Study on Radical Amidation onto Aromatic Rings with (Diacyloxyiodo)arenes

Journal of Organic Chemistry

Volumn 63, Issue 15, 1998, Pages 5193-5200

  Togo, Hideo ^a   Hoshina, Yoichiro ^a   Muraki, Takahito ^a   Nakayama, Hiromasa ^a   Yokoyama, Masataka ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001299071     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980450y     Document Type: Article

References (76)

1. (a) Varvoglis, A. Synthesis 1984, 709.
2. (b) Umemoto, T. Yuki Gosei Kagaku Kyokaishi 1983, 41, 251.
3. (c) Ochiai, M.; Nagao, Y. Yuki Gosei Kagaku Kyokaishi 1986, 44, 660.
4. (d) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431.
5. (e) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365.
6. (f) Kitamura, T. Yuki Gosei Kagaku Kyokaishi 1995, 53, 893.
7. (g) Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221.
8. (h) Kita, Y.; Takada, T.; Tohma, H. Pure Appl. Chem. 1996, 68, 627
9. Muraki, T.; Togo, H.; Yokoyama, M. Rev. Heteroatom Chem. 1997, 17, 213.
10. (j) Zhdankin, V. V. Rev. Heteroatom Chem. 1997, 17, 133.
11. (a) Togo, H.; Aoki, M.; Yokoyama, M. Tetrahedron Lett. 1991, 32, 6559.
12. (b) Togo, H.; Aoki, M.; Yokoyama, M. Chem. Lett. 1991, 1691.
13. (c) Togo, H.; Aoki, M.; Yokoyama, M. Tetrahedron 1993, 49, 8241.
14. (d) Togo, H.; Aoki, M.; Kuramochi, T.; Yokoyama, M. J. Chem. Soc., Perkin Trans. 1 1993, 2417.
15. (e) Togo, H.; Aoki, M.; Yokoyama, M. Chem. Lett. 1992, 2169.
16. (f) Togo, H.; Taguchi, R.; Yamaguchi, K.; Yokoyama, M. J. Chem. Soc., Perkin Trans. 1 1995, 2135.
17. (g) Togo, H.; Muraki, T.; Yokoyama, M. Synthesis 1995, 155.
18. (h) Minisci, F.; Vismara, E.; Fontana, F.; Barbosa, M. C. N. Tetrahedron Lett. 1989, 30, 4569.
19. (i) Singh, R.; Just, G. Synth. Commun. 1988, 18, 1327.
20. (j) Concepción, J. I.; Francisco, C. G.; Freire, R.; Hernández, R.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1986, 51, 402.
21. (a) Concepción, J. I.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1984, 25, 1953.
22. (b) Francisco, C. G.; Freire, R.; Rodriguez, M. S.; Suárez, E. Tetrahedron Lett. 1987, 28, 3397.
23. (c) Freire, R.; Hernández, R.; Rodriguez, M. S.; Suárez, E. Tetrahedron Lett. 1987, 28, 981.
24. (d) Furuta, K.; Nagata, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 2215.
25. (e) Brimble, M. A.; Williams, G. M.; Baker, R.; James, M. Tetrahedron Lett. 1990, 31, 3043.
26. (f) de Armas, P.; Francisco, C. G.; Suárez, E. Angew. Chem., Int. Ed. Engl. 1992, 31, 1, 772.
27. (g) de Armas, P.; Francisco, C. G.; Suárez, E. J. Am. Chem. Soc. 1993, 115, 8865.
28. (h) Boto, A.; Betancor C.; Suárez, E. Tetrahedron Lett. 1994, 35, 5509.
29. (i) Boto, A.; Betancor C.; Suárez, E. Tetrahedron Lett. 1994, 35, 6993.
30. (j) Arencibia, T.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1994, 35, 7463.
31. (k) de Armas, P.; Francisco, C. G.; Suárez, E. Tetrahedron Lett. 1993, 34, 7731.
32. (l) Francisco, C. G.; González, C. C.; Suárez, E. Tetrahedron Lett. 1996, 37, 1687.
33. (m) Ellwood, C. W.; Pattenden, G. Tetrahedron Lett. 1991, 32, 1591.
34. (n) de Armas, P.; Concepción, J. I.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. J. Chem. Soc., Perkin Trans. 1 1989, 405.
35. (o) Hernández, R.; Marrero, J. J.; Suárez, E. Tetrahedron Lett. 1988, 29, 5982.
36. (a) de Armas, P.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. J. Chem. Soc., Perkin Trans. 1 1988, 3255.
37. (b) Dorta, R. L.; Francisco, C. G.; Suárez, E. J. Chem. Soc., Chem. Commun. 1989, 1168.
38. (c) de Armas, P.; Carrau, R.; Concepción, J. I.; Francisco, C. G.; Hernández, R.; Suárez, E. Tetrahedron Lett. 1985, 26, 2493.
39. (d) Hernández, R.; Medina, M. C.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1987, 28, 2533.
40. (e) Carrau, R.; Hernández, R.; Suárez, E. J. Chem. Soc., Perkin Trans, 1 1987, 943.
41. (a) Togo, H.; Muraki, T.; Yokoyama, M. Tetrahedron Lett. 1995, 36, 7089.
42. (b) Muraki, T.; Togo, H.; Yokoyama, M. Tetrahedron Lett. 1996, 37, 2441.
43. (c) Togo, H.; Muraki, T.; Hoshina, Y.; Yamaguchi, K.; Yokoyama, M. J. Chem. Soc., Perkin Trans, 1 1997, 787.
44. Preliminary report: Togo, H.; Hoshina, Y.; Yokoyama, M. Tetrahedron Lett. 1996, 37, 6129.
45. (a) Magnus, P.; Parry, D.; Iliadis, T.; Eisenbeis, S. A.; Fairhurst, R. A. J. Chem. Soc., Chem. Commun. 1994, 1543.
46. (b) Morimoto, Y.; Matsuda, F. Shirahama, H. Synlett 1991, 202.
47. (c) Staub, G. M.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. J. Am. Chem. Soc. 1992, 114, 1015.
48. (d) Neville, C. F.; Grundon, M. F.; Ramachandran, V. N.; Reisch, J. J. Chem. Soc., Perkin Trans. 1 1991, 259.
49. (e) Gellerman, G.; Babad, M.; Kashman, Y. Tetrahedron Lett. 1993, 34, 1827.
50. (f) Toyota, M.; Asoh, T.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401.
51. (a) Omura, S.; Nakagawa, A.; Hashimoto, H.; Oiwa, R.; Iwai, Y.; Hirano, A.; Shibukawa, N.; Kojima, Y. J. Antibiot. 1980, 33, 1395.
52. (b) Nakagawa, A.; Iwai, Y.; Hashimoto, H.; Miyazaki, N.; Oiwa, R.; Takahashi, Y.; Hirano, A.; Shibukawa, N.; Kojima, Y.; Omura, S. J. Antibiot. 1981, 34, 1408.
53. (a) Atwal, M. S.; Bauer, L.; Dixit, S. N.; Gearien J. E.; Megahy, M.; Morris, R.; Pokorny, C. J. Med. Chem. 1969, 12, 994.
54. (b) Daruwala, A. B.; Gearien, J. E.; Dunn, W. J., III; Benoit, P. S.; Bauer, L. J. Med. Chem. 1974, 17, 819
55. Comprehensive Heterocyclic Chemistry; Katrizky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, 1984.
56. (a) Neumann, W. P. Synthesis 1987, 665.
57. (b) Curran D. P. Synthesis 1988, 417 and 489.
58. (c) Smadja, W. Synlett 1994, 1.
59. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Baldwin, J. E., Ed.; Pergamon Press: Oxford, 1986.
60. Amination onto aromatic ring via ammyl radical: (a) Minisci, F.; Galli, R. Tetrahedron Lett. 1966, 2531. (b) Glover, S. A.; Goosen, A.; Laue, H. A. H. J. Chem. Soc., Perkin Trans. 1 1973, 1647. Amination onto aromatic ring via iminyl radical: (c) Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677. (d) Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1975, 291. Hofmann-Löffler-Freytag reaction: (e) Corey, E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82 1657. (f) Hertler, W. R.; Corey, E. J. J. Org. Chem. 1959, 24, 572. (g) Buchschacher, P.; Kalvoda, J.; Arigoni, D.; Jeger, O. J. Am. Chem. Soc. 1958, 80, 2905.
61. Amination onto aromatic ring via ammyl radical: (a) Minisci, F.; Galli, R. Tetrahedron Lett. 1966, 2531. (b) Glover, S. A.; Goosen, A.; Laue, H. A. H. J. Chem. Soc., Perkin Trans. 1 1973, 1647. Amination onto aromatic ring via iminyl radical: (c) Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677. (d) Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1975, 291. Hofmann-Löffler-Freytag reaction: (e) Corey, E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82 1657. (f) Hertler, W. R.; Corey, E. J. J. Org. Chem. 1959, 24, 572. (g) Buchschacher, P.; Kalvoda, J.; Arigoni, D.; Jeger, O. J. Am. Chem. Soc. 1958, 80, 2905.
62. Amination onto aromatic ring via ammyl radical: (a) Minisci, F.; Galli, R. Tetrahedron Lett. 1966, 2531. (b) Glover, S. A.; Goosen, A.; Laue, H. A. H. J. Chem. Soc., Perkin Trans. 1 1973, 1647. Amination onto aromatic ring via iminyl radical: (c) Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677. (d) Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1975, 291. Hofmann-Löffler-Freytag reaction: (e) Corey, E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82 1657. (f) Hertler, W. R.; Corey, E. J. J. Org. Chem. 1959, 24, 572. (g) Buchschacher, P.; Kalvoda, J.; Arigoni, D.; Jeger, O. J. Am. Chem. Soc. 1958, 80, 2905.
63. Amination onto aromatic ring via ammyl radical: (a) Minisci, F.; Galli, R. Tetrahedron Lett. 1966, 2531. (b) Glover, S. A.; Goosen, A.; Laue, H. A. H. J. Chem. Soc., Perkin Trans. 1 1973, 1647. Amination onto aromatic ring via iminyl radical: (c) Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677. (d) Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1975, 291. Hofmann-Löffler-Freytag reaction: (e) Corey, E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82 1657. (f) Hertler, W. R.; Corey, E. J. J. Org. Chem. 1959, 24, 572. (g) Buchschacher, P.; Kalvoda, J.; Arigoni, D.; Jeger, O. J. Am. Chem. Soc. 1958, 80, 2905.
64. Amination onto aromatic ring via ammyl radical: (a) Minisci, F.; Galli, R. Tetrahedron Lett. 1966, 2531. (b) Glover, S. A.; Goosen, A.; Laue, H. A. H. J. Chem. Soc., Perkin Trans. 1 1973, 1647. Amination onto aromatic ring via iminyl radical: (c) Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677. (d) Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1975, 291. Hofmann-Löffler-Freytag reaction: (e) Corey, E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82 1657. (f) Hertler, W. R.; Corey, E. J. J. Org. Chem. 1959, 24, 572. (g) Buchschacher, P.; Kalvoda, J.; Arigoni, D.; Jeger, O. J. Am. Chem. Soc. 1958, 80, 2905.
65. Amination onto aromatic ring via ammyl radical: (a) Minisci, F.; Galli, R. Tetrahedron Lett. 1966, 2531. (b) Glover, S. A.; Goosen, A.; Laue, H. A. H. J. Chem. Soc., Perkin Trans. 1 1973, 1647. Amination onto aromatic ring via iminyl radical: (c) Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677. (d) Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1975, 291. Hofmann-Löffler-Freytag reaction: (e) Corey, E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82 1657. (f) Hertler, W. R.; Corey, E. J. J. Org. Chem. 1959, 24, 572. (g) Buchschacher, P.; Kalvoda, J.; Arigoni, D.; Jeger, O. J. Am. Chem. Soc. 1958, 80, 2905.
66. Amination onto aromatic ring via ammyl radical: (a) Minisci, F.; Galli, R. Tetrahedron Lett. 1966, 2531. (b) Glover, S. A.; Goosen, A.; Laue, H. A. H. J. Chem. Soc., Perkin Trans. 1 1973, 1647. Amination onto aromatic ring via iminyl radical: (c) Forrester, A. R.; Gill, M.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1976, 677. (d) Forrester, A. R.; Gill, M.; Sadd, J. S.; Thomson, R. H. J. Chem. Soc., Chem. Commun. 1975, 291. Hofmann-Löffler-Freytag reaction: (e) Corey, E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82 1657. (f) Hertler, W. R.; Corey, E. J. J. Org. Chem. 1959, 24, 572. (g) Buchschacher, P.; Kalvoda, J.; Arigoni, D.; Jeger, O. J. Am. Chem. Soc. 1958, 80, 2905.
67. (a) Bordwell, F. G.; Ji, Guo-T.; Zhang, X. J. Org. Chem. 1991, 56, 5254.
68. (b) Bordwell, F. G.; Zhang, X.; Filler, R. J. Org. Chem. 1993, 58, 6067.
69. (c) Ratcliffe, A. J.; Warner, I. Tetrahedron Lett. 1995, 36, 3881.
70. Fukuyama, T.; Jow, C.-K.; Cheung, M. Tetrahedron Lett. 1995, 36, 6373.
71. (a) Neale, R. S. Synthesis 1971, 1.
72. (b) Wolff, M. E. Chem. Rev. 1963, 63, 55.
73. (a) Mckillop, A.; Kemp, D. Tetrahedron 1989, 45, 3299.
74. (b) Schmeisser, M.; Dahmen, K.; Sartori, P. Chem. Ber. 1967, 100, 1633.
75. (a) Mitsunobu, O.; Wada, M.; Sano, T. J. Am. Chem. Soc. 1972, 94, 679.
76. (b) Mitsunobu, O. Synthesis 1981, 1.