Copper-catalyzed β-trifluoromethylation of conjugated hydrazones

Organic Letters

Volumn 16, Issue 18, 2014, Pages 4770-4773

  Prieto, Alexis ^a   Jeamet, Emeric ^a   Monteiro, Nuno ^a   Bouyssi, Didier ^a   Baudoin, Olivier ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84916208254     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5022228     Document Type: Article

References (46)

1. (a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
2. (b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
3. (c) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
4. For reviews of trifluoromethylation processes, see: (a) Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470.
5. (b) Macé, Y.; Magnier, E. Eur. J. Org. Chem. 2012, 2479.
6. (c) Shibata, N.; Matsnev, A.; Cahard, D. Beilstein J. Org. Chem. 2012, 6, 65.
7. (d) Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8950.
8. (e) Landelle, G.; Panossian, A.; Pazenok, S.; Vors, J.-P.; Leroux, F. R. Beilstein J. Org. Chem. 2013, 9, 2476.
9. (f) Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214.
10. (g) Liu, H.; Gu, Z.; Jiang, X. Adv. Synth. Catal. 2013, 355, 617.
11. (a) Konno, T. Trifluoromethyl (CF3) group insertion methods in stereoselective synthesis. In Stereoselective synthesis of drugs and natural products; Andrushko, V., Andrushko, N., Eds.; Wiley: Weinheim, 2013; pp 769-806.
12. (b) Chelucci, G. Chem. Rev. 2012, 112, 1344.
13. (c) Amii, H.; Uneyama, K. Chem. Rev. 2009, 109, 2119.
14. (a) Xiao, J.; Weisblum, B.; Wipf, P. J. Am. Chem. Soc. 2005, 127, 5742.
15. (b) Kobayashi, K.; Narumi, T.; Oishi, S.; Ohno, H.; Fujii, N. J. Org. Chem. 2009, 74, 4626.
16. Egami, H.; Shimizu, R; Sodeoka, M. Tetrahedron Lett. 2012, 53, 5503.
17. Feng, C; Loh, T.-P. Chem. Sci. 2012, 3, 3458.
18. For other reports on direct trifluoromethylation of unfunctionalized alkenes, see: (a) Iqbal, N.; Choi, S.; Kim, E.; Cho, E. J. J. Org. Chem. 2012, 77, 11383.
19. (b) Wang, X.-P.; Lin, J.-H.; Zhang, C.-P.; Xiao, J.-C; Zheng, X. Beilstein J. Org. Chem. 2013, 9, 2635.
20. (c) Tomita, R; Yasu, Y.; Koike, T.; Akita, M. Beilstein J. Org. Chem. 2014, 10, 1099.
21. Fang, Z.; Ning, Y.; Mi, P.; Liao, P.; Bi, X. Org. Lett. 2014, 16, 1522.
22. For other reports dealing with α-trifluoromethylation of conjugated carbonyl compounds, which includes heterocyclic compounds, see: (a) Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224.
23. (b) Wang, X.; Ye, Y.; Ji, G.; Xu, Y.; Zhang, S.; Feng, J.; Zhang, Y.; Wang, J. Org. Lett. 2013, 15, 3730.
24. (c) Ilchenko, N. O.; Janson, P. G.; Szabó, K. J. Chem. Commun. 2013, 49, 6614.
25. (d) Cao, X.-H.; Pan, X.; Zhou, P.-J.; Zou, J.-P.; Asekun, O. T. Chem. Commun. 2014, 50, 3359.
26. (e) Mao, Z.; Huang, F.; Yu, H.; Chen, J.; Yu, Z.; Xu, Z. Chem.-Eur. J. 2014, 20, 3439.
27. Feng, C; Loh, T.-P. Angew. Chem., Int. Ed. 2013, 52, 12414.
28. Besset, T.; Cahard, D.; Pannecoucke, X. J. Org. Chem. 2014, 79, 423.
29. Pair, E.; Monteiro, N.; Bouyssi, D.; Baudoin, O. Angew. Chem., Int. Ed. 2013, 52, 5346.
30. (a) Lazny, R; Nodzewska, A. Chem. Rev. 2010, 110, 1386.
31. (b) Brehme, R; Enders, D.; Fernandez, R; Lassaletta, J. M. Eur. J. Org. Chem. 2007, 5629.
32. It is of note that addition of fluoroalkyl radicals to α, β-unsaturated hydrazones has been recently reported to give β-addition products exclusively. The reaction employed fluoroalkyl halides as radical precursors in the presence of triethylborane as a radical initiator. However, such conditions do not allow the double bond to be restored, and saturated compounds are thus obtained: (a) Ueda, M.; Iwasada, E.; Miyabe, H.; Miyata, O.; Naito, T. Synthesis 2010, 1999.
33. For reviews of radical additions to hydrazones, see: (b) Miyabe, H.; Yoshioda, E.; Kohtani, S. Curr. Org. Chem. 2010, 14, 1254.
34. (c) Friestad, G. K. Eur. J. Org. Chem. 2005, 3157.
35. (d) Friestad, G. K. Tetrahedron 2001, 57, 5461.
36. (e) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
37. Other possible reaction pathways may be invoked to account for this allylic trifluoromethylation; see: (a) Parsons, A. T.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 9102.
38. (b) Wang, X.; Ye, Y.; Zhang, S.; Feng, J.; Xu, Y.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 16410. See also
39. (c) 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, 15300.
40. For a review of difunctionalization-type trifluoromethylation of alkenes, see: (a) Merino, E.; Nevado, C. Chem. Soc. Rev. 2014, 43, 6598.
41. (b) Egami, H.; Sodeoka, M. Angew. Chem., Int. Ed. 2014, 53, 8294. For alkene oxytrifluoromethylation reactions involving Togni reagent, see refs 5-6 and
42. (c) Janson, P. G.; Ghoneim, I.; Ilchenko, N. O.; Szabó, K. J. Org. Lett. 2012, 14, 2882.
43. (d) Li, Y.; Studer, A. Angew. Chem., Int. Ed. 2012, 53, 1067.
44. (e) Lu, D.-F.; Zhu, C.-L.; Xu, H. Chem. Sci. 2013, 4, 2478.
45. (f) Ilchenko, N. O.; Janson, P. G.; Szabó, K. J. J. Org. Chem. 2013, 78, 11087. See also
46. (g) Gao, P.; Yan, X.-B.; Tao, T.; Yang, F.; He, T.; Song, X.-R; Liu, X.-Y.; Liang, Y.-M. Chem.-Eur. J. 2013, 19, 14420.