A metal-free route to CF3-containing oxindoles by PhI(OAc) 2-mediated trifluoromethylation of N-arylacrylamides with TMSCF 3

European Journal of Organic Chemistry

Volumn 2014, Issue 4, 2014, Pages 709-712

  Fu, Weijun ^a   Xu, Fengjuan ^b   Fu, Yuqin ^a   Xu, Chen ^a   Li, Shihui ^a   Zou, Dapeng ^b  

^a LUOYANG NORMAL UNIVERSITY   (China)

^b ZHENGZHOU UNIVERSITY   (China)

Author keywords

Amides; Fluorine; Heterocycles; Iodine; Synthetic methods

Indexed keywords

EID: 84896711498     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201301512     Document Type: Article

References (78)

1. a) P. Kirsch, Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, Germany, 2004;
2. b) K. Uneyama, Organofluorine Chemistry, Blackwell, Oxford, UK, 2006;
3. c) I. Ojima, Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, Chichester, UK, 2009;
4. d) S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320;
5. e) B. E. Smart, Chem. Rev. 1996, 96, 1555.
6. For recent reviews, see: a) T. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473;
7. O. Tomashenko, V. V. Grushin, Chem. Rev. 2011, 111, 4475;
8. c) X. F. Wu, H. Neumann, M. Beller, Chem. Asian J. 2012, 7, 1744;
9. d) Y. Ye, M. S. Sanford, Synlett 2012, 2005;
10. e) A. Studer, Angew. Chem. 2012 124, 9082;
11. Angew. Chem. Int. Ed. 2012, 51, 8950;
12. f) T. Liu, Q. Shen, Eur. J. Org. Chem. 2012, 6679;
13. g) H. Liu, Z. Gu, X. Jiang, Adv. Synth. Catal. 2013, 355, 617;
14. h) R. J. Lundgren, M. Stradiotto, Angew. Chem. 2010, 122, 9510;
15. Angew. Chem. Int. Ed. 2010, 49, 9322
16. i) S. Roy, B. T. Gregg, G. W. Gribble, V.-D. Le, Tetrahedron 2011, 67, 2161;
17. j) T. Besset, C. Schneider, D. Cahard, Angew. Chem. 2012, 124, 5134;
18. k) Angew. Chem. Int. Ed. 2012 51, 5048.
19. For selected examples, see: a) A. Zanardi, M. A. Novikov, E. Martin, J. Benet-Buchholz, V. V. Grushin, J. Am. Chem. Soc. 2011, 133, 20901;
20. b) M. Oishi, H. Kondo, H. Amii, Chem. Commun. 2009, 1909;
21. c) E. J. Cho, T. D. Senecal, T. Kinzel, Y. Zhang, D. A. Watson, S. L. Buchwald, Science 2010, 328, 1679;
22. d) H. Morimoto, T. Tsubogo, N. D. Litvinas, J. F. Hartwig, Angew. Chem. 2011, 123, 3877;
23. Angew. Chem. Int. Ed. 2011, 50, 3793.
24. For selected examples, see: a) T. D. Senecal, A. T. Parsons, S. L. Buchwald, J. Org. Chem. 2011, 76, 1174;
25. b) T. Liu, Q. Shen, Org. Lett. 2011, 13, 2342;
26. c) J. Xu, D.-F. Luo, B. Xiao, Z.-J. Liu, T.-J. Gong, Y. Fu, L. Liu, Chem. Commun. 2011, 47, 4300;
27. d) C.-P. Zhang, J. Cai, C.-B. Zhou, X.-P. Wang, X. Zheng, Y.-C. Gu, J.-C. Xiao, Chem. Commun. 2011, 47, 9516;
28. e) X. Jiang, L. Chu, F.-L. Qing, J. Org. Chem. 2012, 77, 1251;
29. f) B. A. Khan, A. E. Buba, L. J. Gooßen, Chem. Eur. J. 2012, 18, 1577;
30. g) N. D. Litvinas, P. S. Fier, J. F. Hartwig, Angew. Chem. 2012, 124, 551;
31. Angew. Chem. Int. Ed. 2012, 51, 536;
32. h) T. Liu, X. Shao, Y. Wu, Q. Shen, Angew. Chem. 2012, 124, 555;
33. Angew. Chem. Int. Ed. 2012, 51, 540;
34. i) P. Novák, A. Lishchynskyi V. V. Grushin, Angew. Chem. 2012, 124, 7887;
35. Angew. Chem. Int. Ed. 2012, 51, 7767.
36. a) X. Wang, L. Truesdale, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 3648;
37. b) A. Hafner, S. Bräse, Angew. Chem. 2012, 124, 3773;
38. Angew. Chem. Int. Ed. 2012, 51, 3713.
39. a) L. Chu, F.-L. Qing, J. Am. Chem. Soc. 2010, 132, 7262;
40. b) Z. Weng, H. Li, W. He, L.-F. Yao, J. Tan, J. Chen, Y. Yuan, K.-W. Huang, Tetrahedron 2012, 68, 2527.
41. a) A. T. Parsons, S. L. Buchwald, Angew. Chem. 2011, 123, 9286;
42. Angew. Chem. Int. Ed. 2011, 50, 9120;
43. b) X. Wang, Y. Ye, S. Zhang, J. Feng, Y. Xu, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2011, 133, 16410;
44. c) Y. Miyake, S.-I. Ota, Y. Nishibayashi, Chem. Eur. J. 2012, 18, 13255;
45. d) R. Shimizu, H. Egami, Y. Hamashima, M. Sodeoka, Angew. Chem. 2012, 124, 4655;
46. Angew. Chem. Int. Ed. 2012, 51, 4577;
47. e) R. Zhu, S. L. Buchwald,J. Am. Chem. Soc. 2012, 134, 12462.
48. Y. Li, A. Studer, Angew. Chem. 2012, 124, 8345
49. Angew. Chem.Int. Ed. 2012, 51, 8221.
50. For reviews on oxindoles, see: a) J. E. M. N. Klein, R. J. K.Taylor, Eur. J. Org. Chem. 2011, 6821;
51. b) F. Zhou, Y.-L. Liu, J.Zhou, Adv. Synth. Catal. 2010, 352, 1381;
52. for selected examples,see: c) W.-T. Wei, M.-B. Zhou, J.-H. Fan, W. Liu, R.-J. Song, Y. Liu, M. Hu, P. Xie, J.-H. Li, Angew. Chem. 2013, 125, 3726;
53. Angew. Chem. Int. Ed. 2013, 52, 3638;
54. d) Y.-M. Li, M. Sun, H.-L. Wang, Q.-P. Tian, S.-D. Yang, Angew. Chem. 2013, 125, 4064;
55. Angew. Chem. Int. Ed. 2013, 52, 3972;
56. e) M.-B. Zhou, R.-J. Song, X.-H. Ouyang, Y. Liu, W.-T. Wei, G.-B. Deng, J.-H. Li, Chem. Sci. 2013, 4, 2690;
57. f) J. Xie, P. Xu, H. Li, Q. Xue, H. Jin, Y. Cheng, C. Zhu, Chem. Commun. 2013, 49, 5672;
58. g) K. Matcha, R. Narayan, A. P. Antonchick, Angew. Chem. 2013, 125, 7985;
59. Angew. Chem. Int. Ed. 2013, 52, 7985;
60. h) Y. Meng, L.-N. Guo, H. Wang, X.-H. Duan, Chem. Commun. 2013, 49, 7540;
61. i) X.-H. Wei, Y.-M. Li, A.-X. Zhou, T.-T. Yang, S.-D. Yang, Org. Lett. 2013, 15, 4158;
62. j) W. Fu, F. Xu, Y. Fu, M. Zhu, J. Yu, C. Xu, D. Zou, J. Org. Chem. 2013, 78, 12202.
63. X. Mu, T. Wu, H. Wang, Y. Guo, G. Liu, J. Am. Chem. Soc. 2012, 134, 878.
64. a) H. Egami, R. Shimizu, M. Sodeoka, J. Fluorine Chem. 2013, 152, 51;
65. b) H. Egami, R. Shimizu, S. Kawamura, M. Sodeoka, Angew. Chem. 2013, 125, 4092;
66. Angew. Chem. Int. Ed. 2013, 52, 4000.
67. P. Xu, J. Xie, Q. Xue, C. Pan, Y. Cheng, C. Zhu, Chem. Eur. J. 2013, 19, 14039.
68. W. Kong, M. Casimiro, E. Merino, C. Nevado, J. Am. Chem. Soc. 2013, 135, 14480.
69. a) X. Wu, L. Chu, F.-L. Qing, Tetrahedron Lett. 2013, 54, 249;
70. b) Y. Ji, T. Brueckl, R. D. Baxter, Y. Fujiwara, I. B. Seiple, S. Su, D. G. Blackmond, P. S. Baran, Proc. Natl. Acad. Sci. USA 2011, 108, 14411;
71. c) C. Xu, J. Liu, W. Ming, Y. Liu, J. Liu, M. Wang, Q. Liu, Chem. Eur. J. 2013, 19, 9104.
72. Y.-D. Yang, K. Iwamoto, E. Tokunaga, N. Shibata, Chem. Commun. 2013, 49, 5510.
73. Q. Wang, Xi. Dong, T. Xiao, L. Zhou, Org. Lett. 2013, 15,4846.
74. a) M. Zhu, W. Fu, G. Zou, C. Xun, D. Deng, B. Ji, J. FluorineChem. 2012, 135, 195;
75. b) W. Fu, W. Guo, G. Zou, C. Xu, J. Fluorine Chem. 2012, 140, 88;
76. c) M. Zhu, W. Fu, C. Xu, G. Zou, Z. Wang, B. Ji, Eur. J. Org. Chem. 2012, 4609;
77. d) M. Zhu, Z. Wang, F. Xu, J. Yu, W. Fu, J. Fluorine Chem. 2013, 156, 21.
78. CCDC-963690 (for 2n) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.