Highly Selective Electrochemical Fluorination of Organic Compounds

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 55, Issue 4, 1997, Pages 301-312

  Fuchigami, Toshio ^a   Konno, Akinori ^b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b SHIZUOKA UNIVERSITY   (Japan)

Author keywords

Electrochemical partial fluorination; Fluoroalkyl selenide; Fluoroalkyl sulfide; Hypervalent fluoroiodoarene; Indirect electrolysis; Mediator; Pulse electrolysis; Pummerer type reaction; Telluride; Triarylamine

Indexed keywords

AMINES; CHEMICAL REACTIONS; ELECTROCHEMISTRY; ELECTROLYSIS; ELECTROLYTES; FLUORINE COMPOUNDS;

ELECTROCHEMICAL PARTIAL FLUORINATION; FLUOROALKYL SELENIDE; FLUOROALKYL SULFIDE; FLUOROALKYL TELLURIDE; HYPERVALENT FLUOROIODOARENE; INDIRECT ELECTROLYSIS; MEDIATORS; PULSE ELECTROLYSIS; PUMMERER TYPE REACTION; TRIARYLAMINE;

ORGANIC COMPOUNDS;

EID: 0031121552     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.55.301     Document Type: Article

References (59)

1. T. Fuchigami, "Topics in Current Chemistry 170, Electrochemistry V", Springer-Verlag, Berlin, 1994, p.1;
2. "Selective Fluorination in Organic and Biological Chemistry", ed. by J.T. Welch, Am. Chem. Soc., Washington, D.C., 1991; N. Yoneda, Tetrahedron, 47, 5329 (1991);
3. "Selective Fluorination in Organic and Biological Chemistry", ed. by J.T. Welch, Am. Chem. Soc., Washington, D.C., 1991; N. Yoneda, Tetrahedron, 47, 5329 (1991);
4. W.V. Childs, L. Christensen, F.W. Klink, C. F. Kolpin, "Organic Electrochemistry, 3rd ed", eds. by H. Lund, M. M. Baizer, Marcel Dekker, New York, 1991, p.1103; I.N. Rozhkov, "Organic Electrochemistry, 2nd ed"., eds. by M.M. Baizer, H. Lund, Marcel Dekker, New York, 1983, p.805
5. W.V. Childs, L. Christensen, F.W. Klink, C. F. Kolpin, "Organic Electrochemistry, 3rd ed", eds. by H. Lund, M. M. Baizer, Marcel Dekker, New York, 1991, p.1103; I.N. Rozhkov, "Organic Electrochemistry, 2nd ed"., eds. by M.M. Baizer, H. Lund, Marcel Dekker, New York, 1983, p.805
6. I.N. Rozhkov, A.V. Bukhtiarov, N.D. Kuleshova, I.L. Knunyants, Izv. Akad. Nauk USSR 1207 (1970); Dokl. Chem. USSR (Engl. Transl.), 193, 618 (1970)
7. I.N. Rozhkov, A.V. Bukhtiarov, N.D. Kuleshova, I.L. Knunyants, Izv. Akad. Nauk USSR 1207 (1970); Dokl. Chem. USSR (Engl. Transl.), 193, 618 (1970)
8. E. Laurent, B. Marquet, R. Tardivel, H. Thiebault, Bull. Soc. Chim. Fr., 1986, 955; E. Laurent, B. Marquet, R. Tardivel, Tetrahedron, 45, 4431 (1989)
9. E. Laurent, B. Marquet, R. Tardivel, H. Thiebault, Bull. Soc. Chim. Fr., 1986, 955; E. Laurent, B. Marquet, R. Tardivel, Tetrahedron, 45, 4431 (1989)
10. T. Fuchigami, Rev. Heteroatom. Chem., 10, 155 (1994)
11. T. Fuchigami, Y. Nakagawa, T. Nonaka, Tetrahedron Lett., 27, 3869 (1986);
12. T. Fuchigami, Y. Nakagawa, K. Yamamoto, J. Org. Chem., 56, 137 (1991)
13. T. Fuchigami, K. Yamamoto, A. Konno, Tetrahedron, 47, 625 (1991)
14. T. Fuchigami, M. Shimojo, A. Konno, K. Nakagawa, J. Org. Chem. 55, 6074 (1990)
15. A. Konno, K. Nakagawa, T. Fuhcigami, J. Chem. Soc., Chem. Commun., 1991, 1027;
16. T. Fuchigami, A. Konno, K. Nakagawa, M. Shimojo, J. Org. Chem., 59, 937 (1994)
17. T. Fuchigami, S. Ichikawa, J. Org. Chem., 59, 607 (1994)
18. T. Fuchigami, H. Yano, A. Konno, J. Org. Chem., 56, 6731 (1991)
19. T. Umemoto, G. Tomizawa, Bull. Chem. Soc. Jp., 59, 3625 (1986)
20. T. Fuchigami, M. Shimojo, A. Konno, J. Org. Chem., 60, 3459 (1995)
21. T. Brigaud, E. Laurent, Tetrahedron Lett., 31, 2287 (1990)
22. Y. Takeuchi, N. Itoh, T. Koizumi, J. Am. Chem. Soc., 113, 6318 (1991)
23. A. Konno, T. Fuchigami, J. Appl. Electrochem., 25, 173 (1995)
24. S. Narizuka, A. Konno, H. Koshiyama, T. Fuchigami, J. Fluorine Chem., 73, 121 (1995)
25. T. Fuchigami, T. Hayashi, A. Konno, Tetrahedron Lett., 33, 3161 (1992)
26. K. Surowiec, T. Fuchigami, Tetrahedron Lett., 33, 1065 (1992)
27. T. Fuchigami, T. Fujita, A. Konno, Tetrahedron Lett., 35, 4153 (1994)
28. G.P. Gambaretto, M. Napoli, C. Franccaro, L. Conk, J. Fluorine Chem., 19, 427 (1982)
29. J.R. Ballinger, F.W. Teare, Electrochim. Acta, 30, 1075 (1985)
30. K. Makino, H. Yoshioka, J. Fluorine Chem., 39, 435 (1988)
31. J.H.H. Meurs, W. Eilenherg, Tetrahedron, 47, 705 (1991)
32. A. Konno, W. Naito, T. Fuchigami, Tetrahedron Lett., 33, 7017 (1992)
33. S. Narizuka, T. Fuchigami, J. Org. Chem., 58, 4200 (1993)
34. W.A. Slusarchyk, H.E. Applegate, P. Funke, W. Koster, M.S. Puar, M. Young, J.E. Dolfini, J. Org. Chem., 38, 943 (1973);
35. W.A. Spitzer, T. Goodson, M.O. Chaney, N.D. Jones, Tetrahedron Lett., 1974, 4311
36. T. Fuchigami, S. Narizuka, A. Konnos J. Org. Chem., 57, 3755 (1992)
37. S. Narizuka, A. Konno, H. Matsuyama, T. Fuchigami, DENKIKAGAKU, 61, 858 (1993)
38. S. Narizuka, T. Fuchigami, Bioorg. Med. Chem. Lett., 5, 1293 (1995)
39. K. Momota, M. Morita, Y. Matsuda, Electrochim Acta, 38, 1123 (1993)
40. T. Fuchigami, A. Konno, 211th Am. Chem. Soc. Meeting(New Orleans), No. FLUO-006 (1996)
41. A.W. Erian, A. Konno, T. Fuchigami, Tetrahedron Lett., 35, 7245 (1994);
42. idem., J. Org. Chem., 60, 7654 (1995)
43. A. Konno, T. Fuchigami, J. Org. Chem., to be submitted.
44. T. Yoshiyama, T. Fuchigami, Chem. Lett., 1992, 1995
45. T. Fuchigami, M. Sano, J. Electroanal. Chem., 414, 81 (1996)
46. M. Zupan, A. Pollak, J. Fluorine Chem., 7, 445 (1977)
47. T. Fuchigami, T. Fujita, J. Org. Chem., 59, 7190 (1994)
48. T. Fuchigami, T. Fujita, Tetrahedron Lett., 37, 4725 (1996)
49. K. Suda, K. Hotoda, M. Aoyagi, T. Takanami, J. Chem. Soc., Perkin Trans. 1, 1995, 1327
50. S. Hara, S.-Q. Chen, T. Hatakeyama, T. Fukuhara, M. Sekiguchi, N. Yoneda, Tetrahedron Lett., 36, 6511 (1995);
51. J. Yoshida, Y. Ishi Chi, S. Isoe, J. Am. Chem. Soc., 114, 7594 (1992);
52. M. Sono, N. Toyoda, Y. Shizuri, M. Tori, Tetrahedron Lett., 35, 9237 (1994);
53. P.Baroux, R. Tardivel, J. Shimonet, Tetrahedron Lett., 36, 3851 (1995);
54. K. Momota, H. Horio, K. Kato, M. Morita, Y. Matsuda, Etectrochim. Acta. 40, 233 (1995);
55. W. Dmowski, T. Kozlowski, ibid., 42, 513 (1997)