Polymer-supported gadolinium triflate as a convenient and efficient Lewis acid catalyst for acetylation of alcohols and phenols

Tetrahedron Letters

Volumn 49, Issue 19, 2008, Pages 3165-3171

  Yoon, Hyo Jin ^a   Lee, Sang Myung ^a   Kim, Jong Ho ^a   Cho, Hong Jun ^a   Choi, Jung Woo ^a   Lee, Sang Hyeup ^b   Lee, Yoon Sik ^a  

^a Seoul National University   (South Korea)

^b Catholic University of Daegu   (South Korea)

Author keywords

Acetylation; Gadolinium triflate; Lewis acid catalyst; Polymer supported catalyst

Indexed keywords

ACETIC ANHYDRIDE; ALCOHOL DERIVATIVE; CHLOROFORM; CHLOROMETHYL POLYSTYRENE; DIMETHYL SULFOXIDE; DIOXANE; ETHER; GADOLINIUM; HEXANE; IMIDAZOLE DERIVATIVE; LEWIS ACID; PHENOL DERIVATIVE; POLYMER; POLYSTYRENE DERIVATIVE; RESIN; TOLUENE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; ATOMIC EMISSION SPECTROMETRY; CATALYST; CHEMICAL STRUCTURE; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; PROTON TRANSPORT; ROENTGEN SPECTROSCOPY; SCANNING ELECTRON MICROSCOPY;

EID: 41649090535     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.005     Document Type: Article

References (50)

1. Green T.W., and Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. (1999), John Wiley & Sons, New York p 150
2. Pearson A.L. WJ Handbook or Reagents for Organic Synthesis: Acetylationg Agents and Protecting Groups (1999), John Wiley, UK p 9
3. Larock R.C. Comprehensive Organic Transformations (1989), VCH, New York p 980
4. Sartori G., Ballini R., Bigi F., Bosica G., Maggi R., and Righi P. Chem. Rev. (2004) 199-250
5. DMAP (4-(dimethylamino)pyridine):. Hofle G., Steglich W., and Vorbrüggen H. Angew. Chem., Int. Ed. Engl. 17 (1978) 569
6. Pyridine:. Tomohumi S., Kousaburo O., and Takeshi O. Synthesis (1999) 1141
7. Tributylphosphine:. Vedejs E., and Diver S.T. J. Am. Chem. Soc. 115 (1993) 3358
8. PPY (4-pyrrolidinopyridine):. Scriven E.F.V. Chem. Soc. Rev. 12 (1983) 129
9. TEA (Triethylamine):. Zhdanov R.I., and Zhenodarova S.M. Synthesis (1975) 222
10. Cope A.C., and Herrick E.C. Organic Syntheses Collective Vol. IV (1963), Wiley, New York p 304
11. 3:. De S.K. Tetrahedron Lett. 45 (2004) 2919
12. 3:. Chakraborti A., and Gulhane R. Tetrahedron Lett. 44 (2003) 3521
13. 2:. Bosco J.W.J., and Saikia A.K. Chem. Commun. (2004) 1116
14. 2:. Iqbal J., and Srivastava R.R. J. Org. Chem. 57 (1992) 2001
15. 5:. Chandrasekhar S., Ramchander T., and Takhi M. Tetrahedron Lett. 39 (1998) 3263
16. 2:. Ishihara K., Ohara S., and Yamamoto H. Science 290 (2000) 1140
17. 4:. Chakroborti A.K., and Gulhane R. Synlett (2004) 627
18. 2:. Baker R.H., and Bordwell F.G. Org. Synth. 3 (1955) 141
19. 3:. Torregiani E., Seu G., Minassi A., and Appendino G. Tetrahedron Lett. 46 (2005) 2193
20. 2:. Ishii Y., Takeno M., Kawasaki Y., Muromachi A., Nishiyama Y., and Sakaguchi S. J. Org. Chem. 61 (1996) 3088
21. 5:. Yadav J.S., Narsaiah A.V., Reddy B.V.S., Basak A.K., and Nagaiah K. J. Mol. Catal. A: Chem. 230 (2005) 107
22. 3:. Ishihara K., Kubota M., Kurihara H., and Yamamoto H. J. Am. Chem. Soc. 117 (1995) 4413
23. 3:. Orita A., Tanahashi C., Kakuda A., and Otera J. Angew. Chem., Int. Ed. 39 (2000) 2877
24. 3:. Chauhan K.K., Frost C.G., Love I., and Waite D. Synlett (1999) 1743
25. 3:. Barrett A.G.M., and Braddock D.C. Chem. Commun. (1997) 351
26. 3SiOTf:. Procopiou P.A., Baugh S.P.D., Flack S.S., and Inglis G.G.A. Chem. Commun. (1996) 2625
27. 3:. Ishihara K., Kubota M., and Yamamoto H. Synlett (1996) 265
28. 3:. Mukaiyama T., Shiina I., and Miyashita M. Chem. Lett. (1992) 625
29. 2:. Saravanan P., and Singh V.K. Tetrahedron Lett. 40 (1999) 2611
30. LiOTf:. Karimi B., and Maleki J. J. Org. Chem. 68 (2003) 4951
31. 3:. Kamal A., Khan M.N.A., Reddy K.S., Srikanth Y.V.V., and Krishnaji T. Tetrahedron Lett. 48 (2007) 3813
32. Rare-earth metal:. Luo S., Zhu L., Talukdar A., Zhang G., Mi X., Cheng J.-P., and Wang P.G. Mini-Rev. Org. Chem. 2 (2005) 177
33. 4:. Nakae Y., Kusaki I., and Sato T. Synlett (2001) 1584
34. 2:. Bartoli G., Bosco M., Dalpozzo R., Marcantoni E., Massaccesi M., Rinaldi S., and Sambri L. Synlett (2003) 39
35. Molecular iodine:. Phukan P. Tetrahedron Lett. 45 (2004) 4785
36. 3-Nitrobenzeneboronic acid:. Tale R.H., and Adude R.N. Tetrahedton Lett. 47 (2006) 7263
37. 2O:. Reddy T.S., Narasimhulu M., Suryakiran N., Mahesh K.C., Ashalatha K., and Venkateswarlu Y. Tetrahedron Lett. 47 (2006) 6825
38. Zeolites:. Ballini R., Bosica G., Carloni S., Ciaralli L., Maggi R., and Sartori G. Tetrahedron Lett. 39 (1998) 6049
39. Clays:. Li A.-X., Li T.-S., and Ding T.-H. Chem. Commun. (1997) 1389
40. Montmorillonite K-10:. Damen E.W.P., Braamer L., and Scheeren H.W. Tetrahedron Lett. 39 (1998) 6081
41. Al-MCM-41:. Bhattacharyya K.G., Talukdar A.K., Das P., and Sivasanker S. Catal. Commun. 2 (2001) 105
42. Nafion-H:. Kumareswaran R., Pachamuthu K., and Vankar Y.D. Synlett (2000) 1652
43. 4:. Das B., and Thirupathi P. J. Mol. Catal. A: Chem. 269 (2007) 12
44. Kobayashi S., and Hachiya I. J. Org. Chem. 59 (1994) 3590
45. Kobayashi S. Synlett (1994) 689
46. Kobayashi S., and Ogawa C. Chem. Eur. J. 59 (2006) 3590
47. Alleti R., Perambuduru M., Samantha S., and Reddy V.P. J. Mol. Catal. A: Chem. 226 (2005) 57
48. Alleti R., Oh W.S., Perambuduru M., Afrasiabi Z., Sinn E., and Reddy V.P. Green Chem. 7 (2005) 203
49. Byun J.-W., and Lee Y.-S. Tetrahedron Lett. 45 (2004) 1837
50. -1 became stronger after immobilization of palladium. Also, the surface morphology of the catalyst was characterized by field emission scanning electron microscope (FE-SEM). There is no difference between before immobilization of gadolinium triflate and after.