Rhenium-catalyzed trifluoromethylation of arenes and heteroarenes by hypervalent iodine reagents

ACS Catalysis

Volumn 2, Issue 4, 2012, Pages 521-527

  Mejía, Esteban ^a   Togni, Antonio ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

catalytic trifluoromethylation; electrophilic trifluoromethylation; hypervalent iodine; methyltrioxorhenium; radical reactions

Indexed keywords

CHLOROFORM SOLVENTS; DEUTERIUM ISOTOPE EFFECT; HETEROARENES; HETEROAROMATIC COMPOUNDS; HYPERVALENT IODINE; HYPERVALENT IODINE REAGENTS; INDUCTION PERIODS; METHYLTRIOXORHENIUM; RADICAL REACTIONS; RADICAL SPECIES; REGIOISOMERS; TRIFLUOROMETHYL; TRIFLUOROMETHYLATION;

AROMATIC COMPOUNDS; BENZENE; DEUTERIUM; IODINE; IODINE COMPOUNDS; ORGANIC SOLVENTS; REACTION KINETICS; RHENIUM;

RHENIUM COMPOUNDS;

EID: 84859611613     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs300089y     Document Type: Article

References (56)

1. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886
2. Kirsch, P. Modern Fluoroorganic Chemistry, Wiley-VCH: Weinheim, 2004.
3. Ma, J.-A.; Cahard, D. J. Fluorine Chem. 2007, 128, 975-996
4. McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555-6666
5. Umemoto, T. Chem. Rev. 1996, 96, 1757-1778
6. Shibata, N.; Matsnev, A.; Cahard, D. Beilstein J. Org. Chem. 2010, 6, doi: 10.3762/bjoc.6.65
7. Naumann, D.; Wilkes, B.; Kischkewitz, J. R. J. Fluorine Chem. 1985, 30, 73-87
8. Umemoto, T.; Ando, A. Bull. Chem. Soc. Jpn. 1986, 59, 447-452
9. Sawada, H.; Nakayama, M.; Yoshida, M.; Yoshida, T.; Kamigata, N. J. Fluorine Chem. 1990, 46, 423-431
10. Patrick, T. B.; Khazaeli, S.; Nadji, S.; Hering-Smith, K.; Reif, D. J. Org. Chem. 1993, 58, 705-708
11. Kino, T.; Nagase, Y.; Ohtsuka, Y.; Yamamoto, K.; Uraguchi, D.; Tokuhisa, K.; Yamakawa, T. J. Fluorine Chem. 2010, 131, 98-105
12. McLoughlin, V. C. R.; Thrower, J. Tetrahedron 1969, 25, 5921-5940
13. Zhang, C.-P.; Wang, Z.-L.; Chen, Q.-Y.; Zhang, C.-T.; Gu, Y.-C.; Xiao, J.-C. Angew. Chem., Int. Ed. 2011, 50, 1896-1900
14. Morimoto, H.; Tsubogo, T.; Litvinas, N. D.; Hartwig, J. F. Angew. Chem., Int. Ed. 2011, 50, 3793-3798
15. Tomashenko, O. A.; Escudero-Adán, E. C.; Martínez Belmonte, M.; Grushin, V. V. Angew. Chem., Int. Ed. 2011, 50, 7655-7659
16. Dubinina, G. G.; Furutachi, H.; Vicic, D. A. J. Am. Chem. Soc. 2008, 130, 8600-8601
17. Knauber, T.; Arikan, F.; Röschenthaler, G.-V.; Goossen, L. J. Chem. - Eur. J. 2011, 17, 2689-2697
18. Senecal, T. D.; Parsons, A. T.; Buchwald, S. L. J. Org. Chem. 2011, 76, 1174-1176
19. Liu, T.; Shen, Q. Org. Lett. 2011, 13, 2342-2345
20. Chu, L.; Qing, F.-L. Org. Lett. 2010, 12, 5060-5063
21. Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679-1681
22. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475-4521
23. Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470-477
24. Eisenberger, P.; Gischig, S.; Togni, A. Chem. - Eur. J. 2006, 12, 2579-2586
25. Kieltsch, I.; Eisenberger, P.; Stanek, K.; Togni, A. Chimia 2008, 62, 260-263
26. Stanek, K.; Koller, R.; Kieltsch, I.; Eisenberger, P.; Togni, A. e-EROS 2009, article Rn01121.
27. Stanek, K.; Koller, R.; Kieltsch, I.; Eisenberger, P.; Togni, A. e-EROS 2009, article Rn01120.
28. Kieltsch, I.; Eisenberger, P.; Togni, A. Angew. Chem., Int. Ed. 2007, 46, 754-757
29. Eisenberger, P.; Kieltsch, I.; Armanino, N.; Togni, A. Chem. Commun. 2008, 1575-1577
30. Stanek, K.; Koller, R.; Togni, A. J. Org. Chem. 2008, 73, 7678-7685
31. Koller, R.; Stanek, K.; Stolz, D.; Aardoom, R.; Niedermann, K.; Togni, A. Angew. Chem., Int. Ed. 2009, 48, 4332-4336
32. Niedermann, K.; Früh, N.; Vinogradova, E. V.; Wiehn, M. S.; Moreno, A.; Togni, A. Angew. Chem. 2011, 123, 1091-1095
33. Wang, X.; Ye, Y.; Zhang, S.; Feng, J.; Xu, Y.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 16410-16413
34. Parsons, A. T.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 9120-9123
35. Allen, A. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 4986-4987
36. Ye, Y.; Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 14682-14687
37. Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648-3649
38. Aisín, C.; Kaufmann, J. S.; Duff, R. J.; Shivaprasad, S.; Beaucage, S. L. Tetrahedron 2010, 66, 68-79
39. Wiehn, M. S.; Vinogradova, E. V.; Togni, A. J. Fluorine Chem. 2010, 131, 951-957
40. Shimizu, R.; Egami, H.; Nagi, T.; Chae, J.; Hamashima, Y.; Sodeoka, M. Tetrahedron Lett. 2010, 51, 5947-5949
41. Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2011, 134, 1298
42. Mu, X.; Chen, S.; Zhen, X.; Liu, G. Chem. - Eur. J. 2011, 17, 6039-6042
43. Litvinas, N. D.; Fier, P. S.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 536-539
44. Liu, T.; Shao, X.; Wu, Y.; Shen, Q. Angew. Chem., Int. Ed. 2012, 51, 540-543
45. Ye, Y.; Lee, S. H.; Sanford, M. S. Org. Lett. 2011, 13, 5464-5467
46. Ji, Y.; Brueckl, T.; Baxter, R. D.; Fujiwara, Y.; Seiple, I. B.; Su, S.; Blackmond, D. G.; Baran, P. S. Proc. Nat. Acad. Sci. 2011, 108, 14411-14415
47. Herrmann, W. A.; Kratzer, R. M.; Fischer, R. W. Angew. Chem., Int. Ed. 1997, 36, 2652-2654
48. Fantasia, S.; Welch, J. M.; Togni, A. J. Org. Chem. 2010, 75, 1779-1782
49. De Meric de Bellefon, C.; Herrmann, W. A.; Kiprof, P.; Whitaker, C. R. Organometallics 1992, 11, 1072-1081
50. Grandberg, I. I.; Faizova, G. K.; Kost, A. N. Chem. Heterocycl. Compd. 1967, 2, 421-425
51. Gero, A.; Markham, J. J. J. Org. Chem. 1951, 16, 1835-1838
52. Kita, Y.; Tohma, H.; Hatanaka, K.; Takada, T.; Fujita, S.; Mitoh, S.; Sakurai, H.; Oka, S. J. Am. Chem. Soc. 1994, 116, 3684-3691
53. Tobisu, M.; Kita, Y.; Ano, Y.; Chatani, N. J. Am. Chem. Soc. 2008, 130, 15982-15989
54. Dohi, T.; Ito, M.; Morimoto, K.; Iwata, M.; Kita, Y. Angew. Chem., Int. Ed. 2008, 47, 1301-1304
55. Dohi, T.; Ito, M.; Yamaoka, N.; Morimoto, K.; Fujioka, H.; Kita, Y. Tetrahedron 2009, 65, 10797-10815
56. Sankararaman, S.; Haney, W. A.; Kochi, J. K. J. Am. Chem. Soc. 1987, 109, 7824-7838