Silver-mediated trifluoromethylation of arenes using TMSCF 3

Organic Letters

Volumn 13, Issue 20, 2011, Pages 5464-5467

  Ye, Yingda ^a   Lee, Shin Hee ^a   Sanford, Melanie S ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; FLUORINATED HYDROCARBON; MESYLIC ACID DERIVATIVE; PALLADIUM; SILANE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; TRIMETHYL(TRIFLUOROMETHYL)SILANE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

BENZENE DERIVATIVES; CATALYSIS; HYDROCARBONS, FLUORINATED; MESYLATES; MOLECULAR STRUCTURE; PALLADIUM; SILANES;

EID: 80054701792     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202174a     Document Type: Article

References (47)

1. Schlosser, M. Angew. Chem., Int. Ed. 2006, 45, 5432
2. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
3. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359
4. Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305
5. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
6. Grushin, V. V.; Tomashenko, O. A. Chem. Rev. 2011, 111, 4475
7. Roy, S.; Gregg, B. T.; Gribble, G. W.; Le, V.-D.; Roy, S. Tetrahedron 2011, 67, 2161
8. Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2006, 128, 4632
9. Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2006, 128, 12644
10. Grushin, V. V. Acc. Chem. Res. 2010, 43, 160
11. Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 2878
12. Ye, Y.; Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 14682
13. Ball, N. D.; Gary, J. B.; Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 7577
14. Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648
15. Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679
16. Mu, X.; Chen, S.; Zhen, X.; Liu, G. Chem.-Eur. J. 2011, 17, 6039
17. Loy, R. N.; Sanford, M. S. Org. Lett. 2011, 13, 2548
18. Dubinina, G. G.; Furutachi, H.; Vicic, D. A. J. Am. Chem. Soc. 2008, 130, 8600
19. Dubinina, G. G.; Ogikubo, J.; Vicic, D. A. Organometallics 2008, 27, 6233
20. Chu, L.; Qing, F.-L. Org. Lett. 2010, 12, 5060
21. McReynolds, K. A.; Lewis, R. S.; Ackerman, L. K. G.; Dubinina, G. G.; Brennessel, W. W.; Vicic, D. A. J. Fluorine Chem. 2010, 131, 1108
22. Senecal, T. D.; Parsons, A. T.; Buchwald, S. L. J. Org. Chem. 2011, 76, 1174
23. Zhang, C.-P.; Wang, Z.-L.; Chen, Q.-Y.; Zhang, C.-T.; Gu, Y.-C.; Xiao, J.-C. Angew. Chem., Int. Ed. 2011, 50, 1896
24. Morimoto, H.; Tsubogo, T.; Litvinas, N. D.; Hartwig, J. F. Angew. Chem., Int. Ed. 2011, 50, 3793
25. Tomashenko, O. A.; Escudero, E. C.; Belmonte, M. M.; Grushin, V. V. Angew. Chem., Int. Ed. 2011, 50, 7655
26. Oishi, M.; Konda, H.; Amii, H. Chem. Commun. 2009, 1909
27. Shimizu, R.; Egami, H.; Nagi, T.; Chae, J.; Hamashima, Y.; Sodeoka, M. Tetrahedron Lett. 2010, 51, 5947
28. Knauber, T.; Arikan, F.; Röschenthaler, G.-V.; Gooßen, L. J. Chem.-Eur. J. 2011, 17, 2689
29. Xu, J.; Luo, D.-F.; Xiao, B.; Liu, Z.-J.; Gong, T.-J.; Fu, Y.; Liu, L. Chem. Commun. 2011, 47, 4300
30. Liu, T.; Shen, Q. Org. Lett. 2011, 13, 2342
31. Wakselman, C.; Tordeux, M. J. Chem. Soc., Chem. Commun. 1987, 1701
32. Akiyama, T.; Kato, K.; Kajitani, M.; Sakaguchi, Y.; Nakamura, J.; Hayashi, H.; Sugimori, A. Bull. Chem. Soc. Jpn. 1988, 61, 3531
33. Sawada, H.; Nakayama, M. J. Fluorine Chem. 1990, 46, 423
34. Kirk, K. L.; Nishida, M.; Fujii, S.; Kimoto, H. J. Fluorine Chem. 1992, 59, 197
35. McClinton, M. A.; McClington, D. A. Tetrahedron 1992, 48, 6555
36. Kamigata, N.; Ohtsuka, T.; Fukushima, T.; Yoshida, M.; Shimizu, T. J. Chem. Soc., Perkin Trans. 1 1994, 1339
37. Kino, T.; Nagase, Y.; Ohtsuka, Y.; Yamamoto, K.; Uraguchi, D.; Tokuhisa, K.; Yamakawa, T. J. Fluorine Chem. 2010, 131, 98
38. Ji, Y.; Brueckl, T.; Baxter, R. D.; Fujiwara, Y.; Seiple, I. B.; Su, S.; Blackmond, D. G.; Baran, P. S. Proc. Natl. Acad. Sci. USA 2011, 108, 14411
39. Cowell, A.; Tamborski, C. J. Fluorine Chem. 1981, 17, 345
40. Dolbier, W. R. Chem. Rev. 1996, 96, 1557
41. Bravo, A.; Bjørsvik, H.-R.; Fontana, F.; Liguori, L.; Mele, A.; Minisci, F. J. Org. Chem. 1997, 62, 7128
42. Huang, X.-T.; Long, Z.-Y.; Chen, Q.-Y. J. Fluorine Chem. 2001, 111, 107
43. Li, Y.; Li, C.; Yue, W.; Jiang, W.; Kopecek, R.; Qu, J.; Wang, Z. Org. Lett. 2010, 12, 2374
44. Teverovskiy, G.; Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 7312
45. Huang, C.; Liang, T.; Harada, S.; Lee, E.; Ritter, T. J. Am. Chem. Soc. 2011, 133, 13308
46. For a review on silver perfluoroalkyl complexes: Tyrra, W. E.; Naumann, D. J. Fluorine Chem. 2004, 125, 823
47. Wang, Z.; Lee, R.; Jia, W.; Yuan, Y.; Wang, W.; Feng, X.; Huang, K. W. Organometallics 2011, 30, 3229