Copper-catalyzed nucleophilic trifluoromethylation of propargylic halides

Chemical Communications

Volumn 49, Issue 71, 2013, Pages 7809-7811

  Miyake, Yoshihiro ^a   Ota, Shin Ichi ^a   Shibata, Masashi ^a   Nakajima, Kazunari ^a   Nishibayashi, Yoshiaki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; HALIDE; THIOPHENE;

ARTICLE; CHEMICAL REACTION; METHYLATION; NUCLEOPHILICITY; TRIFLUOROMETHYLATION;

EID: 84881417762     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc44434a     Document Type: Article

References (48)

1. J.-A. Ma, D. Cahard, Chem. Rev., 2008, 108, PR1
2. O. A. Tomashenko, V. V. Grushin, Chem. Rev., 2011, 111, 4475
3. T. Furuya, A. S. Kamlet, T. Ritter, Nature, 2011, 473, 470
4. T. Besset, C. Schneider, D. Cahard, Angew. Chem., Int. Ed., 2012, 51, 5048
5. A. Studer, Angew. Chem., Int. Ed., 2012, 51, 8950
6. K. Müller, C. Faeh, F. Diederich, Science, 2007, 317, 1881
7. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev., 2008, 37, 320
8. G. K. S. Prakash and F. Wang, in Organic Chemistry - Breakthroughs and Perspectives, ed. K. Ding and L.-X. Dai, Wiley-VCH, Weinheim, 2012, ch. 12, pp. 413-476
9. N. Shibata, S. Mizuta, H. Kawai, Tetrahedron: Asymmetry, 2008, 19, 2633
10. D. A. Nagib, M. E. Scott, D. W. C. MacMillan, J. Am. Chem. Soc., 2009, 131, 10875
11. A. E. Allen, D. W. C. MacMillan, J. Am. Chem. Soc., 2010, 132, 4986
12. A. T. Parsons, S. L. Buchwald, Angew. Chem., Int. Ed., 2011, 50, 9120
13. 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
14. X. Wang, Y. Ye, S. Zhang, J. Feng, Y. Xu, Y. Zhang, J. Wang, J. Am. Chem. Soc., 2011, 133, 16410
15. R. Shimizu, H. Egami, Y. Hamashima, M. Sodeoka, Angew. Chem., Int. Ed., 2012, 51, 4577
16. L. Chu, F.-L. Qing, Org. Lett., 2012, 14, 2106
17. P. G. Janson, I. Ghoneim, N. O. IIchenko, K. J. Szabó, Org. Lett., 2012, 14, 2882
18. R. Zhu, S. L. Buchwald, J. Am. Chem. Soc., 2012, 134, 12462
19. Y. Li, A. Studer, Angew. Chem., Int. Ed., 2012, 51, 8221
20. Y. Yasu, T. Koike, M. Akita, Angew. Chem., Int. Ed., 2012, 51, 9567
21. Y. Miyake, S. Ota, Y. Nishibayashi, Chem. Eur. J., 2012, 18, 13255
22. Y. Kobayashi, K. Yamamoto, I. Kumadaki, Tetrahedron Lett., 1979, 20, 4071
23. J.-P. Bouillon, C. Maliverney, R. Merényi, H. G. Viehe, J. Chem. Soc., Perkin Trans. 1, 1991, 2147
24. H. Urata, T. Fuchikami, Tetrahedron Lett., 1991, 32, 91
25. D.-B. Su, J.-X. Duan, Q.-Y. Chen, Tetrahedron Lett., 1991, 32, 7689
26. Q.-Y. Chen, J.-X. Duan, J. Chem. Soc., Chem. Commun., 1993, 1389
27. J. Kim, J. M. Shreeve, Org. Biomol. Chem., 2004, 2, 2728
28. G. W. Kabalka, M. L. Yao, Curr. Org. Synth., 2008, 5, 28
29. N. Ljungdahl, N. Kann, Angew. Chem., Int. Ed., 2009, 48, 642
30. Y. Miyake, S. Uemura, Y. Nishibayashi, ChemCatChem, 2009, 1, 342
31. R. J. Detz, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem., 2009, 6263
32. C.-H. Ding, X.-L. Hou, Chem. Rev., 2011, 111, 1914
33. Y. Nishibayashi, Synthesis, 2012, 489
34. K. Fukamizu, Y. Miyake, Y. Nishibayashi, J. Am. Chem. Soc., 2008, 130, 10498
35. M. Ikeda, Y. Miyake, Y. Nishibayashi, Angew. Chem., Int. Ed., 2010, 49, 7289
36. M. Ikeda, Y. Miyake, Y. Nishibayashi, Chem. Eur. J., 2012, 18, 3321
37. G. Hattori, H. Matsuzawa, Y. Miyake, Y. Nishibayashi, Angew. Chem., Int. Ed., 2008, 47, 3781
38. G. Hattori, K. Sakata, H. Matsuzawa, Y. Tanabe, Y. Miyake, Y. Nishibayashi, J. Am. Chem. Soc., 2010, 132, 10592
39. A. Yoshida, G. Hattori, Y. Miyake, Y. Nishibayashi, Org. Lett., 2011, 13, 2460
40. D. J. Burton, G. A. Hartgraves, J. Hsu, Tetrahedron Lett., 1990, 31, 3699
41. H. Kawai, T. Furukawa, Y. Nomura, E. Tokunaga, N. Shibata, Org. Lett., 2011, 13, 3596
42. T. S. N. Zhao, K. J. Szabó, Org. Lett., 2012, 14, 3966
43. G. K. S. Prakash, A. K. Yudin, Chem. Rev., 1997, 97, 757
44. R. P. Singh, J. M. Shreeve, Tetrahedron, 2000, 56, 7613
45. C. Zhong, Y. Sasaki, H. Ito, M. Sawamura, Chem. Commun., 2009, 5850
46. H. Ohmiya, U. Yokobori, Y. Makida, M. Sawamura, Org. Lett., 2011, 13, 6312
47. M. Yang, N. Yokokawa, H. Ohmiya, M. Sawamura, Org. Lett., 2012, 14, 816
48. Y. Matsuya, D. Ihara, M. Fukuchi, D. Honma, K. Itoh, A. Tabuchi, H. Nemoto, M. Tsuda, Bioorg. Med. Chem., 2012, 20, 2564