Palladium-catalyzed cross-coupling reactions of (2-pyridyl) allyldimethylsilanes with aryl iodides

Organic Letters

Volumn 8, Issue 4, 2006, Pages 729-731

  Nokami, Toshiki ^a   Tomida, Yutaka ^a   Kamei, Toshiyuki ^a   Itami, Kenichiro ^a,b   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33644773385     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052961u     Document Type: Article

References (43)

1. Recent reviews for pyridine syntheses: (a) Henry, G. D. Tetrahedron 2004, 60, 6043.
2. (b) Tyrrell, E.; Brookes, P. Synthesis 2004, 469.
3. For recent metal-catalyzed reactions to synthesize pyridine derivatives, see: (c) Godula, K.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2005, 127, 3648.
4. (d) Jordan, R. F.; Taylor, D. F. J. Am. Chem. Soc. 1989, 111, 778.
5. (e) Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am. Chem. Soc. 1992, 114, 5888.
6. (f) Murakami, M.; Hori, S. J. Am. Chem. Soc. 2003, 125, 4720 and references therein.
7. (a) Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
8. Recent reviews for cross-coupling reactions using organosilicon compounds: (b) Hiyama, T.; Shirakawa, E. Top. Curr. Chem. 2002, 219, 61.
9. (c) Hiyama, T. J. Organomet. Chem. 2002, 653, 58.
10. (d) Denmark, S. E.; Sweis, R. F. Chem. Pharm. Bull. 2002, 50, 1531.
11. (Trialkylstannyl)pyridines are commercially available; see also ref 2a. In situ generation of (2-pyridyl)dichlorosilanes has been reported: (a) Hagiwara, E.; Kusumoto, T.; Hiyama, T. 76th National Meeting of the Chemical Society of Japan, Yokohama, 1999.
12. 2-Pyridylboron reagents have been reported: (b) Hodgson, P. B.; Salingue, F. H. Tetrahedron Lett. 2004, 45, 685. See also ref 1b.
13. Pierrat, P.; Gros, P.; Fort, Y. Org. Lett. 2005, 7, 697.
14. Biaryl syntheses using arylsilanes and pyridyl halides have been reported: (a) Hatanaka, Y.; Gouda, K.-i.; Okahara, Y.; Hiyama, T. Tetrahedron 1994, 50, 8301.
15. (b) Hagiwara, E.; Gouda, K.-i.; Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1997, 38, 439.
16. (c) Mowery, M. E.; Deshong, P. Org. Lett. 1999, 1, 2137.
17. (d) Lee, H. M.; Nolan, S. P. Org. Lett. 2000, 2, 2053.
18. (e) Sahoo, A. K.; Nakao, Y.; Hiyama, T. Chem. Lett. 2004, 33, 632.
19. (f) Sahoo, A. K.; Oda, T.; Nakao, Y.; Hiyama, T. Adv. Synth. Catal. 2004, 346, 1715.
20. (g) Wolf, C.; Lerebours, R. Org. Lett. 2004, 6, 1147.
21. Silicates can transfer the activated pyridyl group in excellent yields: (a) Seganish, W. M.; Deshong, P. J. Org. Chem. 2004, 69, 1137.
22. Recently, the (2-hydroxymethyl)phenyl group was developed as a reusable activating group of the silicon atom and can transfer 2-pyridyl group: (b) Nakao, Y.; Imanaka, H.; Sahoo, A. K.; Yada, A.; Hiyama, T. J. Am. Chem. Soc. 2005, 127, 6952. See also ref 3a.
23. (a) Itami, K.; Nokami, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 5600.
24. (b) Itami, K.; Nokami, T.; Ishimura, Y.; Mitsudo, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577.
25. Itami, K.; Kamei, T.; Yoshida, J. Unpublished results.
26. Itami, K.; Mineno, M.; Kamei, T.; Yoshida, J. Org. Lett. 2002, 4, 3635.
27. 4NF has been the most versatile fluoride ion source in cross-coupling reactions since Hiyama revealed its efficiency: Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1988, 54, 268. See also ref 2.
28. Palladium-catalyzed cross-coupling reactions using alkenyl- or arylsilanes in the presence of copper salts: (a) Suginome, M.; Kinugasa, H.; Ito, Y. Tetrahedron Lett. 1994, 35, 8635.
29. (b) Taguchi, H.; Ghoroku, K.; Tadaki, M.; Tsubouchi, A.; Takeda, T. J. Org. Chem. 2002, 67, 8450.
30. (c) Denmark, S. E.; Kobayashi, T. J. Org. Chem. 2003, 68, 5153.
31. (d) Denmark, S. E.; Baird, J. D. Org. Lett. 2004, 6, 3649. See also ref 6b.
32. Under the conditions reported by Gros, 2-pyridyltrimethylsilane did not give 2-pyridylbenzene either.
33. Palladium-catalyzed cross-coupling reactions using aryl- or alkynylsilanes in the presence of silver salts: (a) Hirabayashi, K.; Kawashima, J.; Nishihara, Y.; Mori, A.; Hiyama, T. Org. Lett. 1999, 1, 299.
34. (b) Hirabayashi, K.; Mori, A.; Kawashima, J.; Suguro, M.; Nishihara, Y.; Hiyama, T. J. Org. Chem. 2000, 65, 5342.
35. (c) Koseki, Y.; Omino, K.; Anzai, S.; Nagasaka, T. Tetrahedron Lett. 2000, 41, 2377.
36. Various substituents have been reported as potentially activating groups of silicon atom. (a) Denmark, S. E.; Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821.
37. (b) Hosoi, K.; Nozaki, K.; Hiyama, T. Chem. Lett. 2002, 138.
38. (c) Trost, B. M.; Machacek, M. R.; Ball, Z. T. Org. Lett. 2003, 5, 1895.
39. (d) Anderson, J. C.; Munday, R. H. J. Org. Chem. 2004, 69, 8971. See also refs 5e,f and 7.
40. Styrene, which is the cross-coupling product between the vinyl group and iodobenzene, was observed as a byproduct.
41. We reported syntheses and crystal structures of copper-(2-pyridyl) vinyldimethylsilane and copper-(2-pyridyl)allyldimethylsilane complexes: (a) Itami, K.; Ushiogi, Y.; Nokami, T.; Ohashi, Y.; Yoshida, J. Org. Lett. 2004, 6, 3695.
42. (b) Kamei, T.; Fujita, K.; Itami, K.; Yoshida, J. Org. Lett. 2005, 7, 4725.
43. Itami, K.; Kamei, T.; Mineno, M.; Yoshida, J. Chem. Lett. 2002, 1084.