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Document Type : Original Article

Authors

1 School of Chemical Sciences, SRTM University, Nanded, Maharashtra 431606, India

2 Materials Research Laboratory, Shrikrishna Mahavidyalaya, Gunjoti Maharashtra 413613, India

Abstract

The spinels of AB2O4 type display very interesting catalytic properties and have been shown to possess potential industrial applications . Especially spinels have been shown to be selective and active catalysts .Nano ZnFe2O4 ferrite synthesized by sol–gel auto-combustion method was found to be an efficient catalyst for acetylation of activated alcohols using acetic acid as reagent. A variety of activated alcohols undergo acetylation under the reaction conditions to afford the corresponding acetates in good yield. The salient features of this protocol include selectivity towards activated alcohols, use of cheap catalyst and environmentally benign protocol. The chemoselectivity of the protocol for activated systems making amines, phenols and other nucleophiles inert to the present reaction conditions makes this approach synthetically attractive and would supplement the many other protocols that are available.

Graphical Abstract

An Efficient Method for Chemoselective Acetylation of Activated Alcohols Using Nano ZnFe2O4 as Catalyst

Keywords

1. Ghorapade S.P., Darshane V.S., Dixit S.G.  Appl. Catal. A Gen., 1998,  166135
2. Hankare P.P., Sankpal U.B., Patil R.P., Lokhande P.D., Sasikala P. Mat. Sci. Eng. B, 2001, 176:103
3. Gill C.S., Long W., Jones C.W. Catal. Lett., 2009, 131:425
4. Senapati K., Borgohain C., Phukan P.  J. Mol. Catal .A Chem., 2011, 339:24
5. Jalowiecki L., Wrbel G., Daage M., Bonnelle J.P.  J. Catal., 1987, 107:375
6. Erran E., Trifiro F., Vaccari A., Richter M., Catal. Lett., 1989, 3:65
7. Chandrashekhar S., Ramachander T., Takhi M. Tetrahedron Lett., 1998, 39:3263
8. Toledo-Antonio J.A., Nava N., Martı´nez M., Bokhimi X. Appl. Catal. A., 2002, 234:137
9. Papa F., Patron L., Carp O., Paraschiv C., Ioan B.  J. Mol. Catal. A Chem ., 2009, 299:93
10. (a) Horton D. Organic Synthesis Collective, 1991, V:1-6 (b) Rana S.S., Barlow J.J., Matta K.L.  Tetrahedron Lett., 1981, 22:5007 (c) Monrsit A.A., Pujol H., Poupat C., Ahond A., Potier P. Tetrahedron Lett., 1996, 37:9189
11. Chauhan K.K., Frost C.G., Love I., Waite D. Synlett., 1999, 11:1743
12. Saravanan P., Singh V.K.  Tetrahedron Lett., 1999, 40:2611
13. Orita A., Tanahashi C., Kakuda A., Otera J. Angrew. Chem. Int. Ed., 2000, 39: 2877
14. Moghadam M., Tangestaninejad S., Mirkhani V., Mohammadpoor-Baltork I., Babghanbari M., Zarea L.  J. Iran. Chem. Soc., 2009, 6:523
15. Iranpoor N., Shekarrize M. Bull. Chem. Soc. Jpn., 1999, 72:455
16. Alleti R., Perambuduru M., Samantha S., Prakash V., Reddy V.P. J. Mol. Catal. A Chem., 2005, 226:57
17. Ishihara K., Kubota M., Kurihara H., Yamamoto H.  J. Am. Chem. Soc., 1995, 117:6639
18. Ishihara K., Kubota M., Kurihara H., Yamamoto H.  J. Org. Chem., 1996, 61:4560
19. Ishihara K , Kubota M , Yamamoto H.  Synlett., 1996, 3:265
20. Zhao H., Pendri A., Greenwald R.B.  J. Org. Chem., 1997, 63:7559
21. Procopiou P.A., Baugh S.P.D., Flack S.S., Inglis G.G.A.  J. Org. Chem., 1998, 63:2342
22. Procopiou P.A., Baugh S.P.D., Flack S.S., Inglis G.G.A.  J. Chem. Soc..Chem. Commun., 1996, 23:2625
23. Miyashita M., Shiina I., Miyoshi S., Mukaiyama T. Bull.Chem. Soc. Jpn., 1993, 66:1516
27. Nakae Y., Kusaki I., Sato T. Synlett., 2001, 10:1584
25.Bartoli G., Bosco M., Dalpozzo R., Marcantoni E., Massaccesi M., Rinaldi S., Sambri L. Synlett ., 2003, 1:39
26. Iqbal J., Srivastava R.R. J. Org. Chem., 1992, 57:2001
27. Phukan P.  Tetrahedron Lett., 2004, 45:4785
28. Nishiguchi T., Taya H.  J. Chem. Soc. Perkin. Trans., 1990, 1:172
29. Dewan A., Bora U., Kakati D. Bull. Korean. Chem. Soc., 2010, 31:3870
30. Barrett A.G., Braddock D.C. Chem. Commun., 1997, 4: 351
31. Heravi M.M., Behbahani F.K., Shoar R.H., Oskooie H.A. Catal. Commun., 2006, 31:136
32. Choudary B.M., Bhaskar V., Kantam M.L., Rao K.K., Raghavan K.V.  US, 2002, 6:472
33. Pushpaletha P. , Lalithambika M.  Appl. Clay. Sci., 2011, 31:424
34. Velusamy S., Borpuzari S., Punniyamurthy T. Tetrahedron, 2005, 21:2011
35. Osiglio L., Romanelli G., Blanco M. J. Mol .Catal. A. Chem, 2010, 316:52
36. Gowda S., Rai K.L.  J. Mol. Catal. A Chem., 2004, 217:27