Samarium trifluoromethanesulfonate: An efficient moisture tolerant acylation catalyst under solvent-free condition

Journal of Carbohydrate Chemistry

Volumn 27, Issue 1, 2008, Pages 1-9

  Roy, Bimalendu ^a   Dasgupta, Somnath ^a   Kumar Rajput, Vishal ^a   Mukhopadhyay, Balaram ^a,b  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

^b INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH KOLKATA   (India)

Author keywords

Acylation; Solvent free; Sugar acetates

Indexed keywords

EID: 45949112127     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328300801991245     Document Type: Article

References (22)

1. Greene, T.W.; Wuts, P.G.M. Protecting Groups in Organic Synthesis, 3rd Edn.; John Wiley and Sons: New York, 1999.
2. 3. J. Org. Chem. 2004, 69, 577-580;
3. (b) Nafion-H: Kumareswaran, R.; Pachamuthu, K.; Vankar, Y.D. nafion-h catalyzed acetylation of alcohols. Synlett. 2000, 1652-1654;
4. 2Cl: Salavati-Niasari, M.; Hydrazadeh, S.; Amiri, A.; Salavati, S. Manganese(III) bis(2-hydroxyanil)acetylacetonato complex as effective catalyst for acylation of alcohols, amines and phenols with acetic anhydride. J. Mol. Catal. A 2005, 231, 191-195;
5. 2: Chen, C.-T.; Kuo, J.-H.; Pawar, V.D.; Munot, Y.S.; Weng, S.-S.; Ku, C.-H.; Liu, C.-Y. Nucleophilic acyl substitutions of anhydrides with protic nucleophiles catalyzed by amphoteric, oxomolybdenum species. J. Org. Chem. 2005, 70, 1188-1197;
6. 2: Mukhopadhyay, B.; Kartha, K.P.R.; Russell, D.A.; Field, R.A. Streamlined synthesis of per-O-acetylated sugars, glycosyl iodides, or thioglycosides from unprotected reducing sugars. J. Org. Chem. 2004, 69, 7758-7760;
7. 3 generated in situ from the procatalyst BiOCl and acetyl chloride. Tetrahedron Lett. 2004, 45, 6775-6778;
8. 2 functional groups in the absence of solvent at room temperature. Chem. Commun. 2003, 764-765;
9. 3: De, S.K. Ruthenium(III) chloride catalyzed acylation of alcohols, phenols, thiols, and amines. Tetrahedron Lett. 2004, 45, 2919-2922;
10. (i) Ionic liquid: Forsyth, S.A.; MacFarlane, D.R.; Thompson, R.J.; Itzstein, M.V. Rapid, clean, and mild O-acetylation of alcohols and carbohydrates in an ionic liquid. Chem. Commun. 2002, 714-715;
11. 2·6H2O as a powerful catalyst for a practical acylation of alcohols with acid anhydrides. Eur. J. Org. Chem. 2003, 4611-4617;
12. 4-silica: Chakraborti, A.K.; Gulhane, R. Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines. Chem. Commun. 2003, 1896-1897;
13. 4-silica: Chakraborti, A.K.; Gulhane, R. Fluoroboric acid adsorbed on silica gel as a new and efficient catalyst for acylation of phenols, thiols, alcohols, and amines. Tetrahedron Lett. 2003, 44, 3521-3525.
14. For a review on rare-earth metal triflates see: Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W.-L. Rare-earth metal triflates in organic synthesis. Chem. Rev. 2002, 102, 2227-2302.
15. Chauhan, K.K.; Frost, C.G.; Love, I.; Waite, D. Indium triflate: an efficient catalyst for acylation reactions. Synlett. 1999, 1743-1744.
16. 3. J. Org. Chem. 2001, 66, 8926-8934.
17. Dalpozzo, R.; De Nino, A.; Maiuolo, L.; Procopio, A.; Nardi, M.; Bartoli, G.; Romeo, R. Highly efficient and versatile acetylation of alcohols catalyzed by cerium (III) triflate. Tetrahedron Lett. 2003, 44, 5621-5624.
18. Procopio, A.; Dalpozzo, R.; De Nino, A.; Maiuolo, L.; Russo, B.; Sindona, G. Erbium (III) triflate as an extremely active acylation catalyst. Adv. Synth. Catal. 2005, 346, 1465-1470.
19. Karimi, B.; Maleki, J. Lithium trifluoromethanesulfonate (LiOTf) as a recyclable catalyst for highly efficient acetylation of alcohols and diacetylation of aldehydes under mild and neutral reaction conditions. J. Org. Chem. 2003, 68, 4951-4954.
20. Chandra, K.L.; Saravanan, P.; Singh, R.K.; Singh, V.K. Lewis acid catalyzed acylation reactions: scope and limitations. Tetrahedron 2002, 58, 1369-1374.
21. 2-catalyzed preparation of per-O-acetylated hexopyranoses with stoichiometric acetic anhydride and sequential one-pot anomeric substitution to thioglycosides under solvent-free conditions. J. Org. Chem. 2003, 68, 8719-8722.
22. Kobayashi, S.; Hachiya, I. Lanthanide triflates as water-tolerant Lewis acids. Activation of commercial formaldehyde solution and use in the aldol reaction of silyl enol ethers with aldehydes in aqueous media. J. Org. Chem. 1994, 59, 3590-3596.