Carbon-carbon bond-forming reactions using alkyl fluorides

Pure and Applied Chemistry

Volumn 80, Issue 5, 2008, Pages 941-951

  Terao, Jun ^a   Todo, Hirohisa ^a   Watabe, Hiroyasu ^a   Ikumi, Aki ^a   Shinohara, Yoshiaki ^a   Kambe, Nobuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Alkyl fluorides; Bond formation; Carbon carbon bond; Organoaluminum; Transition metal catalysts

Indexed keywords

EID: 44649131863     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200880050941     Document Type: Conference Paper

References (58)

1. Recent reviews for activation and substitution of C-F bonds, see: (a) S. Murai. In Activation of Unreactive Bonds and Organic Synthesis, pp. 243-269, Springer, New York (1999);
2. (b) T. Hiyama. In Organofluorine Compounds Chemistry and Applications, Springer, New York (2000).
3. (a) Y. Kiso, K. Tamao, M. Kumada. J. Organomet. Chem. 50, C12 (1973);
4. (b) M. Aizenberg, D. Milstein. Science 265, 359 (1994);
5. (c) G. B. Deacon, C. M. Forsyth, J. Sun. Tetrahedron Lett. 35, 1095 (1994);
6. (d) M. Aizenberg, D. Milstein. J. Am. Chem. Soc. 117, 8674 (1995);
7. (e) Y. Ishii, N. Chatani, S. Yorimitsu, S. Murai. Chem. Lett. 157 (1998);
8. (f) J. Y. Robert Jr., V. G. Vladimir. Organometallics 18, 294 (1999);
9. (g) H. Yang, H. Gao, J. R. Angelici. Organometallics 18, 2285 (1999);
10. (h) B. L. Edelbach, B. M. Kraft, W. D. Jones. J. Am. Chem. Soc. 121, 10327 (1999);
11. (i) T. G. Richmond. Angew. Chem., Int. Ed. 39, 3241 (2000);
12. (j) V. P. W. Böhm, C. W. K. Gstöttmayr, T. Weskamp, W. A. Herrmann. Angew. Chem., Int. Ed. 40, 3387 (2001).
13. (a) R. G. Harrison, T. G. Richmond. J. Am. Chem. Soc. 115, 5303 (1993);
14. (b) M. Weydert, R. A. Andersen, R. G. Bergmen. J. Am. Chem. Soc. 115, 8837 (1993);
15. (c) J. L. Kiplinger, T. G. Richmond. Chem. Commun. 1115 (1996);
16. (d) B. L. Edelbach, W D. Jones. J. Am. Chem. Soc. 119, 7734 (1997).
17. (a) J. L. Kiplinger, T. G. Richmond. J. Am. Chem. Soc. 118, 1805 (1996);
18. (b) J. Burdeniuc, R. H. Crabtree. J. Am. Chem. Soc. 118, 2525 (1996);
19. (c) J. Burdeniuc, R. H. Crabtree. Organometallics 17, 1582 (1998);
20. (d) B. M. Kraft, R. J. Lachicotte, W. D. Jones. J. Am. Chem. Soc. 122, 8559 (2000).
21. 3)C-F bond, see: (a) T. Hatakeyama, S. Ito, M. Nakamura, E. Nakamura. J. Am. Chem. Soc 127, 14192 (2005);
22. (b) K. Fuchibe, T. Akiyama. J. Am. Chem. Soc. 128, 1434 (2006);
23. (c) K. Fuchibe, K. Mitomi, T. Akiyama. Chem. Lett. 36, 24 (2007).
24. Nb-catalyzed reduction of α,α,α-trifluorotoluenes, see: K. Fuchibe, Y. Ohshima, K. Mitomi, T. Akiyama. Org. Lett. 9, 1497 (2007).
25. J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe. J. Am. Chem. Soc. 124, 4222 (2002).
26. (a) For the history and recent development of transition-metal-catalyzed cross-coupling reactions, see: International Symposium on 30 years of the Cross-coupling Reaction, J. Organomet. Chem. 653, 1 (2002);
27. (b) F. Diederich, P. J. Stang (Eds.). Metal-catalyzed Cross-coupling Reactions, Wiley-VCH, New York (1998).
28. J. Terao, A. Ikumi, H. Kuniyasu, N. Kambe. J. Am. Chem. Soc. 125, 5646 (2003).
29. S. Tobisch. Adv. Organomet. Chem. 49, 167 (2003).
30. For Ni-mediated cyclization of 1,3,8,10-tetraenes, see: (a) P. A. Wender, M. J. Tebbe. Synthesis 1089 (1991);
31. (b) M. Takimoto, M. Mori. J. Am. Chem. Soc. 124, 10008 (2002).
32. J. Terao, H. Todo, H. Watanabe, A. Ikumi, N. Kambe. Angew. Chem., Int. Ed. 43, 6180 (2004).
33. J. Terao, H. Todo, S. A. Begum, H. Kuniyasu, N. Kambe. Angew. Chem., Int. Ed. 46, 2086 (2007).
34. J. Terao, H. Watabe, N. Kambe. J. Am. Chem. Soc. 127, 3656 (2005).
35. (a) G. M. Whitesides, C. P. Casey. J. K. Krieger. J. Am. Chem. Soc. 93, 1379 (1971);
36. (b) M. F. Semmelhack, P. Helquist, L. D. Jones, L. Keller, L. Mendelson, L. S. Ryono, J. G. Smith, R. D. Stauffer. J. Am. Chem. Soc. 103, 6460 (1981).
37. W. Kaschube, K. R. Pörschke. K. Angermund, C. Krüger. G. Wilke. Chem. Ber. 121, 1921 (1988).
38. J. Terao, K. Torii, K. Saito, N. Kambe, A. Baba, N. Sonoda. Angew. Chem., Int. Ed. 37, 2653 (1998).
39. J. Terao, T. Watanabe, K. Saito, N. Kambe, N. Sonoda. Tetrahedron Lett. 39, 9201 (1998).
40. (a) E. Negishi, F. E. Cederbaum, T. Takahashi. Tetrahedron Lett. 27, 2829 (1986);
41. (b) F. Soleil, R. Choukroun. J. Am. Chem. Soc. 119, 2938 (1997);
42. (c) V K. Dioumaev, J. F. Harrod. Organometallics 16, 1452 (1997).
43. T. Takahashi, N. Suzuki, M. Kageyama, Y. Nitto, M. Saburi, E. Negish. Chem. Lett. 1579 (1991).
44. E. Negish, T. Nguyen, J. P. Maye, D. Choueiri, N. Suzuki, T. Takahashi. Chem. Lett. 2367 (1992).
45. J. Terao, S. A. Begum, A. Oda, N. Kambe. Synlett 1783 (2005).
46. (a) P. Tarrant, R. N. Bull. J. Fluorine Chem. 40, 201 (1988);
47. (b) B. Košmrlj, B. Kralj, B. Šket. Tetrahedron Lett. 36, 7921 (1995);
48. (c) G. H. Posner, G. M. Gurria, K. A. Babiak. J. Org. Chem. 42, 3173 (1997);
49. (d) T. Ooi, D. Uraguchi, N. Kagoshima, K. Maruoka. Tetrahedron Lett. 38, 5679 (1997);
50. (e) K. Toshima. Carbohydr. Res. 327, 15 (2000);
51. (f) V. A. Petrov. J. Fluorine Chem. 117, 23 (2002);
52. (g) M. Yoshimatsu, M. Kawamoto, K. Gotoh. Eur. J. Org. Chem. 14, 2884 (2005).
53. (a) J. S. Filippo Jr., A. F. Sowinski, L. J. Romano. J. Org. Chem. 40, 3295 (1975);
54. (b) G. A. Olah, S. C. Narang, L. D. Field. J. Org. Chem. 46, 3727 (1981);
55. (c) M. Namavari, N. Satyamurthy, J. R. Barrio. J. Fluorine Chem. 72, 89 (1995).
56. G. H. Posner, S. R. Haines. Tetrahedron Lett. 26, 1823 (1985).
57. K. Hirano, K. Fujita, H. Yorimitsu, H. Shinokubo, K. Oshima. Tetrahedron Lett. 45, 2555 (2004).
58. J. Terao, S. A. Begum, Y. Shinohara, M. Tomita, Y. Naitoh, N. Kambe. Chem. Commun. 855 (2007).