Transition metal-catalyzed C-C bond formation reactions using alkyl halides

Bulletin of the Chemical Society of Japan

Volumn 79, Issue 5, 2006, Pages 663-672

  Terao, Jun ^a   Kambe, Nobuaki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; CHEMICAL BONDS; HALOGEN COMPOUNDS;

ALKYL HALIDES; CARBON SOURCES; CATALYTIC SPECIES;

TRANSITION METALS;

1,3 BUTADIENE; ALKENE; ALKYL GROUP; ALLYL COMPOUND; CARBON; ETHER; FLUORIDE; HALIDE; NICKEL; STYRENE DERIVATIVE; TITANOCENE; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; ELECTRON TRANSPORT; GRIGNARD REACTION;

EID: 33746618592     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.79.663     Document Type: Article

References (64)

1. For reviews of transition metal-catalyzed cross-coupling reactions, see: a) Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., ed. by A. de Meijere, F. Diederich, Wiley-VCH, Weinheim, 2004.
2. b) Metal-Catalyzed Cross-Coupling Reactions, ed. by F. Diederich, P. J. Stang, Wiley-VCH, Weinheim, 1998.
3. c) Handbook of Organopalladium Chemistry for Organic Synthesis, ed. by E. Negishi, A. de Meijere, Wiley-Interscience, New York, 2002, p. 1669.
4. J. Terao, K. Torii, K. Saito, N. Kambe, A. Baba, N. Sonoda, Angew. Chem., Int. Ed. 1998, 37, 2653.
5. J. Terao, T. Watanabe, K. Saito, N. Kambe, N. Sonoda, Tetrahedron Lett. 1998, 39, 9201.
6. a) E. Negishi, F. E. Cederbaum, T. Takahashi, Tetrahedron Lett. 1986, 27, 2829.
7. b) F. Soleil, R. Choukroun, J. Am. Chem. Soc. 1997, 119, 2938.
8. c) V. K. Dioumaev, J. F. Harrod, Organometallics 1997, 16, 1452.
9. 2 with 3 molar amounts of EtMgBr, see: T. Takahashi, N. Suzuki, M. Kageyama, Y. Nitto, M. Saburi, E. Negishi, Chem. Lett. 1991, 1579.
10. Reactivities of alkyl groups on Zr as β-hydrogen donors, see: E. Negishi, T. Nguyen, J. P. Maye, D. Choueiri, N. Suzuki, T. Takahashi, Chem. Lett. 1992, 2367.
11. J. Terao, S. A. Begum, A. Oda, N. Kambe, Synlett 2005, 1783.
12. J. Terao, H. Watabe, H. Watanabe, N. Kambe, Adv. Synth. Catal. 2004, 346, 1674.
13. a) G. M. Whitesides, C. P. Casey, J. K. Krieger, J. Am. Chem. Soc. 1971, 93, 1379.
14. 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. 1981, 103, 6460.
15. a) J. J. Eisch, K. R. Im, J. Organomet. Chem. 1977, 139, C45.
16. b) T. Yamamoto, J. Ishizu, A. Yamamoto, Chem. Lett. 1979, 1385.
17. c) T. Yamamoto, J. Ishizu, A. Yamamoto, J. Am. Chem. Soc. 1981, 103, 6863.
18. J. Terao, N. Kambe, N. Sonoda, Tetrahedron Lett. 1998, 39, 9697.
19. J. Terao, H. Watabe, N. Kambe, J. Am. Chem. Soc. 2005, 127, 3656.
20. J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222.
21. For magnesium nickelate complexes, see: W. Kaschube, K. R. Pörschke, K. Angermund, C. Krüger, G. Wilke, Chem. Ber. 1988, 121, 1921.
22. J. Terao, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2003, 125, 5646.
23. J. Terao, K. Saito, S. Nii, N. Kambe, N. Sonoda, J. Am. Chem. Soc. 1998, 120, 11822.
24. H. A. Martin, F. Jellinek, J. Organomet. Chem. 1968, 12, 149.
25. 2Tin-Bu, see: a) E. Klei, J. H. Telgen, J. H. Teuben, J. Organomet. Chem. 1981, 209, 297.
26. 2TiCl with n-PrMgBr, see: b) G. A. Luinstra, L. C. Cate, H. J. Heeres, J. W. Pattiasina, A. Meetsma, J. H. Teuben, Organometallics 1991, 10, 3227.
27. 2Ti along with a 1:1 mixture of n-butane and butenes: J. X. McDermott, M. E. Wilson, G. M. Whitesides, J. Am. Chem. Soc. 1976, 98, 6529.
28. iPrMgBr is known: Y. Gao, F. Sato, J. Chem. Soc., Chem. Commun. 1995, 659.
29. S. Nii, J. Terao, N. Kambe, J. Org. Chem. 2004, 69, 573.
30. a) J. Terao, N. Kambe, J. Synth. Org. Chem., Jpn. 2001, 59, 1044.
31. b) J. Terao, H. Watabe, M. Miyamoto, N. Kambe, Bull. Chem. Soc. Jpn. 2003, 76, 2209.
32. In terms of this type of transformations using alkyl halides regardless of the mechanisms, several catalytic systems have been accomplished by the aid of late transition metals, see: a) S. Bräse, B. Waegell, A. de Meijere, Synthesis 1998, 148.
33. b) S. A. Lebedev, V. S. Lopatina, R. R. Shifrina, E. S. Petrov, I. P. Beletskaya, Izv. Akad. Nauk SSSR 1983, 10, 2414.
34. c) S. A. Lebedev, V. S. Lopatina, T. V. Luk'yanova, S. S. Berestova, R. R. Shifrina, N. N. Shapet'ko, E. S. Petrov, I. P. Beletskaya, Izv. Akad. Nauk SSSR 1985, 22, 652.
35. d) S. A. Lebedev, V. S. Lopatina, E. S. Petrov, I. P. Beletskaya, J. Organomet. Chem. 1988, 344, 253.
36. e) B. P. Branchaud, W. D. Detlefsen, Tetrahedron Lett. 1991, 32, 6273.
37. f) Y. Ikeda, T. Nakamura, H. Yorimitsu, K. Oshima, J. Am. Chem. Soc. 2002, 124, 6514.
38. g) T. Fujioka, T. Nakamura, H. Yorimitsu, K. Oshima, Org. Lett. 2002, 4, 2257.
39. h) Y. Ikeda, H. Yorimitsu, H. Shinokubo, K. Oshima, Adv. Synth. Catal. 2004, 346, 1631.
40. J. Terao, S. Nii, F. A. Chowdhury, A. Nakamura, N. Kambe, Adv. Synth. Catal. 2004, 346, 905.
41. 0 may proceed via a radical pathway, see: C. W. Weston, A. W. Verstuyft, J. H. Nelson, H. B. Jonassen, Inorg. Chem. 1977, 16, 1313.
42. International symposium on 30 years of the cross-coupling reaction: K. Tamao, T. Hiyama, E. Negishi, J. Organomet. Chem. 2002, 653, 1.
43. For recent reviews of transition metal-catalyzed cross-coupling reactions using alkyl halides, see: a) D. J. Cárdenas, Angew. Chem., Int. Ed. 1999, 38, 3018.
44. b) T.-Y. Luh, M.-K. Leung, K.-T. Wong, Chem. Rev. 2000, 100, 3187.
45. c) D. J. Cárdenas, Angew. Chem., Int. Ed. 2003, 42, 384.
46. d) M. R. Netherton, G. C. Fu, Adv. Synth. Catal. 2004, 346, 1525.
47. e) J. Terao, N. Kambe, J. Synth. Org. Chem., Jpn. 2004, 62, 1192.
48. f) A. C. Frisch, M. Beller, Angew. Chem., Int. Ed. 2005, 44, 674.
49. J. Terao, H. Todo, H. Watanabe, N. Kambe, Angew. Chem., Int. Ed. 2004, 43, 6180.
50. J. Terao, Y. Naitoh, H. Kuniyasu, N. Kambe, Chem. Lett. 2003, 32, 890.
51. 3-octadienediylnickel complex or a mixture of these species, see: R. Benn, B. Büssemeier, S. Holle, P. W. Jolly, R. Mynott, I. Tkatchenko, G. Wilke, J. Organomet. Chem. 1985, 279, 63.
52. 3- octadienediyl(phenyl)nickelate complex has been reported, see: S. Holle, P. W. Jolly, R. Mynott, R. Z. Salz, Z. Naturforsch., B: Anorg. Chem., Org. Chem. 1982, 37, 675.
53. 3- octadienediylnickelate complexes show unique catalytic activity for carbosilylation of 1,3-butadienes with chlorosilanes and Grignard reagents, see: J. Terao, A. Oda, A. Ikumi, A. Nakamura, H. Kuniyasu, N. Kambe, Angew. Chem., Int. Ed. 2003, 42, 3412.
54. Recent reviews for activation and functionalization of C-F bonds, see: a) S. Murai, Activation of Unreactive Bonds and Organic Synthesis, Springer, New York, 1999, p. 243.
55. b) T. Hiyama, Organofluorine Compounds Chemistry and Applications, Springer, New York, 2000.
56. 3 as the catalyst: a) T. Ooi, D. Uraguchi, N. Kagoshima, K. Maruoka, Tetrahedron Lett. 1997, 38, 5679.
57. b) K. Hirano, K. Fujita, H. Yorimitsu, H. Shinokubo, K. Oshima, Tetrahedron Lett. 2004, 45, 2555.
58. c) K. Hirano, H. Yorimitsu, K. Oshima, Org. Lett. 2004, 6, 4873.
59. d) M. Namavari, N. Satyamurthy, J. R. Barrio, J. Fluorine Chem. 1995, 72, 89.
60. e) G. A. Olah, S. C. Narang, L. D. Field, J. Org. Chem. 1981, 46, 3727.
61. For structures and stabilities of nickel complexes involved in cyclo-oligomerization of 1,3-butadiene, see: S. Tobisch, Adv. Organomet. Chem. 2003, 49, 167, and references therein.
62. For Ni-mediated cyclization of 1,3,8,10-tetraenes, see: a) P. A. Wender, M. J. Tebbe, Synthesis 1991, 1089, and references therein.
63. b) M. Takimoto, M. Mori, J. Am. Chem. Soc. 2004, 124, 10008.
64. A. E. Jensen, P. Knochel, J. Org. Chem. 2002, 67, 79.