Effect of fluorine on palladium-catalyzed cross-coupling reactions of aryl bromides with trifluoromethyl aryl ketones via difluoroenol silyl or monofluoroenol silyl ethers

Chemical Communications

Volumn , Issue 34, 2007, Pages 3583-3585

  Guo, Yong ^a   Shreeve, Jean'ne M ^a  

^a UNIVERSITY OF IDAHO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMIDE; FLUORINE; FLUOROFORM; KETONE; PALLADIUM; SILANE; SILANE DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION;

EID: 34748820559     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b705137a     Document Type: Article

References (37)

1. Organofluorine Compounds: Chemistry and Applications, ed., T. Hiyama,, Springer, New York, 2000
2. Biomedical Frontiers of Fluorine Chemistry (ACS Symp. Ser.), ed., I. Ojima,,, J. R. McCarthy, and, J. T. Welch,, American Chemical Society, Washington DC, 1996, 639
3. J. Kollonitsch L. M. Perkins A. A. Patchett G. A. Doldouras S. Marburg D. E. Duggan A. L. Maycock S. D. Aster Nature 1978 274 906 908
4. F. M. D. Ismail J. Fluorine Chem. 2002 118 27 33
5. P. Jeschke ChemBioChem 2004 5 570 589
6. I. Pravst M. Zupan S. Stavber Synthesis 2005 3140 3146
7. J. Ramirez E. Fernandez Synthesis 2005 1698 1700
8. R. P. Singh U. Majumder J. M. Shreeve J. Org. Chem. 2001 66 6263 6267
9. T. B. Patrick J. J. Scheibel G. L. Cantrell J. Org. Chem. 1981 46 3917 3918
10. R. F. Merritt J. K. Ruff J. Org. Chem. 1965 30 328 331
11. J. Bornstein M. R. Borden F. Nunes H. I. Tarlin J. Am. Chem. Soc. 1963 85 1609 1615
12. I. Fleming R. S. Roberts S. C. Smith J. Chem. Soc., Perkin Trans. 1 1998 1215 1228
13. T. Brigaud P. Doussot C. Portella J. Chem. Soc., Chem. Commun. 1994 2117 2118
14. B. Jiang X. Zhang G. Shi Tetrahedron Lett. 2002 43 6819 6821
15. K. C. Nicolaou A. A. Estrada S. H. Lee G. C. Freestone Angew. Chem., Int. Ed. 2006 45 5364 5368
16. F. Jin Y. Xu W. Huang J. Chem. Soc., Chem. Commun. 1993 814 816
17. W. J. Chung J. T. Welch J. Fluorine Chem. 2004 125 543 548
18. Z.-M. Qiu D. J. Burton J. Org. Chem. 1995 60 5570 5578
19. G. K. S. Prakash J. Hu M. M. Alauddin P. S. Conti G. A. Olah J. Fluorine Chem. 2003 121 239 243
20. I. Kuwajima H. Urabe J. Am. Chem. Soc. 1982 104 6831 6833
21. I. T. Tetsuo V. H. Rawal Org. Lett. 2006 8 5725 5728
22. W. Su S. Raders J. G. Verkade X. Liao J. F. Hartwig Angew. Chem., Int. Ed. 2006 45 5852 5855
23. J. Chae J. Yun S. L. Buchwald Org. Lett. 2004 6 4809 4812
24. K. Uneyama H. Tanaka S. Kobayashi M. Shioyama H. Amii Org. Lett. 2004 6 2733 2736
25. H. Amii T. Kobayashi Y. Hatamoto K. Uneyama Chem. Commun. 1999 1323 1324
26. H. Amii and K. Uneyama, in Fluorine-Containing Synthons (ACS Symp. Ser.), ed., V. A. Soloshonok,, Oxford University Press, Oxford, 2005, ch. 27, pp. 455-475
27. K. Uneyama H. Amii J. Fluorine Chem. 2002 114 127 131
28. J. Yin D. S. Zarkowsky D. W. Thomas M. M. Zhao M. A. Huffman Org. Lett. 2004 6 1465 1468
29. W. J. Middleton E. M. Bingham J. Am. Chem. Soc. 1980 102 4845 4846
30. D.-Y. Zhou Q.-Y. Chen Chin. J. Chem. 2004 22 953 957
31. É. Bélanger K. Cantin O. Messe M. Tremblay J.-F. Paquin J. Am. Chem. Soc. 2007 129 1034 1035
32. S. L. Fraser M. Y. Antipin V. N. Khroustalyov V. V. Grushin J. Am. Chem. Soc. 1997 119 4769 4770
33. D. V. Yandulov N. T. Tran J. Am. Chem. Soc. 2007 129 1342 1358
34. Y. M. Kim S. Yu J. Am. Chem. Soc. 2003 125 1696 1697
35. T. Schaub M. Backes U. Radius J. Am. Chem. Soc. 2006 128 15964 15965
36. T. Braun R. N. Perutz Chem. Commun. 2002 2749 2757
37. T. Braun R. N. Perutz M. I. Sladek Chem. Commun. 2001 2254 2255