Recyclable polymer-supported iodobenzene-mediated electrocatalytic fluorination in ionic liquid

Advanced Synthesis and Catalysis

Volumn 352, Issue 16, 2010, Pages 2757-2760

  Sawamura, Takahiro ^a   Kuribayashi, Shunsuke ^a   Inagi, Shinsuke ^a   Fuchigami, Toshio ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

electrochemical fluorination; green chemistry; hypervalent iodoarenes; ionic liquids; mediators

Indexed keywords

EID: 78349280013     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000501     Document Type: Article

References (69)

1. V. A. Soloshonok, Enantiocontrolled Synthesis of Fluoro-Organic Compounds, Stereochemical Challenges and Biomedicinal Targets, Wiley, New York, 1999
2. J.-P. Begue, D. B.-Delpon, Bioorganic and Medicinal Chemistry of Fluorine, John Wiley & Sons, New Jersey, 2008.
3. T. Fuchigami, in: Organic Electrochemistry, 4 th edn., (Eds.:, H. Lund, O. Hammerich,), Dekker, New York, 2001, p 1035
4. T. Fuchigami, T. Tajima, in: Fluorine-Containing Synthons, (Ed.:, V. Soloshonok,), Chapter 15, ACS Symposium Series 911, ACS, Washington, DC, 2005
5. T. Fuchigami, T. Tajima, in: Current Fluoroorganic Chemistry. New Synthetic Directions, Technologies, Materials, and Biological Applications, (Ed.:, V. Soloshonok,), Chapter 5, ACS Symposium Series 949, ACS, Washington, DC, 2007.
6. M. Hasegawa, H. Ishii, Y. Cao, T. Fuchigami, J. Electrochem. Soc. 2006, 153, D 162 -D 166
7. M. Hasegawa, T. Fuchigami, Green Chem. 2003, 5, 512 - 515
8. S. Inagi, T. Sawamura, T. Fuchigami, Electrochem. Commun. 2008, 10, 1158 - 1160
9. T. Sawamura, S. Inagi, T. Fuchigami, J. Electrochem. Soc. 2009, 156, E 26 -E 28
10. S. Inagi, S. Hayashi, T. Fuchigami, Chem. Commun. 2009, 1718 - 1720
11. S. Hayashi, S. Inagi, T. Fuchigami, Macromolecules 2009, 42, 3755 - 3760.
12. V. Childs, L. Christensen, F. W. Klink, C. F. Kolpin, in: Organic Electrochemistry, 3 rd edn., (Eds.:, H. Lund, M. M. Baizer,), Marcel Dekker, New York, Chapter 26, 1991
13. M. R. Shaaban, H. Ishii, T. Fuchigami, J. Org. Chem. 2000, 65, 8685 - 8689.
14. T. Fuchigami, M. Sano, J. Electroanal. Chem. 1996, 414, 81 - 84
15. T. Fuchigami, K. Mitomo, H. Ishii, A. Konno, J. Electroanal. Chem. 2001, 507, 30 - 33
16. T. Fuchigami, M. Tetsu, T. Tajima, H. Ishii, Synlett 2001, 1269 - 1271.
17. R. M. Moriarty, R. K. Vaid, Synthesis 1990, 431 - 447
18. P. J. Stang, Angew. Chem. 1992, 104, 281 - 292
19. Angew. Chem. Int. Ed. Engl. 1992, 31, 274 - 285
20. O. Prakash, N. Saini, P. K. Sharma, Synlett 1994, 221 - 227
21. T. Kitamura, Yuki Gosei Kagaku Kyokaishi 1995, 53, 893 - 905
22. P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123 - 1178
23. T. Umemoto, Chem. Rev. 1996, 96, 1757 - 1778
24. A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego, CA, 1997
25. H. Togo, Y. Hoshina, G. Nogami, M. Yokoyama, Yuki Gosei Kagaku Kyokaishi 1997, 55, 90 - 98
26. A. Varvoglis, Tetrahedron 1997, 53, 1179 - 1255
27. V. V. Zhdankin, Rev. Heteroat. Chem. 1997, 17, 133 - 151
28. T. Muraki, H. Togo, M. Yokoyama, Rev. Heteroat. Chem. 1997, 17, 213 - 243
29. A. Varvoglis, S. Spyroudis, Synlett 1998, 221 - 232
30. V. V. Zhdankin, P. J. Stang, Tetrahedron 1998, 54, 10927 - 10966
31. R. M. Moriarty, O. Prakash, Adv. Heterocycl. Chem. 1998, 69, 1 - 87
32. V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523 - 2584
33. T. Wirth, Hypervalent iodine Chemistry: Modern Developments in Organic Synthesis, Topics in Current Chemistry, Springer Verlag, Berlin, Heidelberg, 2003
34. V. V. Zhdankin, P. J. Stang, Chem. Rev. 2008, 108, 5299 - 5358.
35. Y. Kita, T. Takada, H. Tohma, Pure Appl. Chem. 1996, 68, 627 - 630
36. T. Wirth, Angew. Chem. 2001, 113, 2893 - 2895
37. Angew. Chem. Int. Ed. 2001, 40, 2812 - 2814
38. H. Togo, M. Katohgi, Synlett 2001, 565 - 581
39. T. Wirth, Angew. Chem. 2005, 117, 3722 - 3731
40. Angew. Chem. Int. Ed. 2005, 44, 3656 - 3665
41. R. D. Richardson, T. Wirth, Angew. Chem. 2006, 118, 4510 - 4512
42. Angew. Chem. Int. Ed. 2006, 45, 4402 - 4404.
43. M. Zupan, A. Pollak, J. Chem. Soc. Chem. Commun. 1975, 715
44. A. Gergorcic, M. Zupan, Bull. Chem. Soc. Jpn. 1977, 50, 517 - 520
45. A. Gergorcic, M. Zupan, J. Chem. Soc. Perkin Trans. 1 1977, 1446 - 1459
46. B. Sket, M. Zupan, P. Zupet, Tetrahedron 1984, 40, 1603 - 1606
47. T. B. Patrick, J. J. Scheihel, W. E. Hall, Y. H. Lee, J. Org. Chem. 1980, 45, 4492 - 4494
48. J. J. Edmunds, W. B. Motherwell, J. Chem. Soc. Chem. Commun. 1989, 881 - 882
49. W. B. Motherwell, J. A. Wilkinson, Synlett 1991, 191 - 192
50. W. B. Motherwell, M. F. Greaney, J. J. Edmunds, J. W. Steed, J. Chem. Soc. Perkin Trans. 1 2002, 2816 - 2826
51. N. Yoneda, J. Fluorine Chem. 2004, 125, 7 - 17.
52. T. Fuchigami, T. Fujita, J. Org. Chem. 1994, 59, 7190 - 7192
53. S. Hara, T. Hatakeyama, S.-Q. Chen, K. Ishi-i, M. Yoshida, M. Sawaguchi, T. Fukuhara, N. Yoneda, J. Fluorine Chem. 1998, 87, 189 - 192
54. T. Fujita, T. Fuchigami, Tetrahedron Lett. 1996, 37, 4725 - 4728.
55. T. Sawamura, S. Kuribayashi, S. Inagi, T. Fuchigami, Org. Lett. 2010, 12, 644 - 646.
56. M. Zupan, A. Pollak, J. Chem. Soc. Chem. Commun. 1975, 17, 715 - 716
57. M. Zupan, Collect. Czech. Chem. Commun. 1977, 42, 266 - 274.
58. H. Togo, G. Nogami, M. Yokoyama, Synlett 1998, 534 - 536
59. H. Togo, S. Abe, G. Nogami, M. Yokoyama, Bull. Chem. Soc. Jpn. 1999, 72, 2351 - 2356.
60. M. Schlosser, Tetrahedron 1978, 34, 3 - 17
61. W. S. Sheppard, C. M. Sharts, Organic. Fluorine Chemistry, W. A. Benjamin, New York, 1969
62. M. Hudlicky, Organic Fluorine Chemistry, Plenum, New York, 1971
63. R. D. Chambers, Fluorine in Organic Chemistry, Wiley, New York, 1973
64. C. M. Sharts, W. A. Sheppard, Org. React. (N.Y.), 1974, 21, 125 - 406
65. G. A. Boswell, W. C. Ripka, R. M. Scribner, C. W. Tullock, Org. React. (N.Y.), 1974, 21, 1- 124.
66. D. H. R. Barton, S. W. McCombie, J. Chem. Soc. Perkin Trans. 1 1975, 1574 - 1585.
67. S. Caddick, W. B. Motherwell, J. A. Wilkinson, J. Chem. Soc. Chem. Commun. 1989, 1348;.
68. H. Ishii, N. Yamada, T. Fuchigami, Chem. Commun. 2000, 1617 - 1618.
69. M. Hasegawa, T. Fuchigami, Electrochim. Acta 2004, 49, 3367 - 3372.