Hypervalent iodine oxidation of phenol derivatives using a catalytic amount of 4-iodophenoxyacetic acid and Oxone® as a co-oxidant

Tetrahedron

Volumn 66, Issue 31, 2010, Pages 5833-5840

  Yakura, Takayuki ^a   Omoto, Masanori ^a   Yamauchi, Yu ^a   Tian, Yuan ^a   Ozono, Ayaka ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

4 Iodophenoxyacetic acid; Hypervalent iodine; Oxidation; Oxone; Phenol

Indexed keywords

4 IODOPHENOXYACETIC ACID; BLATTELLAQUINONE; DIOXANE; PHENOL DERIVATIVE; PHENOXYACETIC ACID DERIVATIVE; QUINONE DERIVATIVE; SODIUM PEROXIDE; TETRAHYDROFURAN; UNCLASSIFIED DRUG; WATER;

ARTICLE; BLATTA GERMANICA; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COCKROACH; NONHUMAN; OXIDATION; PRIORITY JOURNAL; SYNTHESIS;

BLATTELLA GERMANICA;

EID: 77955466056     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.124     Document Type: Article

References (112)

1. P.J. Stang, and V.V. Zhdankin Chem. Rev. 96 1996 1123 1178
2. Y. Kita, T. Takada, and H. Tohma Pure Appl. Chem. 68 1996 627 630
3. T. Kitamura, and Y. Fujiwara Org. Prep. Proced. Int. 29 1997 409 458
4. A. Varvoglis, Hypervalent Iodine in Organic Synthesis 1996 Academic San Diego
5. A. Varvoglis Tetrahedron 53 1997 1179 1255
6. V.V. Zhdankin Rev. Heteroatom Chem. 17 1997 133 151
7. T. Muraki, H. Togo, and M. Yokoyama Rev. Heteroatom Chem. 17 1997 213 243
8. A. Varvoglis, and S. Spyroudis Synlett 1998 221 232
9. T. Wirth, and U.H. Hirt Synthesis 1999 1271 1287
10. M. Ochiai K. Akiba, Chemistry of Hypervalent Compounds 1999 Wiley-VCH New York, NY Chapter 12
11. T. Wirth Angew. Chem., Int. Ed. 40 2001 2812 2814
12. V.V. Zhdankin, and P.J. Stang Chem. Rev. 102 2002 2523 2584
13. T. Wirth, Hypervalent Iodine Chemistry 2003 Springer Berlin, Heidelberg
14. T. Wirth Angew. Chem., Int. Ed. 44 2005 3656 3665
15. R.M. Moriarty J. Org. Chem. 70 2005 2893 2903
16. T. Dohi, and Y. Kita Kagaku (Kyoto, Japan) 61 2006 68 69
17. R.D. Richardson, and T. Wirth Angew. Chem., Int. Ed. 45 2006 4402 4404
18. M. Ochiai, and K. Miyamoto Eur. J. Org. Chem. 2008 4229 4239
19. T. Dohi, and Y. Kita Chem. Commun. 2009 2073 2085
20. M. Uyanik, and K. Ishihara Chem. Commun. 2009 2086 2099
21. T. Dohi, A. Maruyama, M. Yoshimura, K. Morimoto, H. Tohma, and Y. Kita Angew. Chem., Int. Ed. 44 2005 6193 6196
22. M. Ochiai, Y. Takeuchi, T. Katayama, T. Sueda, and K. Miyamoto J. Am. Chem. Soc. 127 2005 12244 12245
23. Y. Yamamoto, and H. Togo Synlett 2006 798 800
24. T. Dohi, A. Maruyama, Y. Minamitsuji, N. Takenaga, and Y. Kita Chem. Commun. 2007 1224 1226
25. R.D. Richardson, T.K. Page, S. Altermann, S.M. Paradine, A.N. French, and T. Wirth Synlett 2007 538 542
26. J. Akiike, Y. Yamamoto, and H. Togo Synlett 2007 2168 2172
27. Y. Yamamoto, Y. Kawano, P.H. Toy, and H. Togo Tetrahedron 63 2007 4680 4687
28. R.D. Richardson, M. Desaize, and T. Wirth Chem. - Eur. J. 13 2007 6745 6754
29. A. Moroda, and H. Togo Synthesis 2008 1257 1261
30. S.M. Altermann, R.D. Richardson, T.K. Page, R.K. Schmidt, E. Holland, U. Mohammed, S.M. Paradine, A.N. French, C. Richter, A.M. Bahar, B. Witulski, and T. Wirth Eur. J. Org. Chem. 2008 5315 5328
31. Y. Kawano, and H. Togo Synlett 2008 217 220
32. Y. Kawano, and H. Togo Tetrahedron 65 2009 6251 6256
33. Y. Ishiwata, and H. Togo Tetrahedron Lett. 50 2009 5354 5357
34. M. Uyanik, T. Yasui, and K. Ishihara Bioorg. Med. Chem. Lett. 19 2009 3848 3851
35. A.P. Thottumkara, M.S. Bowsher, and T.K. Vinod Org. Lett. 7 2005 2933 2936
36. A. Schulze, and A. Giannis Synthesis 2006 257 260
37. M. Uyanik, M. Akakura, and K. Ishihara J. Am. Chem. Soc. 131 2009 251 262
38. M. Uyanik, R. Fukatsu, and K. Ishihara Org. Lett. 11 2009 3470 3473
39. L.R. Ojha, S. Kudugunti, P.P. Maddukuri, A. Kommareddy, M.R. Gunna, P. Dokuparthi, H.B. Gottam, K.K. Botha, D.R. Parapati, and T.K. Vinod Synlett 2009 117 121
40. A. Tanaka, and H. Togo Synlett 2009 3360 3364
41. Y. Ishiwata, and H. Togo Tetrahedron 65 2009 10720 10724
42. T. Dohi, Y. Minamitsuji, A. Maruyama, S. Hirose, and Y. Kita Org. Lett. 10 2008 3559 3562
43. Y. Minamitsuji, D. Kato, H. Fujioka, T. Dohi, and Y. Kita Aust. J. Chem. 62 2009 648 652
44. T. Yakura Synlett 2007 765 768
45. T. Yakura, Y. Tian, Y. Yamauchi, M. Omoto, and T. Konishi Chem. Pharm. Bull. 57 2009 252 256
46. S. Patai, Z. Rappoport, The Chemistry of the Quinonoid Compounds Vol. 2 1988 John Wiley Chichester Parts 1 and 2
47. R.H. Thomson, Naturally Occurring Quinones IV Recent Advances 1997 Blackie Academic & Professional London
48. P.J. Dudfield B.M. Trost, I. Fleming, Comprehensive Organic Synthesis Vol. 7 1991 Elsevier Oxford 345 356
49. P.T. Gallagher Contemp. Org. Synth. 3 1996 433 446
50. S. Akai, and Y. Kita Org. Prep. Proced. Int. 30 1998 603 629
51. W.M. Owton J. Chem. Soc., Perkin Trans. 1 1999 2409 2420
52. Y. Tamura, T. Yakura, H. Tohma, K. Kikuchi, and Y. Kita Synthesis 1989 126 127
53. R. Barret, and M. Daudon Tetrahedron Lett. 31 1990 4871 4872
54. R. Barret, and M. Daudon Synth. Commun. 20 1990 2907 2912
55. S.B. Claudio, J.A. Valderrama, R. Tapia, F. Farina, and M.C. Paredes Synth. Commun. 22 1992 955 960
56. A. Pelter, and S.M.A. Elgendy J. Chem. Soc., Perkin Trans. 1 1993 1891 1896
57. M.C. Marcotullio, F. Epifano, and M. Curini Trends Org. Chem. 10 2003 21 34
58. R. Gandhari, P.P. Maddukuri, and T.K. Vinod J. Chem. Educ. 84 2007 852 854
59. M. Frigerio, M. Santagostino, and S. Sputore J. Org. Chem. 64 1999 4537 4538
60. M. Mülbaier, and A. Giannis Angew. Chem., Int. Ed. 40 2001 4393 4394
61. M. Mülbaier, and A. Giannis ARKIVOC vi 2003 228 236
62. U. Ladziata, J. Willging, and V.V. Zhdankin Org. Lett. 8 2006 167 170
63. A.Y. Koposov, D.N. Litvinov, V.V. Zhdankin, M.J. Ferguson, R. McDonald, and R.R. Tykwinski Eur. J. Org. Chem. 2006 4791 4795
64. R.R. Karimov, Z.-G.M. Kazhkenov, M.J. Modjewski, E.M. Peterson, and V.V. Zhdankin J. Org. Chem. 72 2007 8149 8151
65. Parts of this work have appeared in preliminary communications: T. Yakura, and M. Omoto Chem. Pharm. Bull. 57 2009 643 645
66. T. Yakura, Y. Yamauchi, Y. Tian, and M. Omoto Chem. Pharm. Bull. 56 2008 1632 1634
67. X. Wang, and J.A. Porco Jr. Angew. Chem., Int. Ed. 44 2005 3067 3071
68. A. Soriente, A.D. Rocca, G. Sodano, and A. Trincone Tetrahedron 53 1997 4693 4702
69. L. Alcaraz, G. Macdonald, J.P. Ragot, N. Lewis, and R.J.K. Taylor J. Org. Chem. 63 1998 3526 3527
70. A. Ata, R.G. Kerr, C.E. Moya, and R.S. Jacobs Tetrahedron 59 2003 4215 4222
71. G. Wells, J.M. Berry, T.D. Bradshaw, A.M. Burger, A. Seaton, B. Wang, A.D. Westwell, and M.F.G. Stevens J. Med. Chem. 46 2003 532 541
72. J.M. Berry, T.D. Bradshaw, I. Fichtner, R. Ren, C.H. Schwalbe, G. Wells, E.-H. Chew, M.F.G. Stevens, and A.D. Westwell J. Med. Chem. 48 2005 639 644
73. C.J. Lion, C.S. Matthews, G. Wells, T.D. Bradshaw, M.F.G. Stevens, and A.D. Westwell Bioorg. Med. Chem. Lett. 16 2006 5005 5008
74. D.R. Milić, M.J. Gaić, W. Muster, J.J. Csanádi, and B.A. olaja Tetrahedron 53 1997 14073 14084
75. D.R. Milić, A. Kapor, B. Markov, B. Ribar, M. Strümpel, Z. Juranić, M.J. Gaić, and B.A. olaja Molecules 4 1999 338 352
76. D. Magdziak, S.J. Meek, and T.R.R. Pettus Chem. Rev. 104 2004 1383 1429
77. T. Matsuura, K. Omura, and R. Nakashima Bull. Chem. Soc. Jpn. 38 1965 1358 1362
78. W. Adam, H. Kili, and C.R. Saha-Möller Synlett 2002 510 512
79. M.C. DeRosa, and R.J. Crutchley Coord. Chem. Rev. 233-234 2002 351 371
80. B.F. Sels, D.E. De Vos, and P.A. Jacobs Angew. Chem., Int. Ed. 44 2005 310 313
81. K. Zilbeyaz, E. Sahin, and H. Kilic Tetrahedron: Asymmetry 18 2007 791 796
82. M.C. Carreño, M. González-López, and A. Urbano Angew. Chem., Int. Ed. 45 2006 2737 2741
83. S. Barradas, M.C. Carreño, M. González-López, A. Latorre, and A. Urbano Org. Lett. 9 2007 5019 5022
84. A. Pelter, and S.M.A. Elgendy J. Chem. Soc., Perkin Trans. 1 1993 1891 1896
85. E.N. Pitsinos, V.I. Moutsos, and O. Vageli Tetrahedron Lett. 48 2007 1523 1526
86. A.-S. Lin, K. Nakagawa-Goto, F.-R. Chang, D. Yu, S.L. Morris-Natschke, C.-C. Wu, S.-L. Chen, Y.-C. Wu, and K.-H. Lee J. Med. Chem. 50 2007 3921 3927
87. N.T. Vo, R.D.M. Pace, F. O'Hara, and M.J. Gaunt J. Am. Chem. Soc. 130 2008 404 405
88. S. Ranganathan, D. Ranganathan, S. Singh, and D. Bhattacharyya J. Chem. Soc., Chem. Commun. 1987 1887 1888
89. D. Magdziak, A.A. Rodriguez, R.W. Van De Water, and T.R.R. Pettus Org. Lett. 4 2002 285 288
90. S. Quideau, L. Pouységu, D. Deffieux, A. Ozanne, J. Gagnepain, I. Fabre, and M. Oxoby ARKIVOC vi 2003 106 119
91. N. Lebrasseur, J. Gagnepain, A. Ozanne-Beaudenon, J.-M. Léger, and S. Quideau J. Org. Chem. 72 2007 6280 6283
92. A. Ozanne, L. Pouységu, D. Depernet, B. Franois, and S. Quideau Org. Lett. 5 2003 2903 2906
93. F.-X. Felpin Tetrahedron Lett. 48 2007 409 412
94. ® and sodium bicarbonate has been reported: M.C. Carreño, M. González-López, and A. Urbano Angew. Chem., Int. Ed. 45 2006 2737 2741
95. P. Jacob III, P.S. Callery, A.T. Shulgin, and N. Castagnoli Jr. J. Org. Chem. 41 1976 3627 3629
96. S. Nojima, C. Schal, F.X. Webster, R.G. Santangelo, and W.L. Roelofs Science 307 2005 1104 1106
97. K.C. Nicolaou, H. Li, A.L. Nold, D. Pappo, and A. Lenzen J. Am. Chem. Soc. 129 2007 10356 10357
98. L.F. Tietze, R.R. Singidi, and K.M. Gericke Chem. - Eur. J. 13 2007 9939 9947
99. H. Tohma, H. Morioka, Y. Harayama, M. Hashizume, and Y. Kita Tetrahedron Lett. 42 2001 6899 6902
100. B.E. Love, J. Bonner-Stewart, and L.A. Forrest Synlett 2009 813 817
101. H. Irngartinger, and B. Stadler Eur. J. Org. Chem. 1998 605 626
102. 24b
103. F. Alonso, and M. Yus Tetrahedron 48 1992 2709 2714
104. C.D. Gutsche, and K.H. No J. Org. Chem. 47 1982 2708 2712
105. W.N. White, D. Gwynn, R. Schlitt, C. Girard, and W. Fife J. Am. Chem. Soc. 80 1958 3271 3277
106. A.K. Sinhababu, M. Kawase, and R.T. Borchardt Synthesis 1988 710 712
107. E.C.L. Gauiter, N.J. Lewis, A. McKillop, and R.J.K. Taylor Synth. Commun. 24 1994 2989 3008
108. T. Saitoh, E. Suzuki, A. Takasugi, R. Obata, Y. Ishikawa, K. Umezawa, and S. Nishiyama Bioorg. Med. Chem. Lett. 19 2009 5383 5386
109. J.L. García Ruano, C. García Paredes, and C. Hamdouchi Tetrahedron: Asymmetry 10 1999 2935 2944
110. N.-H. Nam, Y.-J. You, Y. Kim, D.-H. Hong, H.-M. Kim, and B.Z. Ahn Bioorg. Med. Chem. Lett. 11 2001 51173 51176
111. J.C. Colbert, and M.L. Robert J. Am. Chem. Soc. 68 1946 270 271
112. M. Novak, M.J. Poturalski, W.L. Johnson, M.P. Jones, Y. Wang, and S.A. Glover J. Org. Chem. 71 2006 3778 3785