Efficient copper-catalyzed trifluoromethylation of aromatic and heteroaromatic iodides: The beneficial anchoring effect of borates

Organic Letters

Volumn 16, Issue 16, 2014, Pages 4268-4271

  Gonda, Zsombor ^a   Kovács, Szabolcs ^a   Wéber, Csaba ^b   Gáti, Tamás ^b   Mészáros, Attila ^a   Kotschy, András ^b   Novák, Zoltán ^a  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^b Servier Research Institute of Medicinal Chemistry   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

BORIC ACID; COPPER; FLUORINATED HYDROCARBON; IODINATED HYDROCARBON; SILANE DERIVATIVE; TRIMETHYL(TRIFLUOROMETHYL)SILANE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; METHYLATION; SYNTHESIS;

BORATES; CATALYSIS; COPPER; HYDROCARBONS, FLUORINATED; HYDROCARBONS, IODINATED; METHYLATION; MOLECULAR STRUCTURE; SILANES;

EID: 84906249139     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501967c     Document Type: Article

References (54)

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. Barata-Vallejo, S.; Postigo, A. Coord. Chem. Rev. 2013, 257, 3051
9. Chen, P.; Liu, G. Synthesis 2013, 45, 2919
10. Ye, Y.; Sanford, M. S. Synlett 2012, 23, 2005
11. Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513
12. Wu, X.-F.; Neumann, H.; Beller, M. Chem. - Asian J. 2012, 7, 1744
13. Liu, X.; Xu, C.; Wang, M.; Liu, Q. Chem. Rev. 2014, 10.1021/cr400473a
14. Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648
15. Mu, X.; Chen, S.; Zhen, X.; Liu, G. Chem. - Eur. J. 2011, 17, 6039
16. Ye, Y.; Lee, S. H.; Sanford, M. S. Org. Lett. 2011, 13, 5464
17. Jiang, X.; Chu, L.; Qing, F.-L. J. Org. Chem. 2012, 77, 1251
18. Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2012, 134, 1298
19. Senecal, T. D.; Parsons, A. T.; Buchwald, S. L. J. Org. Chem. 2011, 76, 1174
20. Shimizu, R.; Egami, H.; Nagi, T.; Chae, J.; Hamashima, Y.; Sodeoka, M. Tetrahedron Lett. 2010, 51, 5947
21. Xu, J.; Luo, D.-F.; Xiao, B.; Liu, Z.-J.; Gong, T.-J.; Fu, Y.; Liu, L. Chem. Commun. 2011, 47, 4300
22. Liu, T.; Shen, Q. Org. Lett. 2011, 13, 2342
23. Liu, T.; Shao, X.; Wu, Y.; Shen, Q. Angew. Chem., Int. Ed. 2012, 51, 540
24. Sawada, H.; Nakayama, M. J. Fluorine Chem. 1990, 46, 423
25. McClinton, M. A.; McClington, D. A. Tetrahedron 1992, 48, 6555
26. Ji, Y.; Brueckl, T.; Baxter, R. D.; Fujiwara, Y.; Seiple, I. B.; Su, S.; Blackmond, D. G.; Baran, P. S. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 14411
27. Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8950
28. Zheng, Y.; Ma, J.-A. Adv. Synth. Catal. 2010, 352, 2745
29. Merino, E.; Nevado, C. Chem. Soc. Rev. 2014, 10.1039/c4cs00025k
30. Samant, B. S.; Kabalka, G. W. Chem. Commun. 2011, 47, 7236
31. Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679
32. Dubinina, G. G.; Furutachi, H.; Vicic, D. A. J. Am. Chem. Soc. 2008, 130, 8600
33. Dubinina, G. G.; Ogikubo, J.; Vicic, D. A. Organometallics 2008, 27, 6233
34. 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
35. Morimoto, H.; Tsubogo, T.; Litvinas, N. D.; Hartwig, J. F. Angew. Chem., Int. Ed. 2011, 50, 3793
36. Tomashenko, O. A.; Escudero, E. C.; Belmonte, M. M.; Grushin, V. V. Angew. Chem., Int. Ed. 2011, 50, 7655
37. Liu, T.; Shen, Q. Eur. J. Org. Chem. 2012, 2012, 6679
38. Kremlev, M. M.; Mushta, A. I.; Tyrra, W.; Yagupolskii, Y. L.; Naumann, D.; Moeller, A. J. Fluorine Chem. 2012, 133, 67
39. Chen, M.; Buchwald, S. L. Angew. Chem., Int. Ed. 2013, 52, 11628
40. Mulder, J. A.; Frutos, R. P.; Patel, N. D.; Qu, B.; Sun, X.; Tampone, T. G.; Gao, J.; Sarvestni, M.; Eriksson, M. C.; Haddad, N.; Shen, S.; Song, J. J.; Senanayake, C. H. Org. Process Res. Dev. 2013, 17, 940
41. Zanardi, A.; Novikov, M. A.; Martin, E.; Benet-Buchholz, J.; Grushin, V. V. J. Am. Chem. Soc. 2011, 133, 20901
42. Serizawa, H.; Aikawa, K.; Mikami, K. Chem. - Eur. J. 2013, 19, 17692
43. Kobayashi, Y.; Kumadaki, I. Tetrahedron Lett. 1969, 10, 4095
44. Urata, H.; Fuchikami, T. Tetrahedron Lett. 1991, 32, 91
45. Lishchynskyi, A.; Novikov, M. A.; Martin, E.; Escuedo-Adán, E. C.; Novák, P.; Grushin, V. V. J. Org. Chem. 2013, 78, 11126
46. Oishi, M.; Kondo, H.; Amii, H. Chem. Commun. 2009, 1909
47. Knauber, T.; Arikan, F.; Roeschenthaler, G.-V.; Goossen, L. J. Chem. - Eur. J. 2011, 17, 2689
48. Kondo, H.; Oishi, M.; Fujikawa, K.; Amii, H. Adv. Synth. Catal. 2011, 353, 1247
49. Weng, Z.; Lee, R.; Jia, W.; Yuan, Y.; Wang, W.; Feng, X.; Huang, K.-W. Organometallics 2011, 30, 3229
50. Li, Y.; Chen, T.; Wang, H.; Zhang, R.; Jin, K.; Wang, X.; Duan, C. Synlett 2011, 12, 1713
51. Popov, I.; Lindeman, S.; Daugulis, O. J. Am. Chem. Soc. 2011, 133, 9286
52. Schareina, T.; Wu, X.-F.; Zapf, A.; Cotté, A.; Gotta, M.; Beller, M. Top. Catal. 2012, 55, 426
53. Nakamura, Y.; Fujiu, M.; Murase, T.; Itoh, Y.; Serizawa, H.; Aikawa, K.; Mikami, K. Beilstein J. Org. Chem. 2013, 9, 2404
54. Prakash, G. K. S.; Jog, P. V.; Batamack, P. T. D.; Olah, G. A. Science 2012, 338, 1324