Efficient copper-catalyzed direct intramolecular aminotrifluoromethylation of unactivated alkenes with diverse nitrogen-based nucleophiles

Chemistry - A European Journal

Volumn 20, Issue 5, 2014, Pages 1332-1340

  Lin, Jin Shun ^a   Xiong, Ya Ping ^a   Ma, Can Liang ^a   Zhao, Li Jiao ^a   Tan, Bin ^a   Liu, Xin Yuan ^a  

^a SOUTHERN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Alkenes; Aminotrifluoromethylation; Copper; Nitrogen heterocycles; Nitrogen based nucleophiles

Indexed keywords

COPPER; HYDROCARBONS; NUCLEOPHILES; OLEFINS; SULFUR COMPOUNDS; UREA;

AMINOTRIFLUOROMETHYLATION; AROMATIC AMINES; COPPER SALT; DIFUNCTIONALIZATION; MECHANISTIC STUDIES; NITROGEN HETEROCYCLES; PLAUSIBLE MECHANISMS; PYRROLIDINES;

NITROGEN;

ALKENE; COPPER; INDOLE DERIVATIVE; INDOLINE; NITROGEN; PYRROLIDINE DERIVATIVE; SULFONAMIDE;

AMINOTRIFLUOROMETHYLATION; ARTICLE; CATALYSIS; CHEMISTRY; METHYLATION; NITROGEN HETEROCYCLES; NITROGEN-BASED NUCLEOPHILES;

ALKENES; AMINOTRIFLUOROMETHYLATION; COPPER; NITROGEN HETEROCYCLES; NITROGEN-BASED NUCLEOPHILES;

ALKENES; CATALYSIS; COPPER; INDOLES; METHYLATION; NITROGEN; PYRROLIDINES; SULFONAMIDES;

EID: 84893870843     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201303387     Document Type: Article

References (90)

1. For selected recent examples, see: a) D. L. Boger, C. W. Boyce, R. M. Garbaccio, J. A. Goldberg, Chem. Rev. 1997, 97, 787-828
2. S. M. Weinreb Chem. Rev. 2006,106, 2531-2549.
3. Organofluorine Chemistry: Principles and Commercial Applications (Eds.: R. E. Banks, B. E. Smart, J. C. Tatlow), Plenum, New York, 1994.
4. For selected reviews on trifluoromethylation and fluorination of organic compounds, see: a) S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320-330
5. O. A. Tomashenko V. V. Grushin, Chem. Rev. 2011, 111, 4475-2521
6. Y. Ye, M. S. Sanford, Synlett 2012, 23, 2005-2013
7. T. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470-477
8. X.-F. Wu, H. Neumann, M. Beller, Chem. Asian J. 2012, 7, 1744-1754
9. A. Studer, Angew. Chem. 2012, 124, 9082-9090;
10. Angew. Chem. Int. Ed. 2012, 51, 8950-8958
11. J. Nie, H.-C. Guo, D. Cahard, J.-A. Ma, Chem. Rev. 2011, 111, 455-529.
12. For Cu-catalyzed trifluoromethylation of unactivated alkenes, see: a) A. T. Parsons, S. L. Buchwald, Angew. Chem. 2011, 123, 9286-9289;
13. Angew. Chem. Int. Ed. 2011, 50, 9120-9123
14. J. Xu Y. Fu D.-F. Luo Y.-Y. Jiang B. Xiao Z.-J. Liu T.-J. Gong L. Liu J. Am. Chem. Soc. 2011, 133, 15300-15303
15. X. Wang, Y. Ye, S. Zhang, J. Feng, Y. Xu, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2011, 133, 16410-16413.
16. For selected examples of trifluoromethylation with Togni's reagent, see: a) P. Eisenberger, S. Gischig, A. Togni, Chem. Eur. J. 2006, 12, 2579-2586
17. I. Kieltsch P. Eisenberger A. Togni Angew. Chem. 2007, 119, 768-771;
18. Angew. Chem. Int. Ed. 2007, 46, 754-757
19. R. Koller, K. Stanek, D. Stolz, R. Aardoom, K. Niedermann, A. Togni, Angew. Chem. 2009, 121, 4396-4400;
20. Angew. Chem. Int. Ed. 2009, 48, 4332-4336;
21. M. S. Wiehn, E. V. Vinogradova, A. Togni, J. Fluorine Chem. 2010, 131, 951-957
22. K. Niedermann, N. Frh, E. Vinogradova, M. S. Wiehn, A. Moreno, A. Togni, Angew. Chem. 2011, 123, 1091-1095;
23. Angew. Chem. Int. Ed. 2011, 50, 1059-1063
24. A. E. Allen, D. W. C. MacMillan, J. Am. Chem. Soc. 2010, 132, 4986-4987
25. Q.-H. Deng, H. Wadepohl, L. H. Gade, J. Am. Chem. Soc. 2012, 134, 10769-10772.
26. For selected reports on trifluoromethylation with electrophilic trifluoromethylating reagents, see: a) T. Umemoto, S. Ishihara, Tetrahedron Lett. 1990, 31, 3579-3582
27. T. Umemoto S. Ishihara J. Am. Chem. Soc. 1993, 115, 2156-2164
28. T. Umemoto, K. Adachi, J. Org. Chem. 1994, 59, 5692-5699
29. X. Wang, L. Truesdale, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 3648-3649
30. Y. Ye, N. D. Ball, J. W. Kampf, M. S. Sanford, J. Am. Chem. Soc. 2010, 132, 14682-14687
31. A. Matsnev, S. Noritake, Y. Nomura, E. Tokunaga, S. Nakamura, N. Shibata, Angew. Chem. 2010, 122, 582-586;
32. Angew. Chem. Int. Ed. 2010, 49, 572-576
33. Y. Nomura, E. Tokunaga, N. Shibata, Angew. Chem. 2011, 123, 1925-1929;
34. Angew. Chem. Int. Ed. 2011, 50, 1885-1889
35. X.-G. Zhang, H.-X. Dai, M. Wasa, J.-Q. Yu, J. Am. Chem. Soc. 2012, 134, 11948-11951.
36. For selected recent reports on the catalytic trifluoromethylation of alkenes, see: a) C. Feng, T.-P. Loh, Chem. Sci. 2012, 3, 3458-3462
37. L. Chu F.-L. Qing Org. Lett. 2012, 14, 2106-2109
38. S. Mizuta, O. Galicia-Lpez, K. M. Engle, S. Verhoog, K. Wheelhouse, G. Rassias, V. Gouverneur, Chem. Eur. J. 2012, 18, 8583-8587
39. C.-J. Wallentin, J. D. Nguyen, P. Finkbeiner, C. R. J. Stephenson, J. Am. Chem. Soc. 2012, 134, 8875-8884
40. N. Iqbal, S. Choi, E, Kim, E. J. Cho, J. Org. Chem. 2012, 77, 11383-11387
41. R. Shimizu, H. Egami, Y. Hamashima, M. Sodeoka, Angew. Chem. 2012, 124, 4655-4658;
42. Angew. Chem. Int. Ed. 2012, 51, 4577-4580
43. X. Wu, L. Chu, F.-L. Qing, Angew. Chem. 2013, 125, 2254-2258;
44. Angew. Chem. Int. Ed. 2013, 52, 2198-2202
45. S. Mizuta, S. Verhoog, K. M. Engle, T. Khotavivattana, M. O'Duill, K. Wheelhouse, G. Rassias, M. Mdebielle, V. Gouverneur, J. Am. Chem. Soc. 2013, 135, 2505-2508
46. S. Mizuta, K. M. Engle, S. Verhoog, O. Galicia-Lpez, M. O'Duill, M. Mdebielle, K. Wheelhouse, G. Rassias, A. L. Thompson, V. Gouverneur, Org. Lett. 2013, 15, 1250-1253.
47. For selected recent examples of oxytrifluoromethylation reactions of C= C bonds, see: a) T. Fuchikami, Y. Shibata, H. Urata, Chem. Lett. 1987, 16, 521-524
48. K. Uneyama, Tetrahedron 1991, 47, 555-562
49. Y. Sato, S. Watanabe, K. Uneyama, Bull. Chem. Soc. Jpn. 1993, 66, 1840-1843
50. T. Yajima, H. Nagano, C. Saito, Tetrahedron Lett. 2003, 44, 7027-7029;
51. C.-P. Zhang, Z.-L. Wang, Q.-Y. Chen, C.-T. Zhang, Y.-C. Gu, J.-C. Xiao, Chem. Commun. 2011, 47, 6632-6634
52. H. Egami, R. Shimizu, M. Sodeoka, Tetrahedron Lett. 2012, 53, 5503-5506
53. Y. Li, A. Studer, Angew. Chem. 2012, 124, 8345-8348;
54. Angew. Chem. Int. Ed. 2012, 51, 8221-8224
55. Y. Yasu, T. Koike, M. Akita, Angew. Chem. 2012, 124, 9705-9709;
56. Angew. Chem. Int. Ed. 2012, 51, 9567-9571.
57. R. Zhu, S. L. Buchwald, J. Am. Chem. Soc. 2012, 134, 12462-12465;
58. P. G. Janson, I. Ghoneim, N. O. Ilchenko, K. J. Szab, Org. Lett. 2012, 14, 2882-2885
59. Y.-T. He, L.-H. Li, Y.-F. Yang, Y.-Q. Wang, J.-Y. Luo, X.-Y. Liu, Y.-M. Liang, Chem. Commun. 2013, 49, 5687-5689.
60. For selected recent examples of carbotrifluoromethylation reactions of C=C bonds, see: a) X. Mu, T. Wu, H.-Y. Wang, Y.-L. Guo, G. Liu, J. Am. Chem. Soc. 2012, 134, 878-881
61. H. Egami R. Shimizu S. Kawamura M. Sodeoka Angew. Chem. 2013, 125, 4092-4095;
62. Angew. Chem. Int. Ed. 2013, 52, 4000-4003
63. H. Egami, R. Shimizu, M. Sodeoka, J. Fluorine Chem. 2013, 152, 51-55
64. X. Liu, F. Xiong, X. Huang, L. Xu, P. Li, X. Wu, Angew. Chem. 2013, 125, 7100-7104;
65. Angew. Chem. Int. Ed. 2013, 52, 6962-6966.
66. H. Egami, S. Kawamura, A. Miyazaki, M. Sodeoka, Angew. Chem. 2013, 125, 7995-7998;
67. Angew. Chem. Int. Ed. 2013, 52, 7841-7844;
68. E. Kim S. Choi H. Kim E. J. Cho Chem. Eur. J. 2013, 19, 6209-6212;
69. Y. Yasu, T. Koike, M. Akita, Org. Lett. 2013, 15, 2136-2139.
70. T. Wirth, Angew. Chem. 2005, 117, 3722-3731;
71. Angew. Chem. Int. Ed. 2005, 44, 3656-3665
72. V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523-2584;
73. V. V. Zhdankin, P. J. Stang, Chem. Rev. 2008, 108, 5299-5358.
74. T. E. Mller, K. C. Hultzsch, M. Yus, F. Foubelo, M. Tada, Chem. Rev. 2008, 108, 3795.
75. X.-Y. Liu, C.-H. Li, C.-M. Che, Org. Lett. 2006, 8, 2707-2710
76. X.-Y. Liu, P. Ding, J.-S. Huang, C.-M. Che, Org. Lett. 2007, 9, 2645-2648
77. X.-Y. Liu, C.-M. Che, Angew. Chem. 2008, 120, 3865-3870;
78. Angew. Chem. Int. Ed. 2008, 47, 3805-3810
79. X.-Y. Liu, C.-M. Che, Angew. Chem. 2009, 121, 2403-2407;
80. Angew. Chem. Int. Ed. 2009, 48, 2367-2371
81. X.-Y. Liu, C.-M. Che, Org. Lett. 2009, 11, 4204-4207
82. X.-Y. Liu, Z. Guo, S. S. Dong, X.-H. Li, C.-M. Che, Chem. Eur. J. 2011, 17, 12932-12945
83. X.-Y. Liu, Y.-P. Xiao, F.-M. Siu, L.-C. Ni, Y. Chen, L. Wang, C.-M. Che, Org. Biomol. Chem. 2012, 10, 7208-7219.
84. T. P. Zabawa, S. R. Chemler, Org. Lett. 2007, 9, 2035-2038.
85. T. P. Zabawa, D. Kasi, S. R. Chemler, J. Am. Chem. Soc. 2005, 127, 11250-11251
86. K. Komeyama T. Morimoto K. Takaki Angew. Chem. 2006, 118, 3004-3007;
87. Angew. Chem. Int. Ed. 2006, 45, 2938-2941.
88. E. S. Sherman, P. H. Fuller, D. Kasi, S. R. Chemler, J. Org. Chem. 2007, 72, 3896-3905
89. M. T. Bovino, S. R. Chemler, Angew. Chem. 2012, 124, 3989-3993;
90. Angew. Chem. Int. Ed. 2012, 51, 3923-3927.