Copper-catalyzed trifluoromethylation of enol ether

Chinese Journal of Organic Chemistry

Volumn 34, Issue 5, 2014, Pages 980-984

  Peng, Rui ^a   Yang, Binmiao ^a   Chen, Zhimin ^a   Xu, Li ^a   Wang, Shaohua ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Copper; Enol ether; Fluorine; Trifluoromethyl

Indexed keywords

EID: 84902163867     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: 10.6023/cjoc201403039     Document Type: Article

References (79)

1. Uneyama K. Organofluorine Chemistry, Blackwell, Oxford U.K., 2006.
2. Hird M. Chem. Soc. Rev. 2007, 36, 2070.
3. Kirk K.L. Org. Process Res. Dev. 2008, 12, 305.
4. O'Hagan D. Chem. Soc. Rev. 2008, 37, 308.
5. Ojima I. Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, Chichester U.K., 2009.
6. Filler R., Saha R. Future Med. Chem. 2009, 1, 777.
7. Daniels S., Tohid S.F.M., Velanguparackel W., Westwell A.D. Expert. Opin. Drug Discovery 2010, 5, 291.
8. Acena J.L., Simon-Fuentes A., Fustero S. Curr. Org. Chem. 2010, 14, 928.
9. Wang X., Zhang Y., Wang J. Sci. China Chem. 2012, 42, 1417 (in Chinese).
10. Qing F.L. Chin. J. Org. Chem. 2012, 32, 815 (in Chinese).
11. Lv C.P., Shen Q.L., Liu D. Chin. J. Org. Chem. 2012, 32, 1380 (in Chinese).
12. Pan F., Shi Z. Acta Chim. Sinica 2012, 70, 1679 (in Chinese).
13. Yu H.Z., Su S.Q., Zhang C., Dang Z.M. Chin. J. Org. Chem. 2013, 33, 1628 (in Chinese).
14. Liu T.F., Shen Q L. Eur. J. Org. Chem. 2012, 6679.
15. Wang G.Z., He X.P., Dai J.J., Xu H. J. Chin. J. Org. Chem. 2014, 34, 837 (in Chinese).
16. Swarts F. Bull. Acad. R. Belg. 1892, 24, 309.
17. Boswell G.A.Jr., Ripka W.C., Scribner R.M., Tullock C.W. Org. React. 1974, 21, 1.
18. Dubinina G.G., Brennessel W.W., Miller J.L., Vicic D.A. Organometallics 2008, 27, 3933.
19. Wang X., Truesdale L., Yu J.-Q. J. Am. Chem. Soc. 2010, 132, 3648.
20. Ye Y., Ball N.D., Kampf J.W., Sanford M.S. J. Am. Chem. Soc. 2010, 132, 14682.
21. Ye Y., Lee S.H., Sanford M.S. Org. Lett. 2011, 13, 5464.
22. Parsons A.T., Senecal T.D., Buchwald S.L. Angew. Chem., Int. Ed. 2012, 51, 2947.
23. Herrmann A.T., Smith L.L., Zakarian A. J. Am. Chem. Soc. 2012, 134, 6976.
24. Iqbal N., Choi S., Kim E., Cho E.J. J. Org. Chem. 2012, 77, 11383.
25. Kazuyuki S., Masaaki O., Akira A., Itsumaro K. Org. Lett. 2013, 23, 4359.
26. Zhang S.-L., Liu L., Fu Y., Guo Q.-X. Organometallics 2007, 26, 4546.
27. Dubinina G.G., Furutachi H., Vicic D.A. J. Am. Chem. Soc. 2008, 130, 8600.
28. Oishi M., Kondo H., Amii H. Chem. Commun. 2009, 1909.
29. Morimoto H., Tsubogo T., Litvinas N.D., Hartwig J.F. Angew. Chem., Int. Ed. 2011, 50, 3793.
30. Zanardi A., Novikov M.A., Martin E., Benet-Buchholz J., Grushin V.U. J. Am. Chem. Soc. 2011, 133, 20901.
31. Tomashenko O.A., Escudero-Adan E.C., Belmonte M.M., Grushin V.U. Angew. Chem., Int. Ed. 2011, 50, 7655.
32. Zhang C.P., Wang Z.L., Chen Q.Y., Zhang C.T., Gu Y.C., Xiao J.C. Angew. Chem., Int. Ed. 2011, 50, 1896.
33. Weng Z., Lee R., Jia W., Yuan Y., Wang W., Feng X., Huang K.W. Organometallics 2011, 30, 3229.
34. Kondo H., Oishi M., Fujikawa K., Amii H. Adv. Synth. Catal. 2011, 353, 1247.
35. Knauber T., Arikan F., Roschenthaler G.-V., Goossen L. J. Chem. Eur. J. 2011, 17, 2689.
36. Duan C., Li Y., Chen T., Wang H., Zhang R., Jin K., Wang X. Synlett 2011, 1713.
37. Chen M., Buchwald S.L. Angew. Chem., Int. Ed. 2013, 52, 11628.
38. Hafner A., Braese S. Adv. Synth. Catal. 2011, 353, 3044.
39. Kawai H., Furukawa T., Nomura Y., Tokunaga E., Shibata N. Org. Lett. 2011, 13, 3596.
40. Schareina T., Wu X.-F., Zapf A., Cotté A., Gotta M., Beller M. Top. Catal. 2012, 55, 426.
41. Miyake Y., Ota S., Nishibayashi Y. Chem.-Eur. J. 2012, 18, 13255.
42. Zhao T.S., Szabo K. J. Org. Lett. 2012, 14, 3966.
43. Novak P., Lishchynskyi A., Grushin V.U. J. Am. Chem. Soc. 2012, 134, 16167.
44. Miyake Y., Ota S., Shibata M., Nakajima K., Nishibayashi Y. Chem. Commum. 2013, 49, 7809.
45. Larsson J.M., Pathipati S.R., Szabo K.J. J. Org. Chem. 2013, 78, 7330.
46. Ambler B.R., Altman R.A. Org. Lett. 2013, 15, 5578.
47. Chu L., Qing F.-L. Org. Lett. 2010, 12, 5060.
48. Senecal T.D., Parsons A.T., Buchwald S.L. J. Org. Chem. 2011, 76, 1174.
49. Xu J., Luo D.F., Xiao B., Liu Z.J., Gong T.J., Fu Y., Liu L. Chem. Commun. 2011, 47, 4300.
50. Zhang C.P., Cai J., Zhou C.B., Wang X.P., Zheng X., Gu Y.C., Xiao J.C. Chem. Commun. 2011, 47, 9516.
51. Liu T., Shen Q. Org. Lett. 2011, 13, 2342.
52. Huang Y., Fang X., Lin X., Li H., He W., Huang K.-W., Yuan Y., Weng Z. Tetrahedron 2012, 68, 9949.
53. Ji Y., Brueckl T., Baxter R.D., Fujiwara Y., Seiple I.B., Su S., Blackmond D.G., Baran O.S. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 14411.
54. Ye Y., Künzi S.A., Sanford M.S. Org. Lett. 2012, 14, 4979.
55. Litvinas N.D., Fier O.S., Hartwig J.F. Angew. Chem., Int. Ed. 2012, 51, 536.
56. Liu T., Shao X., Wu Y., Shen Q. Angew. Chem., Int. Ed. 2012, 51, 555.
57. Novák P., Lishchynskyi A., Grushin V.U. Angew. Chem., Int. Ed. 2012, 51, 7767.
58. Khan B.A., Buba A.E., Goossen L. J. Chem.-Eur. J. 2012, 18, 1577.
59. Ye Y., Sanford M.S. J. Am. Chem. Soc. 2012, 134, 9034.
60. Xu J., Xiao B., Xie C.Q., Luo D.F., Liu L., Fu Y. Angew. Chem., Int. Ed. 2012, 51, 12551.
61. Zheng H., Huang Y., Wang Z., Li H., Huang K.-W., Yuan Y., Weng Z. Tetrahedron Lett. 2012, 53, 6646.
62. Li Y., Wu L., Neumann H., Beller M. Chem. Commun. 2013, 49, 2628.
63. Chu L., Qing F.-L. Org. Lett. 2010, 14, 2106.
64. 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.
65. Parsons A.T., Buchwald S.L. Angew. Chem., Int. Ed. 2011, 50, 9120.
66. Wang X., Ye Y., Zhang S., Feng J., Xu Y., Zhang Y., Wang J. J. Am. Chem. Soc. 2011, 133, 16410.
67. Mitsudera H., Li C.-J. Tetrahedron Lett. 2011, 52, 1898.
68. Shimizu R., Egami H., Nagi T., Chae J., Hamashima Y., Sodeoka M. Tetrahedron Lett. 2010, 51, 5947.
69. Chu L., Qing F.L. J. Am. Chem. Soc. 2012, 134, 1298.
70. Pair E., Monteiro N., Bouyssi D., Baudoin O. Angew. Chem., Int. Ed. 2013, 52, 5346.
71. Feng C., Loh T.-P. Chem. Sci. 2012, 3, 3458.
72. Ilchenko N.O., Janson O.G., Szabo K. J. Chem. Commun. 2013, 49, 6614.
73. Wang X., Ye Y., Ji G., Xu Y., Zhang S., Feng J., Zhang Y., Wang J. Org. Lett. 2013, 15, 3730.
74. Chu L., Qing F.-L. J. Am. Chem. Soc. 2010, 132, 7262.
75. Weng Z., Li H., He W., Yao L.-F., Tan J., Chen J., Yuan Y., Huang K.-W. Tetrahedron 2012, 68, 2527.
76. Luo D.-F., Xu J., Fu Y., Guo Q.-X. Tetrahedron Lett. 2012, 53, 2769.
77. Zhang K., Qiu X.-L., Huang Y., Qing F.-L. Eur. J. Org. Chem. 2012, 58.
78. Chen Z.-M., Bai W., Wang S.-H., Yang B.-M., Tu Y.-Q., Zhang F.-M. Angew. Chem., Int. Ed. 2013, 52, 9781.
79. Fang Z., Ning Y., Mi P., Liao P., Bi X., Org. Lett. 2014, 16, 1522.