Polystyrene and silica gel supported AlCl3 as highly chemoselective heterogeneous Lewis acid catalysts for Friedel-Crafts sulfonylation of aromatic compounds

Catalysis Communications

Volumn 8, Issue 8, 2007, Pages 1191-1196

  Borujeni, Kaveh Parvanak ^a   Tamami, Bahman ^b  

^a SHAHREKORD UNIVERSITY   (Iran)

^b SHIRAZ UNIVERSITY   (Iran)

Author keywords

Aluminium chloride; Polystyrene; Silica gel; Sulfones; Sulfonylation

Indexed keywords

ALUMINUM COMPOUNDS; AROMATIC COMPOUNDS; CATALYSTS; CROSSLINKING; FRIEDEL-CRAFTS REACTION; SILICA GEL;

ALUMINIUM CHLORIDE; SULFONES; SULFONYLATION;

POLYSTYRENES;

EID: 34249278844     PISSN: 15667367     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.catcom.2006.10.028     Document Type: Article

References (24)

1. Ley S.V., Baxendale I.R., Bream R.N., Jackson P.S., Leach A.G., Longbottom D.A., Nesi M., Scott J.S., Storer R.I., and Taylor S.J. J. Chem. Soc. Perkin Trans. 1 (2000) 3815 and references cited therein
2. Akelah A., and Moet A. Functional Polymers and Their Applications (1990), John Wiley, New York
3. W.J. Michaely, G.W. Kraatz, US Patent 4780127, 1988 (CAN: 1989, 111, P 129017a).
4. Padwa A., Bullock W.H., and Dyszlewski A.D. J. Org. Chem. 55 (1990) 955
5. Blck E. Angew Chem. Int. Ed. Engl. 31 (1992) 1135
6. Mackinnon S.M., and Wang J.Y. Macromolecules 31 (1998) 7970
7. Jensen R., and Goldman G. In: Olah G. (Ed). Friedel-Crafts and Related Reactions vol. III (1964), Wiley Interscience, New York 1319-1367
8. Simpkins N.S. Sulfones in Organic Synthesis (1993), Pergamon Press, Oxford
9. Olah G.A., Kobayashi S., and Nishimura J. J. Am. Chem. Soc. 95 (1973) 564
10. Repichet S., Roux C.L., and Dubac J. Tetrahedron Lett. 40 (1999) 9233
11. Choudhary B.M., Chowdari N.S., and Kantam M.L. J. Chem. Soc. Perkin Trans. 1 (2000) 2689
12. Singh R.P., Kamble R.M., Chanda K.L., Saravanan P., and Singh V.K. Tetrahedron Lett. 57 (2001) 241
13. Frost C.G., Hartley J.P., and Whittle A.J. Synlett 6 (2001) 830
14. Olah G.A., Mathew T., and Prakash G.K. Chem. Commun. 17 (2001) 1696
15. Laidlaw P., Bethell D., Brown S.M., Watson G., Willock D.J., and Hutchings G.J. J. Mol. Catal. A: Chem. 178 (2002) 205
16. Garzya V., Forbes I.T., Lauru S., and Maragni P. Tetrahedron Lett. 45 (2004) 1499
17. Singh D.U., Singh P.R., and Samant S.D. Tetrahedron Lett. 45 (2004) 9079
18. Alexander M.V., Khandekar A.C., and Samant S.D. J. Mol. Catal. A: Chem. 223 (2004) 75
19. Tamami B., and Borujeni K.P. Synth. Commun. 33 (2003) 4253
20. Tamami B., and Borujeni K.P. Tetrahedron Lett. 45 (2004) 715
21. Tamami B., and Borujeni K.P. Synth. Commun. 34 (2004) 65
22. Borujeni K.P. Synth. Commun. 35 (2005) 2575
23. 1.0 g of solid catalyst was fused with Na metal, extracted with 10 ml of water and filtered. The aluminium and chloride content of the filtrate was determined by the Mohr titration method. For the procedure refer to:. Kolthoff I.M., and Sandell E.B. Textbook of Quantitative Inorganic Analysis. third ed. (1965), Macmillan Company, New York pp. 451, 542
24. Graybill B.M. J. Org. Chem. 32 (1967) 2931