Direct access to α-trifluoromethyl enones via efficient copper-catalyzed trifluoromethylation of meyer-schuster rearrangement

Organic Letters

Volumn 16, Issue 3, 2014, Pages 1000-1003

  Xiong, Ya Ping ^a   Wu, Ming Yue ^a   Zhang, Xiang Yu ^a   Ma, Can Liang ^a   Huang, Lin ^a   Zhao, Li Jiao ^a   Tan, Bin ^a   Liu, Xin Yuan ^a  

^a SOUTHERN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; FLUORINATED HYDROCARBON; HETEROCYCLIC COMPOUND;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYLATION; CATALYSIS; COPPER; HETEROCYCLIC COMPOUNDS; HYDROCARBONS, FLUORINATED; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84893844087     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol403741m     Document Type: Article

References (53)

1. Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
2. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
3. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
4. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475
5. Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455
6. Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470
7. Wu, X.-F.; Neumann, H.; Beller, M. Chem.-Asian J. 2012, 7, 1744
8. Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8950
9. Ye, Y.; Sanford, M. S. Synlett 2012, 23, 2005
10. Liu, H.; Gu, Z.; Jiang, X. Adv. Synth. Catal. 2013, 355, 617
11. Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214
12. Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648
13. Ye, Y.; Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 14682
14. Zhang, X.-G.; Dai, H.-X.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2012, 134, 11948
15. Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224
16. 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
17. Parsons, A. T.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 9120
18. Wang, X.; Ye, Y.; Zhang, S.; Feng, J.; Xu, Y.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 16410
19. Xu, J.; Fu, Y.; Luo, D.-F.; Jiang, Y.-Y.; Xiao, B.; Liu, Z.-J.; Gong, T.-J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 1530
20. Feng, C.; Loh, T.-P. Chem. Sci. 2012, 3, 3458
21. Mizuta, S.; Verhoog, S.; Engle, K. M.; Khotavivattana, T.; O'Duill, M.; Wheelhouse, K.; Rassias, G.; Médebielle, M.; Gouverneur, V. J. Am. Chem. Soc. 2013, 135, 2505
22. Zeng, Y.; Zhang, L.; Zhao, Y.; Ni, C.; Zhao, J.; Hu, J. J. Am. Chem. Soc. 2013, 135, 2955
23. Kong, W.; Casimiro, M.; Merino, E.; Nevado, C. J. Am. Chem. Soc. 2013, 135, 14480
24. Wu, X.; Chu, L.; Qing, F.-L. Angew. Chem., Int. Ed. 2013, 52, 2198
25. Egami, H.; Kawamura, S.; Miyazaki, A.; Sodeoka, M. Angew. Chem., Int. Ed. 2013, 52, 7841
26. Yasu, Y.; Koike, T.; Akita, M. Org. Lett. 2013, 15, 2136
27. Deb, A.; Manna, S.; Modak, A.; Patra, T.; Maity, S.; Maiti, D. Angew. Chem., Int. Ed. 2013, 52, 9747
28. Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2010, 132, 7262
29. Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2012, 134, 1298
30. Chen, Z.-M.; Bai, W.; Wang, S.-H.; Yang, B.-M.; Tu, Y.-Q.; Zhang, F.-M. Angew. Chem., Int. Ed. 2013, 52, 9781
31. Erkkila, A.; Majander, I.; Pihko, P. M. Chem. Rev. 2007, 107, 5416
32. Melchiorre, P. Angew. Chem., Int. Ed. 2012, 51, 9748
33. Rasmusson, G. H.; Brown, R. D.; Arth, G. E. J. Org. Chem. 1975, 40, 672
34. Fei, X.-S.; Tian, W.-S.; Chen, Q.-Y. J. Chem. Soc., Perkin Trans. 1 1998, 1139
35. Chadalapaka, G.; Jutooru, I.; McAlees, A.; Stefanac, T.; Safe, S. Bioorg. Med. Chem. Lett. 2008, 18, 2633
36. Zhang, G.; Peng, Y.; Cui, L.; Zhang, L. Angew. Chem., Int. Ed. 2009, 48, 3112
37. Collins, B. S. L.; Suero, M. G.; Gaunt, M. J. Angew. Chem., Int. Ed. 2013, 52, 5799
38. Lin, J.-S.; Xiong, Y.-P.; Ma, C.-L.; Zhao, L.-J.; Tan, B.; Liu, X.-Y. Chem.-Eur. J. 2014, 20, 1332
39. Li, L.; Deng, M.; Zheng, S.-C.; Xiong, Y.-P.; Tan, B.; Liu, X.-Y. Org. Lett. 2014, 16, 504
40. Eisenberger, P.; Gischig, S.; Togni, A. Chem.-Eur. J. 2006, 12, 2579
41. Kieltsch, I.; Eisenberger, P.; Togni, A. Angew. Chem., Int. Ed. 2007, 46, 754
42. Niedermann, K.; Früh, N.; Vinogradova, E.; Wiehn, M. S.; Moreno, A.; Togni, A. Angew. Chem., Int. Ed. 2011, 50, 1059
43. Narasaka, K.; Kusama, H.; Hayashi, Y. Chem. Lett. 1991, 1413
44. Sun, C.; Lin, X.; Weinreb, S. M. J. Org. Chem. 2006, 71, 3159
45. Engel, D. A.; Dudley, G. B. Org. Biomol. Chem. 2009, 7, 4149
46. Wang, D.; Ye, X.; Shi, X. Org. Lett. 2010, 12, 2088
47. The stereoconfiguration of the products was determined by comparing the NMR spectroscopy of a known compound 2o; see: Bizet, V.; Pannecoucke, X.; Renaud, J. L.; Cahard, D. J. Fluorine Chem. 2013, 152, 56
48. Yu, M.; Zhang, G.; Zhang, L. Org. Lett. 2007, 9, 2147
49. de Haro, T.; Nevado, C. Chem. Commun. 2011, 47, 248
50. Feng, C.; Loh, T.-P. Angew. Chem., Int. Ed. 2013, 52, 12414
51. Zhang, G.; Cui, L.; Wang, Y.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 1474
52. Gandon, V.; Lemiere, G.; Hours, A.; Fensterbank, L.; Malacria, M. Angew. Chem., Int. Ed. 2008, 47, 7534
53. Garayalde, D.; Go mez-Bengoa, E.; Huang, X.; Goeke, A.; Nevado, C. J. Am. Chem. Soc. 2010, 132, 4720