Copper-catalyzed trifluoromethylation of aryl and vinyl boronic acids with an electrophilic trifluoromethylating reagent

Organic Letters

Volumn 13, Issue 9, 2011, Pages 2342-2345

  Liu, Tianfei ^a   Shen, Qilong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; COPPER; FLUORINE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; METHYLATION;

BORONIC ACIDS; CATALYSIS; COPPER; FLUORINE COMPOUNDS; METHYLATION; MOLECULAR STRUCTURE; VINYL COMPOUNDS;

EID: 79955631195     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2005903     Document Type: Article

References (47)

1. McClinton, M. A. Tetrahedron 1992, 48, 6555
2. Ma, J. A.; Cahard, D. Chem. Rev. 2008, 108, PR1
3. Clark, J. H.; Wails, D.; Bastock, T. W. Aromatic Fluorination; CRC Press: Boca Raton, FL, 1996.
4. Bégué, J. P.; Bonnet-Delpon, D. Bioorganic and Medicinal Chemistry of Fluorine; Wiley-Interscience: Hoboken, NJ, 2008.
5. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
6. Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305
7. Roy, S.; Gregg, B. T.; Gribble, G. W.; Le, V.; Roy, S. Tetrahedron 2011, 67, 2161
8. Swarts, F. Bull. Acad. R. Belg. 1892, 24, 309
9. Simons, J. H.; Lewis, C. J. J. Am. Chem. Soc. 1938, 60, 492
10. Henne, A. L.; Newman, M. S. J. Am. Chem. Soc., 1938, 60, 1697
11. Riera, J.; Castafier, J.; Carilla, J.; Robert, A. Tetrahedron Lett. 1989, 30, 3825
12. Castafler, J.; Riera, J.; Carilla, J.; Robert, A.; Molins, E.; Miravitlles, C. J. Org. Chem. 1991, 56, 103
13. Kobayashi, Y.; Kumadaki, I. Tetrahedron Lett. 1969, 47, 4095
14. McLaughlin, V. C. R.; Thrower, J. Tetrahedron 1969, 25, 5921
15. Wiemers, D. M.; Burton, D. J. J. Am. Chem. Soc. 1986, 108, 832
16. Carr, G. E.; Chambers, R. D.; Holmes, T. F.; Parker, D. G. J. Chem. Soc., Perkin Trans. I 1988, 921
17. Suzuki, H.; Yoshida, Y.; Osuka, A. Chem. Lett. 1982, 135
18. Urata, H.; Fuchikami, T. Tetrahedron Lett. 1991, 32, 91
19. Chen, Q.-Y.; Wu, S.-W. Chem. Commun. 1989, 705
20. Su, D.-B.; Duan, J.-X.; Chen, Q.-Y. Tetrahedron Lett. 1991, 32, 7689
21. Chen, Q.-Y.; Duan, J.-X. Chem. Commun. 1993, 1389
22. Dubinina, G. G.; Furutachi, H.; Vicic, D. A. J. Am. Chem. Soc. 2008, 130, 8600
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. doi: 10.1002/anie.201100633.
25. Oishi, M.; Kondo, H.; Amii, H. Chem. Commun. 2009, 1909
26. Lundgren, R. J.; Stradiotto, M. Angew. Chem., Int. Ed. 2010, 49, 9322
27. Knauber, T.; Arikan, F.; G., R.; Goossen, L. J. Chem.-Eur. J. 2011, 17, 2689
28. Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679
29. Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2006, 128, 4632
30. Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2006, 128, 12644
31. Chu, L.; Qing, F.-L. Org. Lett. 2010, 12, 5060
32. Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2010, 132, 7262
33. Senecal, T. D.; Parsons, A. T.; Buchwald, S. L. J. Org. Chem. 2011, 76, 1174
34. Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 2878
35. Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648
36. For selected metal-mediated functionalization of arylboronic acids, see: Anbarasan, P.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2011, 50, 519
37. Liskey, C. W.; Liao, X.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 11389
38. Murphy, J. M.; Liao, X.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 15434
39. Kang, S.; Lee, H.; Jang, S.; Ho, P. J. Org. Chem. 1996, 61, 4720
40. Kang, S.; Yamaguchi, T.; Kim, T.; Ho, P. J. Org. Chem. 1996, 61, 9082
41. Kang, S.; Lee, H.; King, J.; Choi, S. Tetrahedron Lett. 1996, 37, 3723
42. For recent reviews on applications of hypervalent iodine see: Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 109, 5299
43. Brand, J. P.; González, D. F.; Nicolai, S.; Waser, J. Chem. Commun. 2011, 47, 102
44. Eisenberger, P.; Gischig, S.; Togni, A. Chem.-Eur. J. 2006, 12, 2579
45. Niedermann, K.; Früh, N.; Vinogradova, E.; Wiehn, M. S.; Moreno, A.; Togni, A. Angew. Chem., Int. Ed. 2011, 50, 1059
46. Koller, R.; Stanek, K.; Stolz, D.; Aardoom, R.; Niedermann, K.; Togni, A. Angew. Chem. 2009, 121, 4396
47. After our submission, Liu et al. reported a Cu-catalyzed method for trifluoromethylation with Umemoto's reagent: Xu, J.; Luo, D.-F.; Xiao, B.; Liu, J.; Gong, T.-J.; Fu, Y.; Liu, L. Chem. Commun. 2011, 47, 4300.