Copper-mediated fluorination of aryl iodides

Journal of the American Chemical Society

Volumn 134, Issue 26, 2012, Pages 10795-10798

  Fier, Patrick S ^a   Hartwig, John F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL FLUORIDES; ARYL IODIDES; BIOLOGICAL PROPERTIES; REDUCTIVE ELIMINATION;

AGRICULTURAL CHEMICALS; CHEMICAL REACTIONS; COPPER; FLUORINE; SILVER HALIDES;

FLUORINE COMPOUNDS;

AGRICULTURAL CHEMICAL; COPPER; FLUORIDE; IODIDE; POLYCYCLIC AROMATIC HYDROCARBON; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; FLUORINATION; FLUORINE NUCLEAR MAGNETIC RESONANCE; MOLECULAR PROBE; MOLECULAR STABILITY; SYNTHESIS;

BENZENE DERIVATIVES; COPPER; FLUORIDES; HALOGENATION; HYDROCARBONS, FLUORINATED; IODIDES; SILVER COMPOUNDS;

EID: 84863506671     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja304410x     Document Type: Article

References (32)

1. Olah, G. A.; Welch, J. T.; Vankar, Y. D.; Nojima, M.; Kerekes, I.; Olah, J. A. J. Org. Chem. 1979, 44, 3872
2. Adams, D. J.; Clark, J. H. Chem. Soc. Rev. 1999, 28, 225
3. Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470
4. Watson, D. A.; Su, M. J.; Teverovskiy, G.; Zhang, Y.; Garcia-Fortanet, J.; Kinzel, T.; Buchwald, S. L. Science 2009, 325, 1661
5. Tang, P. P.; Wang, W. K.; Ritter, T. J. Am. Chem. Soc. 2011, 133, 11482
6. Furuya, T.; Strom, A. E.; Ritter, T. J. Am. Chem. Soc. 2009, 131, 1662
7. Tang, P. P.; Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2010, 132, 12150
8. Furuya, T.; Kaiser, H. M.; Ritter, T. Angew. Chem., Int. Ed. 2008, 47, 5993
9. Furuya, T.; Ritter, T. Org. Lett. 2009, 11, 2860
10. Tang, P. P.; Ritter, T. Tetrahedron 2011, 67, 4449
11. Fier, P.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 5524
12. Litvinas, N. D.; Fier, P. S.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 536
13. Morimoto, H.; Tsubogo, T.; Litvinas, N. D.; Hartwig, J. F. Angew. Chem., Int. Ed. 2011, 50, 3793
14. Grushin, V. V. Acc. Chem. Res. 2010, 43, 160
15. Casitas, A.; Canta, M.; Sola, M.; Costas, M.; Ribas, X. J. Am. Chem. Soc. 2011, 133, 19386
16. Calcd: C, 34.87; H, 4.79; N, 7.39. Found: C, 34.96; H, 4.88; N, 7.53.
17. Paine, A. J. J. Am. Chem. Soc. 1987, 109, 1496
18. Aalten, H. L.; Vankoten, G.; Grove, D. M.; Kuilman, T.; Piekstra, O. G.; Hulshof, L. A.; Sheldon, R. A. Tetrahedron 1989, 45, 5565
19. Couture, C.; Paine, A. J. Can. J. Chem. 1985, 63, 111
20. Arai, S.; Hida, M.; Yamagishi, T. Bull. Chem. Soc. Jpn. 1978, 51, 277
21. Bethell, D.; Jenkins, I. L.; Quan, P. M. J. Chem. Soc., Perkin Trans. 2 1985, 1789
22. Zhang, S. L.; Liu, L.; Fu, Y.; Guo, Q. X. Organometallics 2007, 26, 4546
23. Weingarten, H. J. Org. Chem. 1964, 29, 3624
24. Cohen, T.; Cristea, I. J. Am. Chem. Soc. 1976, 98, 748
25. Abeywickrema, A. N.; Beckwith, A. L. J. J. Chem. Soc., Chem. Comm. 1986, 464
26. Enemaerke, R. J.; Christensen, T. B.; Jensen, H.; Daasbjerg, K. J. Chem. Soc., Perkin Trans. 2 2001, 1620
27. Cohen, T.; Cristea, I. J. Org. Chem. 1975, 40, 3649
28. Cohen, T.; Wood, J.; Dietz, A. G. Tetrahedron Lett. 1974, 3555
29. Grushin, V. V.; Marshall, W. J. Organometallics 2008, 27, 4825
30. Waddington, T. C. Trans. Faraday Soc. 1959, 55, 1531
31. Herron, J. R.; Ball, Z. T. J. Am. Chem. Soc. 2008, 130, 16486
32. Gulliver, D. J.; Levason, W.; Webster, M. Inorg. Chim. Acta 1981, 52, 153