Room-Temperature Ni(0)-Catalyzed Cross-Coupling Reactions of Aryl Arenesulfonates with Arylboronic Acids

Journal of the American Chemical Society

Volumn 126, Issue 10, 2004, Pages 3058-3059

  Tang, Zhen Yu ^a   Hu, Qiao Sheng ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; NICKEL; PALLADIUM; SULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CROSS COUPLING REACTION; OXIDATION; REACTION ANALYSIS; ROOM TEMPERATURE; SUZUKI REACTION; TEMPERATURE DEPENDENCE;

EID: 1642320259     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038752r     Document Type: Article

References (32)

1. For recent reviews: (a) Miyaura, N. Top. Curr. Chem. 2002, 219, 11-59.
2. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
3. For a recent review: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
4. Recent examples of the Suzuki cross-coupling reaction involving aryl chlorides as substrates: (a) Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem., Int. Ed. 2003, 41, 4746-4748.
5. (b) Hu, Q.-S.; Lu, Y.; Tang, Z.-Y.; Yu, H.-B. J. Am. Chem. Soc. 2003, 125, 2856-2857.
6. (c) Jensen, J. F.; Johannsen, M. Org. Lett. 2003, 5, 3025-3028.
7. (d) Altenhoff, G.; Goddard, R.; Lehmann, C. W.; Glorius, F. Angew. Chem., Int. Ed. 2003, 42, 3690-3693.
8. (e) Pickett, T. E.; Roca, F. X.; Richards, C. J. J. Org. Chem. 2003, 68, 2592-2599.
9. (f) Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866-2873.
10. (g) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553-5566.
11. The cross-coupling of one example of electron-deficient aryl tosylate with lithium arylborates was reported: Kobayashi, Y.; Mizojiri, R. Tetrahedron Lett. 1996, 37, 8531-8534.
12. Zim, D.; Lando, V. R.; Dupont, J.; Monteiro, A. L. Org. Lett. 2001, 3, 3049-3051.
13. Lakshman, M. K.; Thomson, P. F.; Nuqui, M. A.; Hilmer, J. H.; Sevova, N. ; Boggess, B. Org. Lett. 2002, 4, 1479-1482.
14. During the preparation of this manuscript, Buchwald reported a Pd-monophosphine catalyst for the Suzuki coupling of both electron-rich and electron-deficient aryl arenesulfonates at 80 °C: Ngyuen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11818-11819.
15. Suzuki-Miyaura coupling reactions involving aryl mesylates: (a) Percec, V.; Bae, J.-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 1060-1065.
16. Also see ref 4. Suzuki-Miyaura coupling reactions involving vinyl tosylates: (b) Wu, J.; Zhu, Q.; Wang, L.; Fathi, R.; Yang, Z. J. Org. Chem. 2003, 68, 670-673.
17. (c) Wu, J.; Wang, L.; Fathi, R.; Yang, Z. Tetrahedron Lett. 2002, 43, 4395-4397.
18. (d) Huffman, M. A.; Yasuda, N. Synlett 1999, 471-473.
19. For other coupling reactions involving aryl arenesulfonates: (a) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 8704-8705.
20. (b) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653-6655.
21. (c) Wu, J.; Liao Y.; Yang, Z. J. Org. Chem. 2003, 68, 3642-3645.
22. (d) Furstner, A.; Leitner, A.; Mendez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856-13863.
23. (e) Bolm, C.; Hildebrand, J. P.; Rudolph, J. Synthesis 2000, 911.
24. (f) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369-7370.
25. (g) Nagatsugi, F.; Uemura, K.; Nakashima, S.; Minoru, M.; Sasaki, S. Tetrahedron Lett. 1995, 36, 421-423.
26. (h) Badone, D.; Cecchi, R.; Guzzi, U. J. Org. Chem. 1992, 57, 6321-6323.
27. (a) Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413-2415.
28. (b) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550-9551.
29. (c) Old, D. A.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9772-9773.
30. For examples of modification of catalysts with additives: (a) Savarin, C.; Liebeskind, L. S. Org. Lett. 2001, 3, 2149-2152.
31. (b) Singh, U. K.; Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14104-14114.
32. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.