Fluoroboric acid adsorbed on silica gel as a new and efficient catalyst for acylation of phenols, thiols, alcohols, and amines

Tetrahedron Letters

Volumn 44, Issue 17, 2003, Pages 3521-3525

  Chakraborti, Asit K ^a   Gulhane, Rajesh ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; BORIC ACID; FLUOROBORIC ACID; PHENOL DERIVATIVE; SILICA GEL; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ADSORPTION; ARTICLE; CATALYST; CHEMICAL STRUCTURE; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOSPECIFICITY; STOICHIOMETRY;

EID: 0037459871     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00683-X     Document Type: Article

References (34)

1. Greene T.W., Wuts P.G.M. Protective Groups in Organic Synthesis. 1999;Wiley, New York.
2. Hanson J.R. Protective Groups in Organic Synthesis. 1999;Blackwell Science Inc, Malden, MA.
3. Chakraborti A.K., Nayak M.K., Sharma L. J. Org. Chem. 67:2002;1776-1780.
4. Chakraborti A.K., Nayak M.K., Sharma L. J. Org. Chem. 67:2002;2541-2547.
5. Chakraborti A.K., Sharma L., Sharma U. Tetrahedron. 57:2001;9343-9346.
6. Chakraborti A.K., Nayak M.K., Sharma L. J. Org. Chem. 64:1999;8027-8030.
7. Steglich W., Hofle G. Angew. Chem., Int. Ed. Engl. 8:1969;981.
8. Vedjes E., Diver T.S. J. Am. Chem. Soc. 115:1993;3358-3359.
9. Iqbal J., Srivastava R. J. Org. Chem. 57:1992;2001-2007.
10. Ahmed S., Iqbal J. Tetrahedron Lett. 27:1986;3791-3794.
11. Ishihara K., Kubota M., Kurihara H., Yamamoto H. J. Am. Chem. Soc. 117:1995;4413-4414.
12. Ishihara K., Kubota M., Kurihara H., Yamamoto H. J. Org. Chem. 61:1996;4560-4567.
13. Ishihara K., Kubota M., Yamamoto H. Synlett. 1996;265-266.
14. Procopiou P.A., Baugh S.P.D., Flack S.S., Inglis G.G.A. J. Org. Chem. 63:1998;2342-2347.
15. Procopiou P.A., Baugh S.P.D., Flack S.S., Inglis G.G.A. Chem. Commun. 1996;2625-2626.
16. Orita A., Tanahashi C., Kakuda A., Otera J. Angew. Chem., Int. Ed. Engl. 39:2000;2877-2879.
17. Orita A., Tanahashi C., Kakuda A., Otera J. J. Org. Chem. 66:2001;8926-8934.
18. Carrigan M.D., Freiberg D.A., Smith R.C., Zerth H.M., Mohan R.S. Synthesis. 2001;2091-2093.
19. Saravanan P., Singh V.K. Tetrahedron Lett. 40:1999;2611-2614.
20. Chauhan K.K., Frost C.G., Love I., Waite D. Synlett. 1999;1743-1744.
21. Chandrasekhar S., Ramachander T., Takhi M. Tetrahedron Lett. 39:1998;3263-3266.
22. Ballini R., Bosica G., Carloni S., Ciaralli L., Maggi R., Sartori G. Tetrahedron Lett. 39:1998;6049-6052.
23. Li A.-X., Li T.-S., Ding T.-H. Chem. Commun. 1997;1389-1390.
24. Kumareswaran R., Pachamuthu K., Vankar Y.D. Synlett. 2000;1652-1654.
25. Kumar P., Pandey R.K., Bodas M.S., Dongare M.K. Synlett. 2001;206-209.
26. Nakae Y., Kusaki I., Sato T. Synlett. 2001;1584-1586.
27. Reaction with 4-hydroxybenzaldehyde resulted in a mixture of 4-acetoxybenzaldehyde, 4-hydroxybenzaldehyde-1,1-diacetate, and 4-acetoxybenzaldehyde-1,1-diacetate.
28. Harrowven D.C., Dainty R.F. Tetrahedron Lett. 37:1996;7659-7660.
29. Olah G.A., Prakash G.K.S. Superacids. 1985;Wiley, New York.
30. 4 (200 g, 3.6).
31. 4 (1).
32. 4 (room temperature).
33. 4 (no solvent is required).
34. Garrett, R. L. In Designing Safer Chemicals; Garrett, R. L.; De Vito, S. C., Eds.; American Chemical Society Symposium Series 640: Washington DC, 1996; Chapter 1.