Pd(DIPHOS)2-catalyzed cross-coupling reactions of organoborons with free or polymer-bound aryl halides

Organic Letters

Volumn 2, Issue 7, 2000, Pages 879-882

  De, Dibyendu ^a   Krogstad, Donald J ^a  

^a TULANE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIS(1,2 BIS(DIPHENYLPHOSPHINO)ETHANE)PALLADIUM; BIS(1,2-BIS(DIPHENYLPHOSPHINO)ETHANE)PALLADIUM; BORON DERIVATIVE; HALOGENATED HYDROCARBON; ORGANOMETALLIC COMPOUND; ORGANOPHOSPHORUS COMPOUND; PALLADIUM; POLYMER;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

BORON COMPOUNDS; CATALYSIS; HYDROCARBONS, HALOGENATED; ORGANOMETALLIC COMPOUNDS; ORGANOPHOSPHORUS COMPOUNDS; PALLADIUM; POLYMERS;

EID: 0034611491     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991356m     Document Type: Article

References (35)

1. (a) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; John Wiley & Sons: Chichester, England, 1995.
2. (b) Tsuji, J. Organic Synthesis with Palladium compounds; Springer-Verlag: Berlin, 1980.
3. (a) Suzuki, A. Metal-Catalyzed Cross Coupling Reactions; Driederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
4. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
5. (c) Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972.
6. (d) Smith, G. B.; Dezeny, G. C.; Hughes, D. L.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1994, 59, 8156.
7. (e) Moreno-Manas, M.; Perez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346.
8. (a) Miyaura, N.; Suginome, H.; Suzuki, A. Tetrahedron Lett. 1983, 24, 1527.
9. (b) Kobayashi, Y.; Shimazaki, T.; Taguchi, H.; Sato, F. J. Org. Chem. 1990, 55, 5324.
10. (c) Shieh, W. C.; Carlson, J. A. J. Org. Chem. 1992, 57, 379.
11. (a) Thompson, L. A.; Moore, F. L.; Moon, Y.-C.; Ellman, J. A. J. Org. Chem. 1998, 63, 2066.
12. (b) Lorsbach, B. A.; Bagdanoff, J. T.; Miller, R. B.; Kurth, M. J. J. Org. Chem. 1998, 63, 2244.
13. (c) Bleicher, K. H.; Wareing, J. R. Tetrahedron Lett. 1998, 39, 4587.
14. (d) Brown, S. D.; Armstrong, R. W. J. Org. Chem. 1997, 62, 7076.
15. (e) Koh, J. S.; Ellman, J. A. J. Org. Chem. 1996, 61, 4494.
16. Leadbeater, N. E.; Ressouly, S. M. Tetrahedron 1999, 55, 11889.
17. (a) Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531.
18. (b) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009.
19. (a) Genet, J. P.; Balabane, M.; Backvall, J. E.; Nystrom, J. E. Tetrahedron Lett. 1983, 24, 2745.
20. (b) Ferrona, D.; Genet, J. P.; Kiolle, R. Tetrahedron Lett. 1986, 27, 23.
21. (c) Unyoke, T.; Akihisa, M.; Go, H. Bull. Chem. Soc. Jpn. 1972, 45, 1183.
22. 2 {bis(triphenyl-phosphine)palladium dichloride}.
23. (a) Miyaura, N.; Ishiyama, T.; Sasaki, H.; Ishikawa, M.; Satoh, M.; Suzuki, A. J. Am. Chem. Soc. 1989, 111, 314.
24. (b) Ali, N. M.; McKillop, A.; Mitchell, M. B.; Rebelo, R.; Wallbank, P. J. Tetrahedron Lett. 1992, 48, 8117.
25. Yasuda, N.; Xavier, L.; Rieger, D. L.; Li, Y.; DeDamp, A. E.; Dolling, U. H. Tetrahedron Lett. 1993, 34, 3211.
26. (a) Giroux, A.; Han, Y.; Prasit, P. Tetrahedron Lett. 1997, 38, 3841.
27. (b) Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508.
28. 2) or by being passed through a short column of silica gel (5-10% EtOAc-petroleum ether) to obtain the desired product in 60-96% yield.
29. Grushin, V. V.; Alper, H. Organometallics 1993, 12, 1890.
30. Kang, S. K.; Lee, H. W.; Jang, S. B.; Ho, P. S. J. Org. Chem. 1996, 61, 4720.
31. Wright, S. W.; Hageman, D. L.; McClure, L. D. J. Org. Chem. 1994, 59, 6095.
32. (a) Han, H.; Wolfe, M. M.; Brenner, S.; Janda, K. D. Proc. Natl. Acad. Sci. U.S.A. 1995, 91, 11422.
33. (b) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489.
34. Blettner, C. G.; Konig, W. A.; Stenzel, W.; Scotten, T. Synlett 1998, 295.
35. 2O.