Google Scholar 

  9. Vinu A, Kalita P, Balasubramanian VV, Oveisi H, Selvan T, Mano A, Chari MA, Subba Reddy BV (2009) Tetrahedron Lett 50:7132

    Article  CAS  Google Scholar 

  10. Chakravarti R, Kalita P, Tamil Selvan S, Oveisi H, Balasubramanian VV, Lakshmi Kantam M, Vinu A (2010) Green Chem 12:49

    Article  CAS  Google Scholar 

  11. Chakravarti R, Oveisi H, Kalita P, Pal RR, Halligudi SB, Kantam ML, Vinu A (2009) Micropor Mesopor Mater 123:338

    Article  CAS  Google Scholar 

  12. Kalita P, Pegu CD, Dutta P, Baruah PK (2014) J Mol Catal A 394:145

    Article  CAS  Google Scholar 

  13. Kalita P, Sathyaseelan B, Mano A, Javaid Zaidi SM, Chari MA, Vinu A (2010) Chem Eur J 16:2843

    Article  CAS  Google Scholar 

  14. Narasaka K, Soai K, Mukaiyama T (1974) Chem Lett 3:1223

    Article  Google Scholar 

  15. Saigo K, Osaki M, Mukaiyama T (1976) Chem Lett 5:163

    Article  Google Scholar 

  16. Narasaka K, Soai K, Aikawa A, Mukaiyama T (1976) Bull Chem Soc Jpn 49:779

    Article  CAS  Google Scholar 

  17. Yamamoto H, Oshima K (2002) Main group metals in organic synthesis, vol 2. Wiley, Weinheim, p 409

    Google Scholar 

  18. Bunce RA, Schlecht MF, Dauben WG, Heathcock CH (1983) Tetrahedron Lett 24:4943

    Article  CAS  Google Scholar 

  19. Grieco PA, Cooke RJ, Henry KJ, Vander Roest JM (1991) Tetrahedron Lett 32:4665

    Article  CAS  Google Scholar 

  20. Liu D, Hong S, Corey EJ (2006) J Am Chem Soc 128:8160

    Article  CAS  Google Scholar 

  21. Arigan ZS, Suschitiky H (1961) J Chem Soc 2242

  22. Krohnke F (1976) Synthesis 1

  23. Constable EC, Thompson AMW Cargill (1992) J Chem Soc Dalton Trans 2947

  24. Butler IR, Mcdonald SJ, Hursthouse MB, Malik KMA (1995) Polyhedron 14:529

    Article  CAS  Google Scholar 

  25. Noyori R, Nishida I, Sakata J (1983) J Am Chem Soc 105:1598

    Article  CAS  Google Scholar 

  26. Ranu BC, Saha M, Bhar S (1993) Tetrahedron Lett 34:1989

    Article  CAS  Google Scholar 

  27. Reetz MT, Giebel D (2000) Angew Chem 39:2498

    Article  CAS  Google Scholar 

  28. Mitshuhashi H, Tanaka M, Nakamura H, Arata K (2001) Appl Catal A Gen 208:1

    Article  Google Scholar 

  29. Gu W, Zhou WJ, Gin DL (2001) Chem Mater 13:1949

    Article  CAS  Google Scholar 

  30. Boyer J, Corriu RJP, Perez R, Reye C (1983) Tetrahedron 39:117

    Article  CAS  Google Scholar 

  31. Kawai M, Onaka M, Izumi Y (1987) J Chem Soc Chem Commun 1203

  32. Ito S, Tanuma K, Matsuda K, Hayashi A, Komai H, Kubota Y, Asami M (2014) Tetraheron 70:8498

    Article  CAS  Google Scholar 

  33. Loh T-P, Li X-R (1999) Tetrahedron 55:10789

    Article  CAS  Google Scholar 

  34. Kalita P, Gupta NM, Kumar R (2011) Micropor Mesopor Mater 144:82

    Article  CAS  Google Scholar 

  35. Kalita P, Kumar R (2007) Stud Surf Sci Catal 170:1161

    Article  Google Scholar 

  36. Taralkar US, Kalita P, Kumar R, Joshi PN (2009) Appl Catal A Gen 358:88

    Article  CAS  Google Scholar 

  37. Gaydhankar TR, Joshi PN, Kalita P, Kumar R (2007) J Mol Catal A 265:306

    Article  CAS  Google Scholar 

  38. Garro R, Navarro MT, Primo J, Corma A (2005) J Catal 233:342

    Article  CAS  Google Scholar 

  39. Sasidharan M, Kumar R (1996) Catal Lett 38:251

    Article  CAS  Google Scholar 

  40. Sasidharan M, Raju SVN, Srinivasan KV, Paul V, Kumar R (1996) Chem Comm 129

  41. Sasidharan M, Kumar R (2003) J Catal 220:326

    Article  CAS  Google Scholar 

  42. Kalita P, Gupta NM, Kumar R (2007) J Catal 245:338

    Article  CAS  Google Scholar 

  43. Kalita P, Kumar R (2012) Micropor Mesopor Mater 149:1

    Article  CAS  Google Scholar 

  44. Kalita P, Kumar R (2012) Micropor Mesopor Mater 164:232

    Article  CAS  Google Scholar 

  45. Kalita P, Kumar R (2011) Appl Catal A Gen 397:250

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful to Prof. M. Deka, Head of Department, Applied Sciences, Gauhati University, Assam, India, for his constant support and encouragement. PKB is thankful to DST, Govt. of India for research funding (Grant No. SB/FT/CS-100/2012) under Fast Track Scheme.

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Correspondence to Pranjal K. Baruah or Pranjal Kalita.

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Baruah, P.K., Dutta, P. & Kalita, P. Cage Like Al-KIT-5 Mesoporous Materials for C–C Bond Formation Reactions Under Solvent Free Conditions. Catal Lett 145, 2037–2045 (2015). https://doi.org/10.1007/s10562-015-1611-7

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