A simple and convenient method for preparation of carboxylic acid alkyl esters, phenolic and thioesters using chlorodiphenylphosphine/I2 and imidazole reagent system

Tetrahedron

Volumn 66, Issue 50, 2010, Pages 9596-9601

  Nowrouzi, Najmeh ^a   Mehranpour, Abdol Mohammad ^a   Rad, Javad Ameri ^a  

^a PERSIAN GULF UNIVERSITY   (Iran)

Author keywords

Alkyl esters; Chlorodiphenylphosphine; Esterification; Iodine; Phenolic esters; Thioesters

Indexed keywords

ACETONITRILE; ALCOHOL DERIVATIVE; BENZOIC ACID; BENZYL BENZOATE; CARBOXYLIC ACID; ESTER; IMIDAZOLE; IODINE; PHENOL; PHOSPHINE; PHOSPHORUS; THIOESTER;

ARTICLE; BENZYLATION; ESTERIFICATION; POLYMERIZATION; PRIORITY JOURNAL; PURIFICATION; REACTION OPTIMIZATION; SOLVENT EFFECT; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 78449231580     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.10.022     Document Type: Article

References (40)

1. J. Otera Esterification Methods. Reactions and Applications 2003 Wiley-VCH Weinheim, Germany
2. R.C. Larock Comprehensive Organic Transformations 2nd ed. 1999 VCH New York, NY
3. M.L.M. Fernandes, E. Bolzani Saad, J.A. Meira, L.P. Ramos, D.A. Mitchell, and N. Krieger J. Mol. Catal. B 44 2007 8
4. Y. Liu, E. Lotero, and J.G. Goodwin J. Catal. 243 2006 221
5. S.L. Barbosa, M.J. Dabdoub, G.R. Hurtado, S.I. Klein, A.C.M. Baroni, and C. Cunha Appl. Catal., A 313 2006 146
6. W.B. Pan, F.R. Chang, L.M. Wei, M.J. Wu, and Y.C. Wu Tetrahedron Lett. 44 2003 331
7. K. Mohammed Khan, G.M. Maharvi, S. Hayat, Z. Ullah, M.L. Choudhary, and A. Rahman Tetrahedron 59 2003 5549
8. K. Ramalinga, P. Vijayalakshmi, and T.N.B. Kaimal Tetrahedron Lett. 43 2002 879
9. H. Vorbrüggen Synlett 11 2008 1603
10. A. Parenty, X. Moreau, and J.M. Campagne Chem. Rev. 106 2006 911
11. M. Nahmany, and A. Melman Org. Biomol. Chem. 2 2004 1563
12. T. Seki, T. Nakajo, and M. Onaka Chem. Lett. 35 2006 824
13. A. Chighine, S. Crosignani, M.C. Arnal, M. Bradley, and B. Linclau J. Org. Chem. 74 2009 4753
14. O. Mitsunobu, M. Yamada, and T. Mukaiyama Bull. Chem. Soc. Jpn. 40 1967 935
15. O. Mitsunobu, and M. Eguchi Bull. Chem. Soc. Jpn. 44 1971 3427
16. N. Iranpoor, H. Firouzabadi, D. Khalili, and S. Motevalli J. Org. Chem. 73 2008 4882
17. C. Salome, and H. Kohn Tetrahedron 65 2009 456
18. T. Shintou, W. Kikuchi, and T. Mukaiyama Bull. Chem. Soc. Jpn. 76 2003 1645
19. T. Mukaiyama, T. Shintou, and K. Fukumoto J. Am. Chem. Soc. 125 2003 10538
20. S. Dandapani, and D.P. Curran Chem. - Eur. J. 10 2004 3130
21. R. Dembinski Eur. J. Org. Chem. 2004 2763
22. A.R. Tunoori, D. Dutta, and G.I. Georg Tetrahedron Lett. 39 1998 8751
23. M.E. Lizarzaburu, and S.J. Shuttleworth Tetrahedron Lett. 44 2003 4873
24. R.G. Gentles, D. Wodka, D.C. Park, and A. Vasudevan J. Comb. Chem. 4 2002 442
25. M.K.W. Choi, H.S. He, and P.H. Toy J. Org. Chem. 68 2003 9831
26. P. Wentworth, A.M. Vandersteen, and K.D. Janda Chem. Commun. 1997 759
27. T.J. Dickerson, N.N. Reed, and K.D. Janda Chem. Rev. 102 2002 3325
28. R.A. Amos, R.W. Emblidge, and N. Havens J. Org. Chem. 48 1983 3598
29. D. Camp, and I.D. Jenkins Aust. J. Chem. 41 1988 1835
30. M. Von Itzstein, and M. Mocerino Synth. Commun. 20 1990 2049
31. N. Iranpoor, H. Firouzabadi, A. Jamalian, and F. Kazemi Tetrahedron 61 2005 5699
32. N. Iranpoor, H. Firouzabadi, and A. Jamalian Tetrahedron Lett. 46 2005 7963
33. N. Iranpoor, H. Firouzabadi, and A. Jamalian Tetrahedron 62 2006 1823
34. A.G.M. Barrett, D.C. Braddock, R.A. James, N. Koike, and P.A. Procopiou J. Org. Chem. 63 1998 6273
35. K. Kabuto, M. Imuta, E.S. Kempner, and H. Ziffer J. Org. Chem. 43 1978 2357
36. F. Cavelier, J. Daunis, and R. Jacquier Bull. Soc. Chim. Fr. 127 1990 210
37. E.J. Corey, and M.G. Bock Tetrahedron Lett. 16 1975 2643
38. K.L. Agarwal, M. Fridkin, E. Jay, and H.G. Khorana J. Am. Chem. Soc. 95 1973 2020
39. Y. Hu, W. Pa, W. Cui, and J. Wang Synth. Commun. 22 1992 2763
40. www.chemfinder.com