Efficient synthesis of carbonyl compounds: Oxidation of azides and alcohols catalyzed by vanadium pentoxide in water using tert-butylhydroperoxide

Tetrahedron

Volumn 67, Issue 44, 2011, Pages 8544-8551

  Alagiri, Kaliyamoorthy ^a   Prabhu, Kandikere Ramaiah ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Alcohols; Azides; Carbonyl compounds; Oxidation; tert Butylhydroperoxide

Indexed keywords

ALCOHOL DERIVATIVE; AZIDE; CARBONYL DERIVATIVE; KETONE DERIVATIVE; TERT BUTYL HYDROPEROXIDE; VANADIUM PENTOXIDE;

ARTICLE; CATALYST; CHEMICAL REACTION; DRUG SYNTHESIS; ORGANIC CHEMISTRY; OXIDATION; PRIORITY JOURNAL;

EID: 80053260430     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.08.080     Document Type: Article

References (87)

1. M. Hudlicky Oxidations in Organic Chemistry 1990 ACS Monograph 186; American Chemical Society Washington, D.C.
2. R.A. Sheldon, and J.K. Kochi Metal-Catalyzed Oxidations of Organic Compounds 1981 Academic New York, NY
3. J.M. Cassady, S.R. Byrn, I.K. Stamos, S.M. Evans, and A. McKenzie J. Med. Chem. 21 1978 815
4. H.Y.P. Choo, K.H. Park, J. Peak, D.H. Kim, and H.S. Chung Eur. J. Med. Chem. 35 2000 643
5. R.C. Larock Comprehensive Organic Transformations 1999 WILEY-VCH Weinheim 1205
6. R. Stewart K.B. Wiberg, Oxidation in Organic Chemistry, Part A 1965 Academic New York, NY 47
7. D.G. Lee W.S. Trahanowky, Oxidation in Organic Chemistry, Part D 1982 Academic New York, NY 193
8. K.B. Sharpless, and K. Akashi J. Am. Chem. Soc. 97 1976 5927
9. J. March Advanced Organic Chemistry: Reactions, Mechanisms, and Structure 4 ed. 1992 John Wiley New York, NY
10. D.G. Lee, and U.A. Spitzer J. Org. Chem. 35 1970 3589
11. N. Jiang, and A.J. Ragauskas J. Org. Chem. 72 2007 7030 and references therein
12. B.M. Trost Science 254 1991 1471
13. R.A. Sheldon Green Chem. 2 2000 G1
14. P.T. Anastas, L.B. Bartlett, M.M. Kirchhoff, and T.C. Williamson Catal. Today 55 2000 11
15. T. Mallat, and A. Baiker Chem. Rev. 104 2004 3037
16. R.A. Sheldon, I.W.C.E. Arends, G.-J. Ten Brink, and A. Dijksman Acc. Chem. Res. 35 2002 774
17. I.W.C.E. Arends, and R.A. Sheldon Appl. Catal., A 212 2001 175
18. R. Gopinath, and B.K. Patel Org. Lett. 2 2000 577
19. Y. Ishii, S. Sakaguchi, and T. Iwahama Adv. Synth. Catal. 343 2001 393
20. A. Butler, M.J. Clague, and G.E. Meister Chem. Rev. 94 1994 625
21. D.B. Dess, and J.C. Martin J. Am. Chem. Soc. 113 1991 7277
22. J. Einhorn, C. Einhorn, F. Ratajczak, and J.L. Pierre J. Org. Chem. 61 1996 7452
23. L.D. Luca, G. Giacomelli, and A. Porcheddu Org. Lett. 3 2001 3041
24. K.B. Sharpless, and T. Katsuki J. Am. Chem. Soc. 102 1980 5974
25. R.W. Murray Chem. Rev. 89 1989 1187
26. M. Frohn, Z.X. Wang, and Y. Shi J. Org. Chem. 63 1998 6425
27. T. Hirao Chem. Rev. 97 1997 2707
28. T. Fukuyama, B. Vranesic, D.P. Negri, and Y. Kishi Tetrahedron Lett. 31 1978 2741
29. M. Hashimoto, T. Kan, M. Yanagiya, H. Shirahama, and T. Matsumoto Tetrahedron Lett. 28 1987 5665
30. A. Blanc, and F.D. Toste Angew. Chem., Int. Ed. 45 2006 2096
31. N. Murase, Y. Hoshino, M. Oishi, and H. Yamamoto J. Org. Chem. 64 1999 338
32. S. Velusamy, and T. Punniyamurthy Org. Lett. 6 2004 217
33. K. Kaneda, Y. Kawanishi, K. Jitsukawa, and S. Teranishi Tetrahedron Lett. 24 1983 5009
34. J. Sun, C. Zhu, Z. Dai, M. Yang, Y. Pan, and H. Hu J. Org. Chem. 69 2004 8500
35. L. Rout, and T. Punniyamurthy Adv. Synth. Catal. 347 2005 1958
36. R.C. Michaelson, R.E. Palermo, and K.B. Sharpless J. Am. Chem. Soc. 99 1977 1990
37. M. Maddani, and K.R. Prabhu Tetrahedron Lett. 49 2008 4526
38. M. Maddani, S.R.K. Moorthy, and K.R. Prabhu Tetrahedron 66 2010 329
39. M. Maddani, and K.R. Prabhu J. Chem. Sci. 90 2010 287
40. M. Lamani, and K.R. Prabhu Angew. Chem., Int. Ed. 49 2010 6622
41. M. Maddani, and K.R. Prabhu J. Org. Chem. 75 2010 2327
42. B.B. Jarvis, and P.E. Nicholas J. Org. Chem. 44 1979 2951
43. R. Sasson, and S. Rozen Org. Lett. 7 2005 2177
44. S. Rozen, and M. Carmeli J. Am. Chem. Soc. 125 2003 8118
45. B.A. Belinka, and A. Hassner Jr. J. Org. Chem. 43 1979 4712
46. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004
47. S. Brase, C. Gil, K. Knepper, and V. Zimmermann Angew. Chem., Int. Ed. 44 2005 5188
48. H. Bortels Arch. Mikrobiol. 1 1930 333
49. D.C. Rees Annu. Rev. Biochem. 71 2002 221
50. P.C. Dos Santos, R.Y. Igarashi, H.-N. Lee, B.M. Hoffman, L.C. Seefeldt, and D.R. Dean Acc. Chem. Res. 38 2005 208 and references therein
51. H. Enemark, J.J.A. Cooney, J.J. Wang, and R.H. Holm Chem. Rev. 104 2004 1175
52. G.L. Wilson, R.J. Greenwood, J.R. Pilbrow, J.T. Spence, and A.G. Wedd J. Am. Chem. Soc. 113 1991 6803
53. R.L. Robson, R.R. Eady, T.H. Richardson, R.W. Miller, M. Hawkins, and J.R. Postage Nature 322 1986 388
54. R.N. Pau M.J. Dilworth, A.R. Glenn, Biology and Biochemistry of Nitrogen Fixation 1991 Elsevier Amsterdam Chapter 3
55. D. Rehder Coord. Chem. Rev. 182 1999 297
56. K.H. Thompson, and C. Orvig Coord. Chem. Rev. 219 2001 1033
57. A.G.J. Ligtenbarg, R. Hage, and B.L. Feringa Coord. Chem. Rev. 237 2003 89
58. M. Hidai, and Y. Mizobe Can. J. Chem. 83 2005 358
59. P.V. Chouthaiwale, G.H. Suryavanshi, and A. Sudalai Tetrahedron Lett. 49 2008 6401
60. C. Viuf, and M. Bols Angew. Chem., Int. Ed. 40 2001 623
61. M. Baruah, and M. Bols Synlett 2002 1111
62. L.G. Marinescu, C.M. Pedersen, and M. Bols Tetrahedron 61 2005 123
63. T.L. Amyes, and J.P. Richard J. Chem. Soc., Chem. Commun. 1991 200
64. R. Ghorbani-Vaghei, M. Chegini, H. Veisi, and M. Karimi-Taber Tetrahedron Lett. 50 2009 1861 and references therein
65. A.V. Malkov, L. Czemerys, and D.A. Malyshev J. Org. Chem. 74 2009 3350
66. A.T. Khan, and P. Goswami Tetrahedron Lett. 46 2005 4937
67. Oxidation of alcohols in water furnished the corresponding acid exclusively and ester was not observed. Whereas, the same reaction in MeOH furnished corresponding methyl ester in minor amount (18%) along with the corresponding acid and aldehyde in 67% and 10 % yields, respectively.
68. M. Zhao, J. Li, E. Mano, Z. Song, D.M. Tschaen, E.J.J. Grabowski, and P.J. Reider J. Org. Chem. 64 1999 2564
69. R. Mazitschek, M. Mulbaier, and A. Giannis Angew. Chem., Int. Ed. 41 2002 4059
70. E. Dalcanale J. Org. Chem. 51 1986 567
71. A. Al-Hunaiti, T. Niemi, A. Sibaouih, P. Pihko, M. Leskela, and T. Repo Chem. Commun. 2010 9250
72. J.M. Khurana, P. Sharma, A. Gogia, and B.M. Kandpal Org. Prep. Proced. Int. 39 2007 185
73. C. Venturello, and M. Ricci J. Org. Chem. 51 1986 1599
74. M. Trincado, H. Gruetzmacher, F. Vizza, and C. Bianchini Chem. - Eur. J. 16 2010 2751
75. X.Q. Li, W.K. Wang, and C. Zhang Adv. Synth. Catal. 351 2009 2342
76. J. Wegner, S. Ceylan, C. Friese, and A. Kirschning Eur. J. Org. Chem. 23 2010 4372
77. T. Dohi, N. Takenaga, A. Goto, H. Fujioka, and Y. Kita J. Org. Chem. 73 2008 7365
78. V. Nair, V. Varghese, R.R. Paul, A. Jose, C.R. Sinu, and R.S. Menon Org. Lett. 12 2010 2653
79. M. Uyanik, R. Fukatsu, and K. Ishihara Chem. - Asian J. 5 2010 456
80. A.R. Hajipour, K. Karami, and A. Pirisedigh Appl. Organomet. Chem. 2 2010 454
81. K.M. Lakshmi, R. Arundhathi, P.R. Likhar, and D. Damodara Adv. Synth. Catal. 351 2009 2633
82. R.G. Shotter, and K.M. Johnston Tetrahedron 29 1973 2163
83. D. Seyferth, and R.J. Spohn J. Am. Chem. Soc. 90 1968 540
84. S. Yamazaki Org. Lett. 1 1999 2129
85. I.A. Pearl, and D.L. Beyer J. Am. Chem. Soc. 74 1952 4263
86. J.J. Looker J. Org. Chem. 36 1971 2681
87. K. Yanada, R. Yanada, and H. Meguri J. Chem. Soc., Chem. Commun. 1990 730