Development of Novel Oxidation Reactions in Water Using Hypervalent Iodine Reagents

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 62, Issue 2, 2004, Pages 116-127

  Tohma, Hirofumi ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Environmentally benign reaction; Hypervalent iodine reagent; Oxidation; Polymer supported reagent; Water

Indexed keywords

ANODIC OXIDATION; ENVIRONMENTAL IMPACT; ORGANIC COMPOUNDS; SAFETY FACTOR; TOXICITY; WATER;

ACTIVATION METHODS; ENVIRONMENTALLY BENIGN REACTION; HYPERVALENT IODINE REAGENT; POLYMER-SUPPORTED REAGENT;

IODINE;

EID: 2142653615     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.62.116     Document Type: Article

References (83)

1. (a) P. J. Stang, V. V. Zhdankin Chem. Rev., 96, 1123 (1996);
2. (b) A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego, 1997;
3. (c) T. Kitamura, Y. Fujiwara, Org. Prep. Proced. Int., 29, 409 (1997);
4. (d) M. Ochiai, Chemistry in Hypervalent Compounds, K.-Y. Akiba, ed., Wiley-VCH, New York, 1999, Chap.12;
5. (e) T. Wirth, U. H. Hirt, Synthesis, 1999, 1271;
6. (f) V. V. Zhdankin, P. J. Stang, Chem. Rev., 102, 2523 (2002);
7. (g) Hypervalent Iodine Chemistry (Top. Curr. Chem. 224); T. Wirth, ed., Springer-Verlag, Berlin, Heidelberg, 2003
8. (a) Y. Tamura, T. Yakura, J. Haruta, Y. Kita, J. Org. Chem., 52, 3927 (1987);
9. (b) Y. Kita, H. Tohma, K. Kikuchi, M. Inagaki, T. Yakura, ibid., 56, 435 (1991);
10. (c) Y. Kita, H. Tohma, M. Inagaki, K. Hatanaka, T. Yakura, J. Am. Chem. Soc., 114, 2175 (1992);
11. (d) Y. Kita, H. Tohma, K. Hatanaka, T. Takada, S. Fujita, S. Mitoh, H. Sakurai, S. Oka, ibid., 116, 3684 (1994);
12. (e) Y. Kita, T. Takada, M. Gyoten, H. Tohma, M. H. Zenk, J. Eichhorn, J. Org. Chem., 61, 5857 (1996);
13. (f) Y. Kita, M. Arisawa, M. Gyoten, M. Nakajima, R. Hamada, H. Tohma, T. Takada, ibid., 63, 6625 (1998);
14. (g) Y. Kita, M. Egi, T. Takada, H. Tohma, Synthesis, 1999, 885;
15. (h) H. Tohma, H. Morioka, S. Takizawa, M. Arisawa, Y. Kita, Tetrahedron, 57, 345 (2001);
16. (i) H. Tohma, Y. Harayama, M. Hashizume, M. Iwata, Y. Kiyono, M. Egi, Y. Kita, J. Am. Chem. Soc., 125, 11235 (2003)
17. (a) C.-J. Li, Organic Reactions in Aqueous Media, John Wiley&Sons, Inc. 1997;
18. (b) P. A. Grieco, Organic Synthesis in Water, Blackie Academic&Professional, 1998;
19. (c) S. Kobayashi, ed., Adv. Synth. Catal., 344, Issue 3-4 (Special issue of aqueous reactions) (2002)
20. (a) R. Noyori, M. Aoki, K. Sato, Chem. Commun., 2003, 1977 and references cited therein;
21. (b) G.-J. Brink, I. W. C. E. Arends, R. A. Sheldon, Science, 287, 1636 (2000)
22. H. W. Richter, B. R. Cherry, T. D. Zook, G. F. Koser, J. Am. Chem. Soc., 119, 9614 (1997)
23. (a) R. M. Moriarty, R. K. Vaid, M. P. Duncan, M. Ochiai, M. Inenaga, Y. Nagao, Tetrahedron Lett., 29, 6913 (1988);
24. (b) M. Ochiai, M. Inenaga, Y. Nagao, R. M. Moriarty, R. K. Vaid, M. P. Duncan, ibid., 29, 6917 (1988);
25. (c) R. M. Moriarty, O. Prakash, M. P. Duncan, R. K. Vaid, N. Rani, J. Chem. Res. (S), 1996, 432
26. (a) R. A. Moss, K. W. Alwis, J. S. Shin, J. Am. Chem. Soc., 106, 2651 (1984);
27. (b) R. A. Moss, P. Scrimin, R. T. Rosen, Tetrahedron Lett., 28, 251 (1987)
28. (a) D. Barbas, S. Spyroudis, A. Varvoglis, J. Chem. Res. (S), 1985, 186;
29. (b) K. R. Roh, K. S. Kim, Y. H. Kim, Tetrahedron Lett., 32, 793 (1991)
30. H. Tohma, S. Takizawa, H. Watanabe, Y. Kita, Tetrahedron Lett., 39, 4547 (1998)
31. H. Tohma, T. Maegawa, Y. Kita, ARKIVOC vi, 62 (2003)
32. (a) H. B. Kagan, Catalytic Asymmetric Synthesis, I. Ojima, ed., VCH. New York, 1993, p 203;
33. (b) E. G. Mata, Phosphorus, Sulfur, and Silicon, 117, 231 (1996)
34. (a) A. W. Czarnik, J. Org. Chem., 49, 924 (1984);
35. (b) T. Imamoto, H. Koto, Chem. Lett., 1986, 967;
36. (c) D. G. Ray, III, G. F. Koser, J. Am. Chem. Soc., 112, 5672 (1990);
37. (d) M. Ochiai, Y. Takaoka, Y. Masaki, Y. Nagao, M. Shiro, ibid., 112, 5677 (1990);
38. (e) E. Hatzigrigoriou, A. Varvoglis, M. Bakola-Christianopoulou, J. Org. Chem., 55, 315 (1990);
39. (f) D. G. Ray, III, G. F. Koser, ibid., 57, 1607 (1992);
40. (g) M. Xia, Z.-C. Chen, Synth. Commun., 27, 1315 (1997);
41. (h) U. H. Hirt, B. Spingler, T. Wirth, J. Org. Chem., 63, 7674 (1998);
42. (i) V. V. Zhdankin, J. T. Smart, P. Zhao, P. Kiprof, Tetrahedron Lett., 41, 5299 (2000)
43. H. Tohma, S. Takizawa, H. Morioka, T. Maegawa, Y. Kita, Chem. Pharm. Bull., 48, 445 (2000)
44. H. Tohma, S. Takizawa, H. Watanabe, Y. Fukuoka, T. Maegawa, Y. Kita, J. Org. Chem., 64, 3519 (1999)
45. IBX, DMP: (a) D. B. Dess, J. C. Martin, J. Am. Chem. Soc., 113, 7277 (1991).: (a) J. B. Plumb, P. J. Harper, Chem. Eng. News (July 16), 3 (1990); (b) G. A. Cain, S. Bobkov, M. Czerwinski, Chem. Eng. News (July 1), 4 (2002)
46. IBX, DMP: (a) D. B. Dess, J. C. Martin, J. Am. Chem. Soc., 113, 7277 (1991).: (a) J. B. Plumb, P. J. Harper, Chem. Eng. News (July 16), 3 (1990); (b) G. A. Cain, S. Bobkov, M. Czerwinski, Chem. Eng. News (July 1), 4 (2002)
47. IBX, DMP: (a) D. B. Dess, J. C. Martin, J. Am. Chem. Soc., 113, 7277 (1991).: (a) J. B. Plumb, P. J. Harper, Chem. Eng. News (July 16), 3 (1990); (b) G. A. Cain, S. Bobkov, M. Czerwinski, Chem. Eng. News (July 1), 4 (2002)
48. (a) T. Takaya, H. Enyo, E. Imoto, Bull. Chem. Soc. Jpn., 41, 1032 (1968);
49. (b) R. S. Varma, R. Dahiya, R. K. Saini, Tetrahedron Lett., 38, 7029 (1997);
50. (c) T. Kawashima, K. Hoshiba, N. Kano, J. Am. Chem. Soc., 123, 1507 (2001)
51. (a) T. Yokoo, K. Matsumoto, K. Oshima, K. Utimoto, Chem. Lett., 1993, 571;
52. (b) P. Müllar, J. Godoy, Tetrahedron Lett., 22, 2361 (1981);
53. (c) W. Adam, F. G. Gelalcha, C. R. Saha-Möller, V. R. Stegmann, J. Org. Chem., 65, 1915 (2000);
54. (d) W. Adam, S. Hajra, M. Herderich, C. R. Saha-Möller, Org. Lett., 2, 2773 (2000)
55. (a) A. De Mico, R. Margarita, L. Parlanti, A. Vescovi, G. Piancatelli, J. Org. Chem., 62, 6974 (1997);
56. (b) K. Sakuratani, H. Togo, Synthesis, 2003, 21
57. H. Tohma, S. Takizawa, T. Maegawa, Y. Kita, Angew. Chem., Int. Ed., 39, 1306 (2000)
58. (a) E. J. Corey, A. Palani, Tetrahedron Lett., 36, 3485 (1995);
59. (b) J. Roels, P. Metz, Synlett, 2001, 789
60. H. Tohma, T. Maegawa, S. Takizawa, Y. Kita, Adv. Synth. Catal., 344, 328 (2002)
61. (a) R. Kaneko, K. Seki, M. Suzuki, Chem. Ind., 1971, 1016;
62. (b) E. J. Corey, B. Samuelsson, J. Org. Chem., 49, 4735 (1984);
63. (c) A. W. Guest, Tetrahedron Lett., 27, 3049 (1986);
64. (d) J. N. Milovanovic, M. Vasojevic, S. Gojkovic, J. Chem. Soc., Perkin Trans. 2, 1991, 1231;
65. (e) A. B. Smith, III, G. A. Sulikowski, M. M. Sulikowski, K. Fujimoto, J. Am. Chem. Soc., 114, 2567 (1992);
66. (f) C. E. McDonald, L. E. Nice, A. W. Shaw, N. B. Nestor, Tetrahedron Lett., 34, 2741 (1993);
67. (g) J. S. Foot, H. Kanno, G. M. P. Giblin, R. J. K. Taylor, Synlett, 2002, 1293
68. H. Tohma, T. Maegawa, Y. Kita, Synlett, 2003, 723
69. H. J. Lucus, E. R. Kennedy, Org. Synth., Coll., 3, 485 (1955)
70. S. Sakamoto, M. Pujita, K. Kim, K. Yamaguchi, Tetrahedron, 56, 955 (2000)
71. P. A. Evans, T. A. Brandt, J. Org. Chem., 62, 5321 (1997)
72. (a) A. Kirschning, H. Monenschein, C. Schmeck, Angew. Chem., Int. Ed. 38, 2594 (1999);
73. (b) H. Monenschein, G. Sourkouni-Argirusi, K. M. Schubothe, T. O'Hare, A. Kirschning, Org. Lett., 1, 2101 (1999)
74. Y. Tamura, T. Yakura, H. Tohma, K. Kikuchi, Y. Kita, Synthesis, 1989, 126
75. (a) T.-L. Ho, Synthesis, 1973, 347;
76. (b) P. Jacob, III, P. S. Callery, A. T. Shulgin, N. Castagnoli, Jr., J. Org. Chem., 41, 3627 (1976);
77. (c) F. M. Hauser, S. Prasanna, J. Am: Chem. Soc., 103, 6378 (1981)
78. C. D. Snyder, H. Rapoport, J. Am. Chem. Soc., 94, 227 (1972)
79. H. Tohma, H. Morioka, Y. Harayama, M. Hashizume, Y. Kita, Tetrahedron Lett., 42, 6899 (2001)
80. M. Okawara, K. Mizuta, Kogyo Kagaku Zasshi, 64, 232 (1961).
81. H. Togo, K. Sakuratani, Synlett, 2002, 1966
82. W. Sun, H. Wang, C. Xia, J. Li, P. Zhao, Angew. Chem., Int. Ed., 42, 1042 (2003)