Palladium(0)-catalyzed amination, stille coupling, and Suzuki coupling of electron-deficient aryl fluorides

Journal of the American Chemical Society

Volumn 125, Issue 7, 2003, Pages 1696-1697

  Kim, Young Mi ^a   Yu, Shu ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORIDE; N,N DIMETHYLFORMAMIDE; PALLADIUM;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; ELECTRON; OXIDATION; REACTION ANALYSIS;

EID: 0037442333     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028966t     Document Type: Article

References (17)

1. (a) Hegedus, L. S. In Organometallics in Synthesis: A Manual, 2nd ed.; Schlosser, M., Ed.; Wiley: New York, 2002; pp 1123-1217.
2. (b) Grushin, V. V. Chem.-Eur. J. 2002, 8, 1006-1014.
3. (a) Widdowson, D. A.; Wilhelm, R. Chem. Commun. 1999, 21, 2211-2212.
4. (b) Wilhelm, R.; Widdowson, D. A. J. Chem. Soc., Perkin Trans. 1 2000, 22, 3808-3814.
5. (c) Jakt, M.; Johannissen, L.; Rzepa, H. S.; Widdowson, D. A.; Wilhelm, R. J. Chem. Soc., Perkin Trans. 2 2002, 576-581.
6. (d) Wilhelm, R. Arenetricarbonylchromium(0) Complexes in Synthesis; Ph.D. Thesis; University of London, London, 2001. In Rene Wilhelm's thesis (Widdowson advisor), a single example of Suzuki coupling of phenyl boronic acid and 2,4-dinitrofluorobenzene was described.
7. (a) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158-1174.
8. (b) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028 and references therein.
9. (c) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., de Meijere, A., Eds.; Wiley: New York, 2002; pp 1051-1096.
10. (d) Singh, U. K.; Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc., 2002, 124, 14104-14114.
11. (e) Widenhoefer, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6504-6511.
12. (f) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 1232-1233.
13. Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469.
14. Raising the reaction temperature did not make any difference.
15. Sanger's reagent was not employed for safety considerations.
16. (a) Amatore, C.; Pfluger, F. Organometallics 1990, 9, 2276-2282.
17. (b) Jutand, A.; Mosleh, A. Organometallics 1995, 14, 1810-1817.