Direct and convenient synthesis of [bis(trifluoroacetoxy)iodo]arenes from iodoarenes

Bulletin of the Chemical Society of Japan

Volumn 79, Issue 1, 2006, Pages 142-144

  Hossain, Delwar ^a   Kitamura, Tsugio ^a  

^a SAGA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HIGH TEMPERATURE EFFECTS; POTASSIUM COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

IODOARENES;

OLEFINS;

[BIS(TRIFLUOROACETOXY)IODO]ARENE DERIVATIVE; BENZENE DERIVATIVE; IODOARENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; HIGH TEMPERATURE; SYNTHESIS;

EID: 33744941289     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.79.142     Document Type: Article

References (63)

1. Reviews on organohypervalent iodine compounds and their applications in organic synthesis: a) A. Varvoglis, Chem. Soc. Rev. 1981, 10, 377.
2. b) E. B. Merkushev, Russ. Chem. Rev. (Engl. Transl.) 1987, 56, 826.
3. c) M. Ochiai, Rev. Heteroat. Chem. 1989, 2, 92.
4. d) R. M. Moriarty, R. K. Vaid, G. F. Koser, Synlett 1990, 365.
5. e) R. M. Moriarty, R. K. Vaid, Synthesis 1990, 431.
6. f) A. Varvoglis, The Organic Chemistry of Polycoordinated Iodine, VCH, Weinheim, 1992.
7. g) P. J. Stang, Angew. Chem., Int. Ed. Engl. 1992, 31, 274.
8. h) O. Prakash, N. Sainai, P. K. Sharma, Synlett 1994, 221.
9. i) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123.
10. j) T. Umemoto, Chem. Rev. 1996, 96, 1757.
11. k) Y. Kita, T. Takada, H. Toma, Pure Appl. Chem. 1996, 68, 627.
12. l) A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego, 1997.
13. m) T. Kitamura, Y. Fujiwara, Org. Prep. Proced. Int. 1997, 29, 409.
14. n) A. Varvoglis, Tetrahedron 1997, 53, 1179.
15. o) T. Muraki, H. Togo, M. Yokoyama, Rev. Heteroat. Chem. 1997, 17, 213.
16. p) H. Togo, Y. Hoshina, G. Nogami, M. Yokoyama, Yuki Gosei Kagaku Kyokaishi 1997, 55, 90.
17. q) V. V. Zhdankin, Rev. Heteroat. Chem. 1997, 17, 133.
18. r) A. Kirschning, J. Prakt. Chem./Chem.-Ztg. 1998, 340, 184.
19. s) R. M. Moriarty, O. Prakash, Adv. Heterocycl. Chem. 1998, 69, 1.
20. t) A. Kirschning, Eur. J. Org. Chem. 1998, 2267.
21. u) V. V. Zhdankin, P. J. Stang, Tetrahedron 1998, 54, 10927.
22. v) A. Varvoglis, S. Spyroudis, Synlett 1998, 221.
23. w) Y. Kita, M. Egi, T. Takada, H. Thoma, Synthesis 1999, 885.
24. x) T. Wirth, V. H. Hirt, Synthesis 1999, 1271.
25. y) V. V. Grushin, Chem. Soc. Rev. 2000, 29, 315.
26. z) M. Ochiai, Y. Kitagawa, Yuki Gosei Kagaku Kyokaishi 2000, 58, 1048.
27. aa) G. Pohnert, J. Prakt. Chem. 2000, 342, 731.
28. bb) S. S. Chaudhari, Synlett 2000, 278.
29. cc) T. Wirth, Angew. Chem., Int. Ed. 2001, 40, 2812.
30. dd) H. Togo, M. Katohgi, Synlett 2001, 565.
31. ee) V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523.
32. ff) H. Togo, K. Sakuratani, Synlett 2002, 1966.
33. gg) Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis, ed. by T. Wirth, Springer-Verlag, Berlin, 2003.
34. hh) H. Thoma, Y. Kita, Adv. Synth. Catal. 2004, 346, 111.
35. ii) H. Thoma, Y. Kita, Yuki Gosei Kagaku Kyokaishi 2004, 62, 116.
36. jj) T. Wirth, Angew. Chem., Int. Ed. 2005, 44, 3656.
37. Applications of [bis(trifluoroacetoxy)iodo]arenes in organic synthesis: a) Y. Tamura, T. Yakura, H. Tohma, K. Kikuchi, Y. Kita, Synthesis 1989, 126.
38. b) Y. Kita, H. Tohma, K. Hatanaka, T. Takada, S. Fujita, S. Mitoh, H. Sakurai, S. Oka, J. Am. Chem. Soc. 1994, 116, 3684.
39. c) T. Takada, M. Arisawa, M. Gyoten, R. Hamada, H. Tohma, Y. Kita, J. Org. Chem. 1998, 63, 7698.
40. d) R. M. Moriarty, B. A. Berglund, R. Penmasta, Tetrahedron Lett. 1992, 33, 6065.
41. e) Y. Tamura, T. Yakura, Y. Shirouchi, J. Haruta, Chem. Pharm. Bull. 1986, 34, 1061.
42. f) G. Stork, K. Zhao, Tetrahedron Lett. 1989, 30, 287.
43. g) R. Benhida, P. Blanchard, J. L. Fourrey, Tetrahedron Lett. 1998, 39, 6849.
44. h) S. V. Ley, O. Schucht, A. W. Thomas, P. J. Murray, J. Chem. Soc., Perkin Trans. 1 1999, 1251.
45. i) Y. Kita, T. Yakura, H. Terashi, J. Haruta, Y. Tamura, Chem. Pharm. Bull. 1989, 37, 891.
46. j) K. Kanematsu, S. Morita, S. Fukushima, E. Osawa, J. Am. Chem. Soc. 1981, 103, 5211.
47. k) Y. Kita, H. Thoma, M. Inagaki, K. Hatanaka, Heterocycles 1992, 33, 503.
48. l) B. D. Gates, P. Dalidowicz, A. Tebben, A. Wang, J. S. Swenton, J. Org. Chem. 1992, 57, 2135.
49. m) G. M. Loudon, A. S. Radhakrishna, M. R. Almond, J. K. Blodgett, R. H. Boutin, J. Org. Chem. 1984, 49, 4272.
50. n) Y. Kikugawa, M. Kawase, Chem. Lett. 1990, 581.
51. o) Y. Kita, T. Takada, S. Mihara, H. Tohma, Synlett 1995, 211.
52. p) E. B. Merkushev, N. D. Simakhina, G. M. Koveshnikova, Synthesis 1980, 486.
53. q) S. Spyroudis, A. Varvoglis, J. Chem. Soc., Chem. Commun. 1979, 615.
54. r) O. V. Sing, Org. Prep. Proced. Int. 1993, 25, 693.
55. I. I. Maletina, V. V. Orda, L. M. Yagupolskii, J. Org. Chem. USSR (Engl. Transl.) 1974, 10, 294.
56. L. M. Yagupolskii, I. I. Maletina, N. V. Kondratenko, V. V. Orda, Synthesis 1977, 574.
57. T. M. Kasumov, V. K. Brel, Y. K. Grishin, N. S. Zefirov, P. J. Stang, Tetrahedron 1997, 53, 1145.
58. P. Kazmierczak, L. Skulski, Molecules 2002, 7, 810.
59. V. V. Zhdankin, M. C. Scheuller, P. J. Stang, Tetrahedron Lett. 1993, 34, 6853.
60. N. S. Zefirov, S. O. Safronov, A. A. Kaznacheev, V. V. Zhdankin, J. Org. Chem. USSR (Engl. Transl.) 1989, 25, 1807.
61. a) S. Spyroudis, A. Varvoglis, Synthesis 1975, 445.
62. b) J. D. White, G. Caravatti, T. B. Kline, E. Edstrom, K. C. Rice, A. Brossi, Tetrahedron 1983, 39, 2393.
63. N. W. Alcock, T. C. Waddington, J. Chem. Soc. 1963, 4103.