Fluorine-copper exchange reaction of α,β,γ,γ, γ-pentafluorocrotonates with organocuprates: Generation and cross-coupling reactions of β-metallated α,γ,γ,γ- tetrafluorocrotonates

Journal of Fluorine Chemistry

Volumn 149, Issue , 2013, Pages 95-103

  Yamada, Shigeyuki ^a   Takahashi, Toshio ^a   Konno, Tsutomu ^a   Ishihara, Takashi ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Addition elimination reaction; Fluorinated alkenes; Fluorine copper exchange; Organocuprates

Indexed keywords

EID: 84875439135     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2013.01.031     Document Type: Article

References (85)

1. H. Amii, and K. Uneyama Chem. Rev. 109 2009 2119 2183
2. For selective reports on the C-F bond cleavage of aryl fluorides using nickel catalyst, see: J.W. Dankwardt J. Organomet. Chem. 690 2005 932 938
3. N. Yoshikai, H. Mashima, and E. Nakamura J. Am. Chem. Soc. 127 2005 17978 17979
4. K. Lamm, M. Stollenz, M. Meier, H. Görls, and D. Walther J. Organomet. Chem. 681 2003 24 36
5. F. Mongin, L. Mojovic, B. Guillamet, F. Trécourt, and G. Quéguiner J. Org. Chem. 67 2002 8991 8994
6. T. Braun, R.N. Perutz, and M.I. Sladek Chem. Commun. 2001 2254 2255
7. V.P.W. Böhm, C.W.K. Gstöttmayr, T. Weskamp, and W.A. Herrmann Angew. Chem. Int. Ed. 40 2001 3387 3389
8. For selective reports on the C-F bond cleavage of aryl fluorides using palladium catalyst, see: Y.M. Kim, S. Yu, and J. Am Chem. Soc. 125 2003 1696 1697
9. R. Wilhelm, and D.A. Widdowson J. Chem. Soc., Perkin Trans. 1 2000 3808 3813
10. For a report on the C-F bond cleavage of aryl fluorides using copper catalyst, see: T.J. Korn, M.A. Schade, S. Wirth, and P. Knochel Org. Lett. 8 2006 725 728
11. For selective reports on the C-F bond cleavage of alkyl fluorides using transition metal catalyst, see: K. Fuchibe, T. Kaneko, K. Mori, and T. Akiyama Angew. Chem. Int. Ed. 48 2009 8070 8073
12. J. Terao, and N. Kambe Bull. Chem. Soc. Jpn. 79 2006 663 672
13. J. Terao, H. Watabe, and N. Kambe J. Am. Chem. Soc. 127 2005 3656 3657
14. J. Terao, S.A. Begum, A. Oda, and N. Kambe Synlett 2005 1783 1786
15. J. Terao, H. Todo, H. Watanabe, A. Ikumi, and N. Kambe Angew. Chem. Int. Ed. 43 2004 6180 6182
16. J. Terao, A. Ikumi, H. Kuniyasu, and N. Kambe J. Am. Chem. Soc. 125 2003 5646 5647
17. For C-F bond cleavage of alkenyl fluorides using low-valent zirconocenes, see: M. Fujiwara, J. Ichikawa, T. Okauchi, and T. Minami Tetrahedron Lett. 40 1999 7261 7265
18. G. Landelle, P.A. Champagne, X. Barbeau, and J.F. Paquin Org. Lett. 11 2009 681 684
19. F. Babudri, A. Cardone, L. De Cola, G.M. Farinola, G.S. Kottas, C. Martinelli, and F. Naso Synthesis 2008 1583 1588
20. J. Ichikawa, K. Sakoda, and Y. Wada Chem. Lett. 2002 282 283
21. V.A. Petrov, and C.G. Krespan J. Fluorine Chem. 102 2000 199 204
22. X.-H. Huang, P.Y. He, and G.Q. Shi. J. Org. Chem. 65 2000 627 629
23. H. Ueki, T. Chiba, T. Yamazaki, and T. Kitazume Tetrahedron 61 2005 11141 11147
24. J. Ichikawa, Y. Wada, M. Fujiwara, and K. Sakoda Synthesis 2002 1917 1936
25. K.W. Chi, H.A. Kim, G.G. Furin, E.L. Zhuzhgov, and N. Protzuk J. Fluorine Chem. 110 2001 11 20
26. Y. Wada, J. Ichikawa, T. Katsume, T. Nohiro, T. Okauchi, and T. Minami Bull. Chem. Soc. Jpn. 74 2001 971 977
27. J. Ichikawa, M. Fujiwara, Y. Wada, T. Okauchi, and T. Minami Chem. Commun. 2000 1887 1888
28. P.L. Coe, J. Burdon, and I.B. Haslock J. Fluorine Chem. 102 2000 43 50
29. A.V. Shastin, V.G. Nenajdenko, V.M. Muzalevskiy, E.S. Balenkova, R. Froehlich, and G. Haufe Tetrahedron 64 2008 9725 9732
30. J. Ichikawa, R. Nadano, T. Mori, and Y. Wada Org. Synth. 83 2006 111 120
31. C.M. Timperley, M.J. Waters, and J.A. Greenall J. Fluorine Chem. 127 2006 249 256
32. C.M. Timperley J. Fluorine Chem. 125 2004 685 693
33. H. Wojtzowicz-Rajchel, H. Koroniak, and A. Katrusiak Eur. J. Org. Chem. 2008 368 376
34. J. Ichikawa, Y. Wada, H. Kuroki, J. Mihara, and R. Nadano Org. Biomol. Chem. 5 2007 3956 3962
35. H. Wojtowicz-Rajchel, M. Migas, and H. Koroniak J. Org. Chem 71 2006 8842 8846
36. H. Koroniak, J. Walkowiak, K. Grys, A. Rajchel, A. Alty, and R. Du Boisson J. Fluorine Chem. 127 2006 1245 1251
37. J. Ichikawa, K. Sakoda, H. Moriyama, and Y. Wada Synthesis 2006 1590 1598
38. V.V. Rudyuk, D.V. Fedyuk, and L.M. Yagupolskii J. Fluorine Chem 125 2004 1465 1471
39. N.K. Park, B.T. Kim, S.S. Moon, S.L. Jeon, and I.H. Jeong Tetrahedron 60 2004 7943 7949
40. J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki Org. Lett 5 2003 1455 1458
41. For Diels-Alder reaction with dienes, see F. Chanteau, M. Essers, R. Plantier-Royon, G. Haufe, and C. Portella Tetrahedron Lett. 43 2002 1677 1680
42. T. Umemoto, Y. Kuriu, S.I. Nakayama, and O. Miyano Tetrahedron Lett. 23 1982 1471 1474
43. For Michael-type addition reaction with organocopper reagents, see K. Sano, T. Fukuhara, and S. Hara J. Fluorine Chem. 139 2009 708 713
44. J. Ichikawa, N. Yokota, M. Kobayashi, and T. Minami Synlett 1993 186 188
45. For the synthesis of fluorine-containing heterocyclic compounds, see J.T. Liu, and H.J. Lu Chin. J. Chem 20 2002 1330 1333
46. J.T. Liu, and H.J. Lu J. Fluorine Chem 111 2001 207 212
47. J. Ichikawa, M. Kobayashi, Y. Noda, N. Yokota, K. Amano, and T. Minami J. Org. Chem 61 1996 2763 2769
48. T. Ishihara, Y. Yamasaki, and T. Ando Tetrahedron Lett. 27 1986 2879 2880
49. D.C. England, and J.S. Piecara J. Fluorine Chem. 28 1985 417 423
50. For selected reports on applications of organofluorine compounds, see: J.P. Bégué, and D. Bonnet-Delpon J. Fluorine Chem. 127 2006 992 1012
51. C. Isanbor, and D. O'Hagen J. Fluorine Chem. 127 2006 303 319
52. K. Morimoto, and M. Irie Chem. Commun. 2005 3895 3905
53. R. Miethchen J. Fluorine Chem. 125 2004 895 901
54. For the reaction of perfluorocyclopentene, see: S. Yamada, E. Ishii, T. Konno, and T. Ishihara Tetrahedron 64 2008 4215 4223
55. S. Yamada, E. Ishii, T. Konno, and T. Ishihara Org. Biomol. Chem. 5 2007 1442 1449
56. S. Yamada, T. Konno, T. Ishihara, and H. Yamanaka J. Fluorine Chem. 126 2005 125 133
57. For the reaction of α,β,β-trifluoroacrylic ester, see: S. Yamada, M. Noma, K. Hondo, T. Konno, and T. Ishihara J. Org. Chem. 73 2008 522 528
58. S. Yamada, M. Noma, T. Konno, T. Ishihara, and H. Yamanaka Org. Lett. 8 2006 843 845
59. For the reaction of α,β,β-trifluorovinyl sulfone, see: S. Yamada, K. Shimoji, T. Takahashi, T. Konno, and T. Ishihara Chem. Asian J. 5 2010 1846 1853
60. S. Yamada, T. Takahashi, T. Konno, and T. Ishihara Chem. Commun. 2007 3679 3681
61. T. Ishihara, T. Maekawa, Y. Yamasaki, and T. Ando J. Fluorine Chem. 34 1987 323 335
62. T. Ishihara, Y. Yamasaki, and T. Ando Tetrahedron Lett. 27 1986 2879 2880
63. We revealed that the addition-elimination products were formed as a sole product when α,β,β-trifluoroacrylate was treated with Grignard reagents in the presence of Cu(I) salt, see: refs. [9d] and [9e].
64. It was expected that the reductive elimination of R-CuX was promoted by the addition of Lewis base like HMPA, DMF and TMSCl.
65. For related reports on the preparation of organocopper reagents by the treatment of organozinc reagents with CuCN2LiCl, see: M.J. Rozema, S. AchyuthaRao, and P. Knochel J. Org. Chem. 57 1992 1956 1958
66. S. AchyuthaRao, and P. Knochel J. Am. Chem. Soc. 113 1991 5735 5741
67. P. Knochel, M.C.P. Yeh, S.C. Berk, and J. Talbert J. Org. Chem. 53 1988 2390 2392
68. The formation of the homo-coupling product could be explained by a competitive reductive elimination step of the divinylcuprate formed after transmetallation. The similar results were reported in the following paper, see: J. Thibonnet, A. Duchêne, J.L. Parrain, and M. Abarbri J. Org. Chem 69 2004 4262 4264
69. Suzuki-Miyaura cross-coupling was conducted according to reported procedure with a similar substrate, see: T. Konno, T. Takehana, J. Chae, T. Ishihara, and H. Yamanaka J. Org. Chem. 69 2004 2188 2190
70. For related reports on π-complex between transition metal and polyfluorinated alkenes, see: T. Braun, D. Noveski, B. Neumann, and H.G. Stammler Angew. Chem. Int. Ed. 41 2002 2745 2748
71. M. Fujiwara, J. Ichikawa, T. Okauchi, and T. Minami Tetrahedron Lett. 40 1999 7261 7265
72. A.R. Siedle, and R.A. Newmark Organomet. 8 1989 1442 1450
73. For related reports on the interaction between metal and fluorine atom, see: T. Yamazaki J. Synth. Org. Chem. Jpn. 62 2004 911 918
74. T. Ishihara J. Synth Org. Chem. Jpn. 57 1999 313 322
75. T. Ooi, K. Furuta, and K. Maruoka Chem. Lett. 1998 817 818
76. T. Ooi, N. Kagoshima, D. Uraguchi, and K. Maruoka Tetrahedron Lett. 39 1998 7105 7108
77. T. Ooi, N. Kagoshima, and K. Maruoka J. Am. Chem. Soc. 119 1997 5754 5755
78. T. Ooi, D. Uraguchi, N. Kagoshima, and K. Maruoka Tetrahedron Lett. 38 1997 5679 5682
79. T. Yamazaki, and T. Kitazume J. Synth. Org. Chem. Jpn. 54 1996 665 674
80. T. Yamazaki, N. Shinohara, T. Kitazume, and S. Sato J. Org. Chem. 60 1995 8140 8141
81. T. Hanamoto, and T. Fuchikami J. Org. Chem. 55 1990 4969 4971
82. T. Yamazaki, N. Shinohara, T. Kitazume, and S. Sato J. Fluorine Chem. 97 1999 91 96
83. T. Yamazaki, H. Umetani, and T. Kitazume Israel J. Chem. 39 1999 193 205
84. T. Yamazaki, H. Umetani, and T. Kitazume Tetrahedron Lett. 38 1997 6705 6708
85. The addition-elimination product observed in some cases might be formed due to the high migration abilities of electron-rich aryl and alkyl groups.