Silica gel catalyzed highly selective C{single bond}S bond formation via Michael addition of thiols to α,β-unsaturated ketones under solvent-free conditions

Journal of Molecular Catalysis A: Chemical

Volumn 249, Issue 1-2, 2006, Pages 98-102

  Firouzabadi, Habib ^a   Iranpoor, Nasser ^a   Jafarpour, Maasoumeh ^a   Ghaderi, Arash ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

Heterogenenous catalyst; Michael addition; Silica gel; Solvent free; Thioether; Thiols

Indexed keywords

CATALYSIS; CATALYSTS; CHEMICAL BONDS; KETONES; ORGANIC SOLVENTS; SULFUR COMPOUNDS;

MICHAEL ADDITION; SOLVENT-FREE; THIOETHER; THIOLS;

SILICA GEL;

EID: 33645986513     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2006.01.004     Document Type: Article

References (27)

1. Diddams P., and Butters M. In: Smith K. (Ed). Solid Supports and Catalysts in Organic Synthesis (1992), Ellis Horwood and PTR Prentice Hall, New York and London (Chapters 1, 3 and 5)
2. For a review, see:
3. Banerjee A.K., Mimo M.S.L., and Vegas W.J.V. Russ. Chem. Rev. 70 (2001) 971
4. Chakraborti A.K., and Gulhane R. Tetrahedron Lett. 44 (2003) 3521
5. Chakraborti A.K., and Gulhane R. J. Chem. Soc. Chem. Commun. (2003) 1896-1897
6. Garg S.K., Kumar R., and Chakraborti A.K. Synlett (2005) 1370-1374
7. Chakraborti A.K., Rudrawar S., and Kondaskar A. Org. Biomol. Chem. 2 (2004) 1277
8. Kirk-Othmer Clark E. In: Kroschwitz J.I., and Howe-Grant M. (Eds). Encyclopedia of Chemical Technology. 4th ed. vol. 23 (1997), Wiley, New York 134-146
9. P.C.B. Page (Ed.), Organo-sulfur Chemistry I & II, Springer, Berlin, 1999.
10. Fujita E., and Nagao Y.J. Bioorg. Chem. (1977) 6287
11. A.L. Fluharty, in: S. Patai (Ed.), The Chemistry of Thiol Group, Wiley, New York, 1974, part 2, p. 589.
12. Sheldon R.A. Chirotechnologies, Industrial Synthesis of Optically Active Compounds (1993), Dekker Publishing, New York
13. Christoffers J. Eur. J. Org. Chem. (1998) 1259
14. Bandini M., Cozzi P.G., Giacomini M.G., Melchiorre P., Selva S., and Umani-Ronchi A. J. Org. Chem. 67 (2002) 3700
15. Srivastava N., and Banik B.K. J. Org. Chem. 68 (2003) 2109
16. Alam M.M., Varala R., and Adapa S.R. Tetrahedron Lett. 44 (2003) 5115
17. Ranu B.C., Dey S.S., and Samanta S. ARKIVOC (2005) 44
18. Garg S.K., Kumar R., and Chakraborti A.K. Tetrahedron Lett. 46 (2005) 1721
19. Hegedus L.L., and McCabe R.W. Catalyst Poisoning (1984), Marcel Dekker, New York
20. Hutton A.T. In: Wilkinson G., and McCleverty R.D. (Eds). Comprehensive Coordination Chemistry vol. 5 (1984), Pergamon, Oxford, UK 1151
21. Yadav J.S., Reddy B.V.S., and Baishya G. J. Org. Chem. 68 (2003) 2109
22. Ranu B.C., Dey S.S., and Hajra A. Tetrahedron 59 (2003) 2417
23. Firouzabadi H., Iranpoor N., and Jafari A.A. Adv. Synth. Catal. 347 (2005) 655
24. Firouzabadi H., Iranpoor N., and Jafari A.A. Synlett (2005) 299
25. Firouzabadi H., Iranpoor N., and Nowrouzi F. Chem. Commun. (2005) 789
26. Bakuzis P., and Bakuzis M.L.F. J. Org. Chem. 46 (1981) 235
27. Wabnitz T.C., and Spencer J.B. Org. Lett. 5 (2003) 2141