Highly efficient tetrahydropyranylation of alcohols and phenols catalyzed by a new and reusable high-valent vanadium(IV) porphyrin

Comptes Rendus Chimie

Volumn 14, Issue 12, 2011, Pages 1095-1102

  Abdolmanaf Taghavi, S ^a   Moghadam, Majid ^a   Mohammadpoor Baltork, Iraj ^a   Tangestaninejad, Shahram ^a   Mirkhani, Valiollah ^a   Khosropour, Ahmad Reza ^a  

^a UNIVERSITY OF ISFAHAN   (Iran)

Author keywords

Alcohols; Electron deficient; Phenols; THP ether; Vanadium porphyrin

Indexed keywords

EID: 82455164272     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2011.09.009     Document Type: Article

References (61)

1. R. Ortiz de Montellano Cytochrome P-450, Structure, Mechanism and Biochemistry 2nd ed. 1995 Plenum Press New York
2. R. A. Sheldon, In B. Meunier (Ed), Biomimetic Oxidations Catalyzed by Transition Metal Complexes, Imperial College Press, London, 2000.
3. D. Mansuy Coord. Chem. Rev. 125 1993 129
4. J.T. Groves, Y. Watanabe, and T.J. McMurry J. Am. Chem. Soc. 105 1983 4489
5. J.P. Collman, J.I. Brauman, B. Meunier, and S.A. Raybuck Proc. Natl. Acad. Sci. USA 81 1984 3245
6. M.W. Grinstaff, M.G. Hill, E.R. Birnbaum, W.P. Schaefer, J.A. Labinger, and H.B. Gray Inorg. Chem. 34 1995 4896
7. M. Moghadam, I. Mohammadpoor-Baltork, S. Tangestaninejad, V. Mirkhani, H. Kargar, and N. Zeini-Isfahani Polyhedron 28 2009 3816
8. S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, and N. Hosseini J. Iran. Chem. Soc. 7 2010 663
9. K. Suda, M. Sashima, M. Izutsu, F. Hino, J. Chem. Soc., Chem. Commun. (1994) 949.
10. T. Takanami, R. Hirabe, M. Ueno, F. Hino, K. Suda, Chem. Lett. (1996) 1031.
11. T. Takanami, M. Hayashi, K. Iso, H. Nakamoto, and K. Suda Tetrahedron 62 2006 9467
12. T. Takanami, M. Hayashi, and K. Suda Tetrahedron Lett. 46 2005 2893
13. K. Suda, K. Baba, S. Nakajima, T. Takanami, Chem. Commun. (2002) 257.
14. K. Suda, K. Baba, S. Nakajima, and T. Takanami Tetrahedron Lett. 40 1999 7243
15. K. Suda, T. Kikkawa, S. Nakajima, and T. Takanami J. Am. Chem. Soc. 126 2004 9554
16. S. Tangestaninejad, M.H. Habibi, V. Mirkhani, and M. Moghadam Synth. Commun. 32 2002 1337
17. S. Tangestaninejad, M.H. Habibi, V. Mirkhani, M. Moghadam, J. Chem. Res. (S) (2001) 365.
18. M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, and R. Shaibani J. Mol. Catal. A: Chem. 219 2004 73
19. M. Moghadam, S. Tangestaninejad, V. Mirkhani, and R. Shaibani Tetrahedron 60 2004 6105
20. S. Gharaati, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, and F. Kosari Inorg. Chim. Acta. 363 2010 1995
21. M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, and S. Gharaati Appl. Organomet. Chem. 23 2009 446
22. S.A. Taghavi, M. Moghadam, I. Mohammadpoor-Baltork, S. Tangestaninejad, V. Mirkhani, A.R. Khosropour, and V. Ahmadi Polyhedron 30 2011 2244
23. M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, and S.A. Taghavi J. Mol. Catal. A: Chem. 274 2007 217
24. M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, and S.A. Taghavi Catal. Commun. 8 2007 2087
25. M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, and S. Gharaati Polyhedron 29 2010 212
26. M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, M. Khajehzadeh, F. Kosari, and M. Araghi Polyhedron 29 2010 238
27. M. Schelhaas, and H. Waldmann Angew. Chem. Int. Ed. Engl. 35 1996 2056
28. Y. Fukase, K. Fukase, and S. Kusumoto Tetrahedron Lett. 40 1999 1169
29. G. Sartori, R. Ballini, F. Bigi, G. Bosica, R. Maggi, and P. Righi Chem. Rev. 104 2004 199
30. T.W. Greene, and P.G.M. Wuts Protective Groups in Organic Synthesis 2nd ed. 1991 Wiley New York
31. P. J. Kocienski, Protective Groups; Enders, R., Noyori, R., Trost, B.M., Eds.; Thieme: Stuttgart (1994).
32. M. Miyashita, A. Yoshikoshi, and P.A. Grieco J. Org. Chem. 42 1977 3772
33. Y. Morizawa, I. Mori, T. Hiyama, H. Nozaki, Synthesis (1981) 899.
34. G. A. Olah, A. Husain, B.P. Singh, Synthesis (1985) 703.
35. U.T. Bhalerao, K. Joj Davis, and B. Vittal Rao Synth. Commun. 26 1996 3081
36. K. Tanemura, T. Horaguchi, and T. Suzuki Bull. Chem. Soc. Jpn. 65 1992 304
37. S. Ma, and L.M. Venanzi Tetrahedron Lett. 34 1993 5269
38. N. Deka, and J.C. Sarma J. Org. Chem. 66 2001 1947
39. V.V. Namboodiri, and R.S. Varma Tetrahedron Lett. 43 2002 1143
40. T. Mineno Tetrahedron Lett. 43 2002 7975
41. N. Rezai, F.A. Meybodi, and P. Salehi Synth. Commun. 30 2000 1799
42. M.H. Habibi, S. Tangestaninejad, I. Mohammadpoor-Baltork, V. Mirkhani, and B. Yadollahi Tetrahedron Lett. 42 2001 2851
43. L.C. Branco, and C.A.M. Afonso Tetrahedron 57 2001 4405
44. S. Naik, R. Gopinath, and B.K. Patel Tetrahedron Lett. 42 2001 7679
45. B. Karimi, and J. Maleki Tetrahedron Lett. 43 2002 5353
46. S. Hoyer, P. Laszlo, Synthesis (1986) 655.
47. B.C. Ranu, and M. Saha J. Org. Chem. 59 1994 8269
48. N. Ravindranath, C. Ramesh, B. Das, Synlett (2001) 1777.
49. B. Tamami, and K.P. Borujeny Tetrahedron Lett. 45 2004 715
50. B. Karimi, and M. Khalkhali J. Mol. Catal. A: Chem. 232 2005 113
51. K. Shimizu, E. Hayashi, T. Hatamachi, T. Kodama, and Y. Kitayama Tetrahedron Lett. 45 2004 5135
52. G.P. Romanelli, G. Baronetti, H.J. Thomas, and J.C. Autino Tetrahedron Lett. 43 2002 7589
53. Y.-G. Wang, X.-X. Wu, and Z.-Y. Jiang Tetrahedron Lett. 45 2004 2973
54. B.M. Choudary, V. Neeraja, and M.L. Kantam J. Mol. Catal. A: Chem. 175 2001 169
55. H. Alper, L. Dinkes, Synthesis (1972) 81.
56. M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, and S. Gharaati Inorg. Chim. Acta. 363 2010 1523
57. M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, and S. Gharaati J. Mol. Catal. A: Chem. 337 2011 95
58. I. Bertini, H.B. Gray, S.J. Lippard, and J.S. Valentine Bioinorganic Chemistry 1994 University Science Books Mill Valley, California
59. A.D. Adler, F.R. Longo, J.D. Finarelli, J. Goldmacher, J. Assour, and L. Korsakoff J. Org. Chem. 32 1976 476
60. S. Bencosme, M. Labady, and C. Romero Inorg. Chim. Acta. 123 1986 15
61. P. Richard, J.L. Poncet, J.M. Barbe, R. Guilard, J. Goulon, D. Rinaldi, A. Cartier, and Tola F P. Chem. Soc. Dalton Trans 1982 1451