Suzuki coupling of heteroaromatic chlorides using highly electron-donating clickphos ligands

Synthesis

Volumn , Issue 18, 2009, Pages 3094-3098

  Spinella, Stephen M ^a   Guan, Zheng Hui ^a   Chen, Jian ^a   Zhang, Xumu ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

ClickPhos; Heteroaromatic chlorides; Palladium; Suzuki coupling

Indexed keywords

BORONIC ACID; CLICKPHOS; ELECTRON-DONATING; ELECTRON-RICH; HETEROAROMATIC CHLORIDES; HIGH YIELD; SUZUKI COUPLING; SUZUKI COUPLINGS; SUZUKI CROSS COUPLING; SUZUKI CROSS COUPLING REACTIONS;

LIGANDS; PALLADIUM;

CHLORINE COMPOUNDS;

AROMATIC COMPOUND; BORONIC ACID DERIVATIVE; CHLORIDE; PALLADIUM;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONTROLLED STUDY; ELECTRON; SUZUKI REACTION; SYNTHESIS;

EID: 70449382082     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216942     Document Type: Article

References (34)

1. Miyaura, N.; Suzuki, A. Chem. Rev. 1996, 95, 2457.
2. Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 1290.
3. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
4. Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, 1998,.
5. de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, 2004.
6. Dehmel, F.; Molander, G. A. J. Am. Chem. Soc. 2004, 33, 10313.
7. Durham, T. B.; Blanchard, N.; Savall, B.; Noel, A.; Roush, W. R. J. Am. Chem. Soc. 2006, 126, 9307.
8. Christmann, U.; Vilar, R. Angew. Chem. Int. Ed. 2005, 44, 366.
9. Miura, M. Angew. Chem. Int. Ed. 2004, 43, 2201.
10. Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
11. Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
12. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 124, 4020.
13. Netherton, M. R.; Dai, C.; Neuschutz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099.
14. Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 13662.
15. Kudo, N.; Perseghini, M.; Fu, G. C. Angew. Chem. Int. Ed. 2006, 45, 1282.
16. Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
17. Yin, J.; Rainka, M. P.; Zhang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162.
18. Nguyen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11818.
19. Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem. Int. Ed. 2004, 43, 1871.
20. Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
21. Billingsley, K. L.; Anderson, K. W.; Buchwald, S. L. Angew. Chem. Int. Ed. 2006, 45, 3484.
22. Billingsley, K.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3358.
23. Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem. Int. Ed. 2002, 41, 4746.
24. Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553.
25. Zapf, A.; Jackstell, R.; Rataboul, F.; Reirmeier, T.; Monsees, A.; Fuhrmann, C.; Shaikh, N.; Dingerdissen, U.; Beller, M. Chem. Commun. 2004, 38.
26. Harkal, S.; Rataboul, F.; Zapf, A.; Fuhrmann, C.; Reirmeier, T.; Monsees, A.; Beller, M. Adv. Synth. Catal. 2004, 346, 1742.
27. For a review, see: Zapf, A.; Beller, M. Chem. Commun. 2005, 431.
28. Dai, Q.; Gao, W.; Liu, D.; Zhang, X. Org. Lett. 2005, 7, 4907.
29. Dai, D.; Gao, W.; Liu, D.; Kapes, L. M.; Zhang, X. J. Org. Chem. 2006, 71, 3928.
30. Kudo, N.; Perseghini, M.; Fu, G. C. Angew. Chem. Int. Ed. 2006, 45, 1282.
31. Billingsley, K. L.; Anderson, K. W.; Buchwald, S. L. Angew. Chem. Int. Ed. 2006, 45, 3484.
32. Guram, A. S.; King, A. O.; Allen, J. G.; Wang, X.; Schenkel, L. B.; Chan, J.; Bunel, E. E.; Faul, M. M.; Larsen, R. D.; Martinelli, M. J.; Reider, P. J. Org. Lett. 2006, 8, 1787.
33. Billingsley, K.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3358.
34. Yamamoto, Y.; Takizawa, M.; Yu, X. Q.; Miyaura, N. Angew. Chem. Int. Ed. 2008, 47, 928.