Recent advances in copper-promoted trifluoromethylation reactions

Chinese Journal of Organic Chemistry

Volumn 34, Issue 5, 2014, Pages 837-851

  Wang, Guangzu ^a   He, Xiaping ^a   Dai, Jianjun ^a   Xu, Huajian ^a,b  

^a HEFEI UNIVERSITY OF TECHNOLOGY   (China)

^b KEY LABORATORY OF ADVANCED FUNCTIONAL MATERIALS AND DEVICES OF ANHUI PROVINCE   (China)

Author keywords

Copper catalyzed; Trifluoromethyl reagents; Trifluoromethylation

Indexed keywords

EID: 84902194041     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: 10.6023/cjoc201311012     Document Type: Review

References (155)

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. Sin. Chim. 2012, 42, 1417.
10. Yu H.Z., Su S.Q., Zhang C., Dang Z.M. Chin. J. Org. Chem. 2013, 33, 1628 (in Chinese).
11. Liu T.F., Shen Q L. Eur. J. Org. Chem. 2012, 6679.
12. Welch J.T. Tetrahedron 1987, 43, 3123.
13. Kirsch O. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, Wiley-VCH, Weinheim, 2004.
14. Shimizu M., Hiyama T. Angew. Chem., Int. Ed. 2005, 44, 214.
15. Schlosser M. Angew. Chem., Int. Ed. 2006, 45, 5432.
16. Muller K., Faeh C., Diederich F. Science 2007, 317, 1881.
17. Bonnet-Delpon D. Bioorganic and Medicinal Chemistry of Fluorine, Wiley-VCH, Hoboken, NJ, 2008.
18. Purser S., Moore O.R., Swallow S., Gouverneur V. Chem. Soc. Rev. 2008, 37, 320.
19. Hagmann W.K. J. Med. Chem. 2008, 51, 4359.
20. Pursor S., Moore O.R., Swallow S., Gouverneur V. Chem. Soc. Rev. 2008, 37, 320.
21. Ojima I. Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, Chichester, 2009.
22. Lin G.-Q., You Q.-D., Cheng J.-F. Chiral Drugs: Chemistry and Biological Action, Wiley-VCH, Hoboken, 2011.
23. Swarts F. Bull. Acad. R. Belg. 1892, 24, 309.
24. Boswell G.A., Jr., Ripka W.C., Scribner R.M., Tullock C.W. Org. React. 1974, 21, 1.
25. Kazuyuki S., Masaaki O., Akira A., Itsumaro K. Org. Lett. 2013, 23, 4359.
26. Mizuta S., Verhoog S., Engle K.M., Khotavivattana T., O'Duill M., Wheelhouse K., Rassias G., Medebielle M., Gouverneur V. J. Am. Chem. Soc. 2013, 135, 2505.
27. Yasu Y., Koike T., Akita M. Org. Lett. 2013, 15, 2137.
28. Herrmann A.T., Smith L.L., Zakarian A. J. Am. Chem. Soc. 2012, 134, 6976.
29. Iqbal N., Choi S., Kim E., Cho E.J. J. Org. Chem. 2012, 77, 11383.
30. Mizuta S., Engle K.M., Verhoog S., Galicia-López O., O'Duill M., Médebielle M., Wheelhouse K., Rassias G., Thompson A.L., Gouverneur V. Org. Lett. 2013, 15, 1250.
31. Wang X., Truesdale L., Yu J.-Q. J. Am. Chem. Soc. 2010, 132, 3648.
32. Ye Y., Ball N.D., Kampf J.W., Sanford M.S. J. Am. Chem. Soc. 2010, 132, 14682.
33. Ball N.D., Gary J.B., Ye Y., Sanford M.S. J. Am. Chem. Soc. 2011, 133, 7577.
34. Cho E.J., Buchwald S.L. Org. Lett. 2011, 13, 6552.
35. Hafner A., Brase S. Angew. Chem., Int. Ed. 2012, 51, 3713.
36. Zhang X.G., Dai H.X., Wasa M., Yu J.Q. J. Am. Chem. Soc. 2012, 134, 11948.
37. Hafner A., Bihlmeier A., Nieger M., Klopper W., Brase S. J. Org. Chem. 2013, 78, 7938.
38. Hafner A., Feuerstein T.J., Bräse S. Org. Lett. 2013, 15, 3468.
39. Ye Y., Lee S.H., Sanford M.S. Org. Lett. 2011, 13, 5464.
40. Wang X., Xu Y., Mo F., Ji G., Qiu D., Feng J., Ye Y., Zhang S., Zhang Y., Wang J. J. Am. Chem. Soc. 2013, 135, 10330.
41. Zeng Y., Zhang L., Zhao Y., Ni C., Zhao J., Hu J. J. Am. Chem. Soc. 2013, 135, 2955.
42. Dubinina G.G., Brennessel W.W., Miller J.L., Vicic D.A. Organometallics 2008, 27, 3933.
43. Hao F., Jiang H.W., Zong G., Zhou Z., Du R.B., Chen Q.Y., Xiao J.C. J. Org. Chem. 2012, 77, 3604.
44. Gao J.R., Wu H., Xiang B., Yu W.B., Han L., Jia Y.X. J. Am. Chem. Soc. 2013, 135, 2983.
45. Parsons A.T., Senecal T.D., Buchwald S.L. Angew. Chem., Int. Ed. 2012, 51, 2947.
46. Patra T., Deb A., Manna S., Sharma U., Maiti D. Eur. J. Org. Chem. 2013, 2013, 5247.
47. Kobayashi Y., Kumadaki I. Tetrahedron Lett. 1969, 10, 4095.
48. Kobayashi Y., Yamamoto K., Kumadaki I. Tetrahedron Lett. 1979, 20, 4071.
49. Kondratenko N.U., Vechirko E.P., Yagupolskii L.M. Synthesis 1980, 932.
50. Kremlev M.M., Tyrra W., Mushta A.I., Naumann D., Yagupolskii Y.L. J. Fluorine Chem. 2010, 131, 212.
51. Nowak I., Robins M.J. J. Org. Chem. 2007, 72, 2678.
52. Burton D.J., Wiemers D.M. J. Am. Chem. Soc. 1985, 107, 5014.
53. Burton D.J., Wiemers D.M. J. Am. Chem. Soc. 1986, 108, 832.
54. Clark J.H., McClinton M.A., Blade R.J. J. Chem. Soc., Chem. Commun. 1988, 638.
55. Carr G.E., Chambers R.D., Holmes T.F., Parker D.G. J. Chem. Soc., Perkin Trans. 1 1988, 921
56. Su D.B., Duan J.X., Chen Q.Y. Tetrahedron Lett. 1991, 32, 7689.
57. Chen Q.Y., Duan J.X. J. Chem. Soc., Chem. Commun. 1993, 1389.
58. McLoughlin V.C.R., Thrower J. Tetrahedron 1969, 25, 5921.
59. Lin T.S., Gao Y.S. J. Med. Chem. 1983, 26, 598.
60. Duan J.X., Su D.B., Wu J.P., Chen Q.Y. J. Fluorine Chem. 1994, 66, 167.
61. Su D.B., Duan J.X., Chen Q.Y. Tetrahedron Lett. 1991, 32, 7689.
62. Su D.B., Duan J.X., Yu A., Chen Q.Y. J. Fluorine Chem. 1993, 65, 11.
63. Langlois B.R., Roques N. J. Fluorine Chem. 2007, 128, 1318.
64. Qing F. Chin. J. Org. Chem. 2012, 32, 815 (in Chinese).
65. Yang C.-T., Zhang Z.-Q., Liu Y.-C., Liu L. Angew. Chem., Int. Ed. 2011, 50, 3904.
66. Yang C.-T., Zhang Z.-Q., Liang J., Liu J.-H., Lu X.-Y., Chen H.-H., Liu L. J. Am. Chem. Soc. 2012, 134, 11124.
67. Yang C.-T., Zhang Z.-Q., Tajuddin H., Wu C.-C., Liang J., Liu J.-H., Fu Y., Czyzewska M., Steel O.G., Marder T.B., Liu L. Angew. Chem., Int. Ed. 2012, 51, 528.
68. Ren P., Stern L.-A., Hu X. Angew. Chem., Int. Ed. 2012, 51, 9110.
69. Nishino M., Hirano K., Satoh T., Miura M. Angew. Chem., Int. Ed. 2012, 51, 6993.
70. Wu J.-C., Song R.-J., Wang Z.-Q., Huang X.-C., Xie Y.-X., Li J.-H. Angew. Chem., Int. Ed. 2012, 51, 6993.
71. Kitching M.O., Hurst T.E., Snieckus V. Angew. Chem., Int. Ed. 2012, 51, 2925.
72. Wang L., Huang H., Priebbenow D.L., Pan F.-F., Bolm C. Angew. Chem., Int. Ed. 2013, 52, 3478.
73. Uyeda C., Tan Y., Fu G.C., Peters J.C. J. Am. Chem. Soc. 2013, 135, 9548.
74. Deng W., Liu L., Guo Q.-X. Chin. J. Org. Chem. 2004, 24, 150 (in Chinese).
75. Xu H.-J., Man Q.-S., Lin Y.-C., Li Y.-Y., Feng Y.-S. Chin. J. Org. Chem. 2010, 30, 9 (in Chinese).
76. Dubinina G.G., Furutachi H., Vicic D.A. J. Am. Chem. Soc. 2008, 130, 8600.
77. Oishi M., Kondo H., Amii H. Chem. Commun. 2009, 1909.
78. Zhang S.-L., Liu L., Fu Y., Guo Q.-X. Organometallics 2007, 26, 4546.
79. Morimoto H., Tsubogo T., Litvinas N.D., Hartwig J.F. Angew. Chem., Int. Ed. 2011, 50, 3793.
80. Zanardi A., Novikov M.A., Martin E., Benet-Buchholz J., Grushin V.U. J. Am. Chem. Soc. 2011, 133, 20901.
81. Tomashenko O.A., Escudero-Adan E.C., Belmonte M.M., Grushin V.U. Angew. Chem., Int. Ed. 2011, 50, 7655.
82. 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.
83. Weng Z., Lee R., Jia W., Yuan Y., Wang W., Feng X., Huang K.W. Organometallics 2011, 30, 3229.
84. Kondo H., Oishi M., Fujikawa K., Amii H. Adv. Synth. Catal. 2011, 353, 1247.
85. Knauber T., Arikan F., Roschenthaler G.-V., Goossen L. J. Chem. Eur. J. 2011, 17, 2689.
86. Schareina T., Wu X.-F., Zapf A., Cotté A., Gotta M., Beller M. Top. Catal. 2012, 55, 426.
87. Duan C., Li Y., Chen T., Wang H., Zhang R., Jin K., Wang X. Synlett 2011, 1713.
88. Chen M., Buchwald S.L. Angew. Chem., Int. Ed. 2013, 52, 11628.
89. Hafner A., Braese S. Adv. Synth. Catal. 2011, 353, 3044.
90. Kawai H., Furukawa T., Nomura Y., Tokunaga E., Shibata N. Org. Lett. 2011, 13, 3596.
91. Miyake Y., Ota S., Nishibayashi Y. Chem.-Eur. J. 2012, 18, 13255.
92. Miyake Y., Ota S., Shibata M., Nakajima K., Nishibayashi Y. Chem. Commum. 2013, 49, 7809.
93. Larsson J.M., Pathipati S.R., Szabo K.J. J. Org. Chem. 2013, 78, 7330.
94. Zhao T.S., Szabo K. J. Org. Lett. 2012, 14, 3966.
95. Novak P., Lishchynskyi A., Grushin V.U. J. Am. Chem. Soc. 2012, 134, 16167.
96. Ambler B.R., Altman R.A. Org. Lett. 2013.
97. Chu L., Qing F.-L. Org. Lett. 2010, 12, 5060.
98. Senecal T.D., Parsons A.T., Buchwald S.L. J. Org. Chem. 2011, 76, 1174.
99. Xu J., Luo D.F., Xiao B., Liu Z.J., Gong T.J., Fu Y., Liu L. Chem. Commun. 2011, 47, 4300.
100. Zhang C.P., Cai J., Zhou C.B., Wang X.P., Zheng X., Gu Y.C., Xiao J.C. Chem. Commun. 2011, 47, 9516.
101. Liu T., Shen Q. Org. Lett. 2011, 13, 2342.
102. Huang Y., Fang X., Lin X., Li H., He W., Huang K.-W., Yuan Y., Weng Z. Tetrahedron 2012, 68, 9949.
103. 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.
104. Ye Y., Künzi S.A., Sanford M.S. Org. Lett. 2012, 14, 4979.
105. Li Y., Wu L., Neumann H., Beller M. Chem. Commun. 2013, 49, 2628.
106. Litvinas N.D., Fier O.S., Hartwig J.F. Angew. Chem., Int. Ed. 2012, 51, 536.
107. Liu T., Shao X., Wu Y., Shen Q. Angew. Chem., Int. Ed. 2012, 51, 555.
108. Novák P., Lishchynskyi A., Grushin V.U. Angew. Chem., Int. Ed. 2012, 51, 7767.
109. Khan B.A., Buba A.E., Goossen L.J. Chem.-Eur. J. 2012, 18, 1577.
110. Ye Y., Sanford M.S. J. Am. Chem. Soc. 2012, 134, 9034.
111. Xu J., Xiao B., Xie C.Q., Luo D.F., Liu L., Fu Y. Angew. Chem., Int. Ed. 2012, 51, 12551.
112. Zheng H., Huang Y., Wang Z., Li H., Huang K.-W., Yuan Y., Weng Z. Tetrahedron Lett. 2012, 53, 6646.
113. Chu L., Qing F.-L. J. Am. Chem. Soc. 2010, 132, 7262.
114. Weng Z., Li H., He W., Yao L.-F., Tan J., Chen J., Yuan Y., Huang K.-W. Tetrahedron 2012, 68, 2527.
115. Luo D.-F., Xu J., Fu Y., Guo Q.-X. Tetrahedron Lett. 2012, 53, 2769.
116. Zhang K., Qiu X.-L., Huang Y., Qing F.-L. Eur. J. Org. Chem. 2012, 58.
117. Shimizu R., Egami H., Nagi T., Chae J., Hamashima Y., Sodeoka M. Tetrahedron Lett. 2010, 51, 5947.
118. Chu L., Qing F.L. J. Am. Chem. Soc. 2012, 134, 1298.
119. Pair E., Monteiro N., Bouyssi D., Baudoin O. Angew. Chem., Int. Ed. 2013, 52, 5346.
120. Feng C., Loh T.-P. Chem. Sci. 2012, 3, 3458.
121. Ilchenko N.O., Janson O.G., Szabo K. J. Chem. Commun. 2013, 49, 6614.
122. Wang X., Ye Y., Ji G., Xu Y., Zhang S., Feng J., Zhang Y., Wang J. Org. Lett. 2013, 15, 3730.
123. 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.
124. Parsons A.T., Buchwald S.L. Angew. Chem., Int. Ed. 2011, 50, 9120.
125. Wang X., Ye Y., Zhang S., Feng J., Xu Y., Zhang Y., Wang J. J. Am. Chem. Soc. 2011, 133, 16410.
126. Chu L., Qing F.-L. Org. Lett. 2010, 14, 2106.
127. Mitsudera H., Li C.-J. Tetrahedron Lett. 2011, 52, 1898.
128. Chu L.L., Qing F.L. Chem. Commun. 2010, 46, 6285.
129. Xiao H.Q., Huang Y.Z., Qing F.-L. Tetrahedron 2010, 21, 2949.
130. Hu M., Ni C., Hu J. J. Am. Chem. Soc. 2012, 134, 15257.
131. Dai J.J., Fang C., Xiao B., Yi J., Xu J., Liu Z.J., Lu X., Liu L., Fu Y. J. Am. Chem. Soc. 2013, 135, 8436.
132. Danoun G., Bayarmagnai B., Grunberg M.F., Goossen L. J. Angew. Chem., Int. Ed. 2013, 52, 7972.
133. Shang R., Liu L. Sci. China Chem. 2011, 54, 1670.
134. Shang R., Fu Y., Li J.-B., Zhang S.-L., Guo Q.-X., Liu L. J. Am. Chem. Soc. 2009, 131, 5738.
135. Shang R., Yang Z.W., Wang Y., Zhang S.-L., Liu L. J. Am. Chem. Soc. 2010, 132, 14391.
136. Dai J.-J., Liu J.-H., Luo D.-F., Liu L. Chem. Commun. 2011, 47, 677.
137. Li Z.J., Cui Z.L., Liu Z.Q. Org. Lett. 2013, 15, 406.
138. He Z., Luo T., Hu M., Cao Y., Hu J. Angew. Chem., Int. Ed. 2012, 51, 3944.
139. He Z., Zhang R., Hu M., Li L., Ni C., Hu J. Chem. Sci. 2012, 4, 3478.
140. Anna E. A., David W.C., MacMillan D.W.C. J. Am. Chem. Soc. 2012, 132, 4986.
141. Nagib D.A., Scott M.E., MacMillan D.W.C. J. Am. Chem. Soc. 2009, 131, 10875.
142. Nagib D.A., MacMillan D.W.C. Nature 2011, 480, 224.
143. Pham O.U., Nagib D.A., MacMillan D.W.C. Angew. Chem., Int. Ed. 2011, 50, 6119.
144. Prier C.K., Rankic D.A., MacMillan D.W.C. Chem. Rev. 2013, 113, 5322.
145. Deng Q.H., Wadepohl H., Gade L.H. J. Am. Chem. Soc. 2012, 134, 10769.
146. Janson O.G., Ghoneim I., Ilchenko N.O., Szabó K. J. Org. Lett. 2012, 14, 2882.
147. Zhu R., Buchwald S.L. J. Am. Chem. Soc. 2012, 134, 12462.
148. Ilchenko N.O., Janson O.G., Szabo K.J. J. Org. Chem. 2013, 78, 11087.
149. Kong W., Casimiro M., Merino E., Nevado C. J. Am. Chem. Soc. 2013, 135, 14480.
150. Egami H., Shimizu R., Sodeoka M. J. Fluorine Chem. 2013, 152, 51.
151. Zhang Y.Q., Liu J.D., Xu H. Org. Biomol. Chem. 2013, 11, 6242.
152. Liu X., Xiong F., Huang X., Xu L., Li P., Wu X. Angew. Chem., Int. Ed. 2013, 52, 6962.
153. Chen Z.M., Bai W., Wang S.H., Yang B.M., Tu Y.Q., Zhang F.M. Angew. Chem., Int. Ed. 2013, 52, 9781.
154. Qing F.-L., Chu L. Synthesis 2012, 44, 1521.
155. Lin X., Wang G., Li H., Huang Y., He W., Ye D., Huang K.-W., Yuan Y., Weng Z. Tetrahedron 2013, 69, 2628.