Nickel-catalyzed direct electrochemical cross-coupling between aryl halides and activated alkyl halides

Journal of Organic Chemistry

Volumn 61, Issue 5, 1996, Pages 1748-1755

  Durandetti, Muriel ^a   Nédélec, Jean Yves ^a   Périchon, Jacques ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001044296     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9518314     Document Type: Article

References (66)

1. Kharash, M. S.; Reinmuth, O. Grignard Reactions of Nonmetallic Substances; Coustable; London, 1954.
2. (a) Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5531.
3. (b) Bumagin, N. A.; Kasatkin, A.; Beletskaya, I. P. Bull Acad. Sci. USSR 1984, 33, 1696.
4. (a) Wenkert, E.; Fernandes, J. B.; Michelotti, E. L.; Swindell, C. S. Synthesis 1983, 701.
5. (b) Okamura, H.; Takei, H. Tetrahedron Lett. 1979, 20, 3425.
6. (a) Kosugi, M.; Sasazawa, K.; Shimizu, Y.; Migita, T. Chem. Lett. 1977, 301.
7. (b) Suzuki, S.; Shiono, M.; Fujita, Y. Synthesis 1983, 804.
8. (a) Matsushita, H.; Negishi, E. I. J. Am. Chem. Soc 1981, 103, 2882.
9. (b) Negishi, E. I.; Chatterjee, S.; Matsushita, H. Tetrahedron Lett. 1981, 22, 3737.
10. (c) Pelter, A.; Rowlands, M.; Clements, G. Synthesis 1987, 1, 51.
11. (d) Zhu, L.; Wehmeyer, R. M ; Rieke, R. D. J. Org. Chem. 1991, 56, 1445.
12. Amano, T.; Yoshikawa, K.; Sano, T.; Ohuchi, Y.; Shiono, M.; Ishiguro, M.; Fujita, Y. Synth. Commun. 1986, 16, 499.
13. Chaussard, J.; Folest, J. C.; Nédélec, J. Y.; Périchon, J.; Sibille, S.; Troupel, M. Synthesis 1990, 1, 369.
14. Conan, A.; Sibille, S.; d'Incan, E.; Périchon, J. J. Chem. Soc., Chem. Commun. 1990, 48.
15. Durandetti, M.; Sibille, S.; Nédélec, J.-Y.; Périchon, J. Synth. Commun. 1994, 2, 145
16. Rollin, Y.; Troupel, M.; Tuck, D.; Périchon J. J. Organomet. Chem. 1986, 303, 131.
17. Nicholson, R. S.; Shain, I. Anal. Chem. 1964, 36, 706.
18. Results to be published.
19. (a) Durandetti, S.; Sibille, S.; Périchon, J. J. Org. Chem. 1989, 54, 2198.
20. (b) Conan, A.; Sibille, S.; Périchon, J. J. Org. Chem. 1991, 56, 2018.
21. (c) Sibille, S.; Ratovelomanana, V.; Périchon, J. J. Chem. Soc., Chem. Commun. 1992, 283.
22. Folest, J. C.; Périchon, J.; Fauvarque, J. F.; Jutand, A. J. Organometal. Chem. 1988, 342, 259.
23. (a) Hegedus, L S.; Miller, L. L. J. Am. Chem. Soc. 1975, 97, 459.
24. (b) Kim, Y. J.; Sato, R.; Maruyama, T.; Osakada, T.; Yamamoto, T. J. Chem Soc., Dalton Trans. 1994, 943.
25. Bunnett, J. F. Acc. Chem. Res. 1978, 11, 413.
26. Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852.
27. (a) Dell'Erba, C.; Novi, M.; Petrillo, G.; Tavani, C. Tetrahedron 1992, 48, 325.
28. (b) Dell'Erba, C.; Novi, M.; Petrillo, G. Tavani, C. Tetrahedron 1994, 50, 3529.
29. D'Incan, E.; Sibille, S.; Périchon, J. Tetrahedron Lett. 1986, 27, 4175.
30. Binovic, K.; Vrancea, S. Chim. Ther. 1968, 5, 313.
31. Bakshi, S. P.; Turner, E. E. J. Chem Soc. 1961, 171.
32. (a) Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833.
33. (b) Fauvarque, J. F.; Jutand, A. J. Organomet. Chem. 1977, 132, C17.
34. (c) Fauvarque, J. F.; Jutand, A. J. Organomet. Chem., 1979, 177, 273.
35. (d) Yamanaka, H.; An-naka, M.; Kondo, Y.; Sakamoto, T. Chem. Pharm. Bull. 1985, 33, 4309.
36. (e) Klingstedt, T.; Frejd, T. Organometatlics 1983, 2, 598.
37. Rieu, J. P.; Boucherle, A.; Cousse, H. Mouzin, G Tetrahedron 1986, 42, 4095.
38. Sock, O.; Troupel, M.; Périchon, J. Tetrahedron Lett. 1985, 26, 1509.
39. Chausard, J.; Troupel, M.; Jacob, G.; Juhasz, J. P. J. Appl. Electrochem. 1989, 19, 345.
40. Uchino, M.; Asagi, K.; Yamamoto, A. Ikeda, S. J. Organamet. Chem. 1975, 84, 93.
41. Dunach, E.; Périchon, J. J. Organomet. Chem. 1988, 352, 239.
42. Venanzi, L. J. Chem. Soc. 1958, 719.
43. Van Hecke, G. R.; Horrocks, W. W. Inorg. Chem. 1966, 5, 1968.
44. Korte, D. E.; Hegedus, L. S. Wirth, R. K. J. Org. Chem. 1977, 42, 1329.
45. Lin, J.-Y.; Yoshida, S.; Takahashi, N. Agric. Biol. Chem. 1972, 36, 506.
46. Niwa, M.; Noda, H.; Kobayashi, H. Yamamura, S. Chem. Lett. 1980, 85.
47. Coutts, R. T.; Malicky, J. L. Can. J. Chem. 1973, 51, 1402.
48. Inaba, S.-I.; Rieke, R. D. J. Org. Chem. 1985, 50, 1373.
49. Benhaddou, R.; Czernecki, S.; Ville, G.; Zegar, A. Organometallics 1988, 7, 2435.
50. Gompper, R.; Vogt, H. H. Chem. Ber. 1981, 114, 2866.
51. Austin, E.; Ferravoli, C. G.; Alonso, R. A.; Rossi, R. A. Tetrahedron 1993, 49, 4495.
52. Tamaru, Y.; Yamada, Y.; Yoshida, Z.-I. J. Org. Chem. 1978, 43, 3396.
53. Tamuray, Shirouchi, Y. Haruta, J. Synthesis 1984, 231.
54. Miyamoto, K. Tsuchiya, S. Ohta, H. J. Fluorine Chem. 1992, 59, 225.
55. Biagi, G.; Livi, O. Verugi, E. Farmaco Ed. Sc. 1988, 43, 597.
56. Numao, N.; Hamada, T.; Yonemitsu, O. Tetrahedron 1978, 34, 1889.
57. Shono, T.; Kashinura, S.; Nogusa, H. J. Org. Chem. 1984, 49, 2043.
58. Ogura, K. Mitamura, S.; Kishi, G. Synthesis 1979, 880.
59. Pak, C. S.; Lee, E.; Lee, G. H. J. Org. Chem. 1993, 58, 1523.
60. Goument, B.; Duhamel, L.; Maugé, R Bull. Soc. Chim. Fr. 1993, 130, 459.
61. Martin, M. M.; Gleicher, G. J. J. Am. Chem. Soc. 1964, 86, 233.
62. Lajis, N. H.; Niyaz, Khan M. Tetrahedron 1992, 48, 1109.
63. Gascoyne, J. M.; Mitchell, P. J.; Phillips, L. J. Chem. Soc. Perkin Trans. 2 1977, 1051.
64. Reinecke, M. G.; Del Mazza, D. J. Org. Chem. 1989, 54, 2142.
65. Lee, C. W.; Alper, H. J. Org. Chem. 1995, 60, 250.
66. Barton, D. H. R.; Bohé, L.; Lusinchi, X. Tetrahedron 1990, 46, 5273.