A new ketone synthesis by palladium-catalyzed cross-coupling reactions of esters with organoboron compounds

Organic Letters

Volumn 6, Issue 20, 2004, Pages 3597-3599

  Tatamidani, Hiroto ^a   Kakiuchi, Fumitoshi ^a   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; KETONE; ORGANOBORON DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CROSS COUPLING REACTION; PRODUCTIVITY; SYNTHESIS;

EID: 6444237049     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048513o     Document Type: Article

References (35)

1. For recent reviews on cross-coupling, see: Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, U.K., 1995; pp 290-422. Metal-catalyzed Cross-coupling Reactions; Diedrich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998. Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
2. For recent reviews on cross-coupling, see: Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, U.K., 1995; pp 290-422. Metal-catalyzed Cross-coupling Reactions; Diedrich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998. Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
3. For recent reviews on cross-coupling, see: Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, U.K., 1995; pp 290-422. Metal-catalyzed Cross-coupling Reactions; Diedrich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998. Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
4. For recent reviews on the Suzuki-Miyaura coupling, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. Miyaura, N. J. Organomet. Chem. 2002, 653, 54. Suzuki, A. J. Organomet. Chem. 2002, 653, 83. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633. Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
5. For recent reviews on the Suzuki-Miyaura coupling, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. Miyaura, N. J. Organomet. Chem. 2002, 653, 54. Suzuki, A. J. Organomet. Chem. 2002, 653, 83. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633. Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
6. For recent reviews on the Suzuki-Miyaura coupling, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. Miyaura, N. J. Organomet. Chem. 2002, 653, 54. Suzuki, A. J. Organomet. Chem. 2002, 653, 83. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633. Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
7. For recent reviews on the Suzuki-Miyaura coupling, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. Miyaura, N. J. Organomet. Chem. 2002, 653, 54. Suzuki, A. J. Organomet. Chem. 2002, 653, 83. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633. Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
8. For recent reviews on the Suzuki-Miyaura coupling, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. Miyaura, N. J. Organomet. Chem. 2002, 653, 54. Suzuki, A. J. Organomet. Chem. 2002, 653, 83. Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633. Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
9. Ishiyama, T.; Miyaura, N.; Suzuki, A. Bull. Chem. Soc. Jpn. 1991, 64, 1999.
10. (a) Cho, C. S.; Itotani, K.; Uemura, S. J. Organomet. Chem. 1993, 443, 253.
11. (b) Bumagin, N. A.; Bykov, V. V. Tetrahedron 1997, 53, 14437.
12. (c) Bumagin, N. A.; Korolev, D. N. Tetrahedron Lett. 1999, 40, 3057.
13. (d) Haddach, M.; McCarthy, J. R. Tetrahedron Lett. 1999, 40, 3109.
14. (e) Kabalka, G. W.; Malladi, R. R.; Tejedor, D.; Kelley, S. Tetrahedron Lett. 2000, 41, 999.
15. (f) Chen, H.; Deng, M.-Z. Org. Lett. 2000, 2, 1649.
16. (g) Wang, J.-X.; Wei, B.; Hu, Y.; Liu, Z.; Yang, Y. Synth. Commun. 2001, 31, 3885.
17. (h) Urawa, Y.; Ogura, K. Tetrahedron Lett. 2003, 44, 271.
18. (i) Urakawa, Y.; Nishiura, K.; Souda, S.; Ogura, K. Synthesis 2003, 2882.
19. Zapf, A. Angew. Chem., Int. Ed. 2003, 42, 5394.
20. Goossen, L. J.; Ghosh, K. Eur. J. Org. Chem. 2002, 3254 and references therein.
21. Kakino, R.; Narahashi, H.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2002, 75, 1333 and references therein..
22. Zeysing, B.; Gosch, C.; Terfort, A. Org. Lett. 2000, 2, 1843.
23. (a) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2000, 2, 3229.
24. (b) Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260.
25. (c) Yu, Y.; Liebeskind, L. S. J. Org. Chem. 2004, 69, 3554.
26. Kakino, R.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2001, 74, 371.
27. Tatamidani, H.; Yokota, K.; Kakiuchi, F.; Chatani, N. J. Org. Chem. 2004, 69, 5615.
28. (a) Onaka, M.; Goto, T.; Mukaiyama, T. Chem. Lett. 1979, 1483.
29. (b) Araki, M.; Sakata, S.; Takei, H.; Mukaiyam, T. Bull. Chem. Soc. Jpn. 1974, 47, 1777.
30. (c) Onaka, M.; Matsuoka, Y.; Mukaiyama, T. Chem. Lett. 1981, 531.
31. (a) Dutta, A. S.; Morley, J. S. J. Chem. Soc. C 1971, 17, 2896.
32. (b) Tsuboi, S.; Okada, Y. Chem. Pharm. Bull. 1989, 37, 46.
33. Netherton, M. R.; Dai, C.; Neuschütz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099.
34. Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
35. Mukaiyama reported the nickel-catalyzed coupling reaction of pyridyl ester with diethylzinc. They proposed the nucleophilic attack of ethylnickel spiecies derived from diethylzinc and nickel catalyst. See ref 12c.