Copper-catalyzed tandem trifluoromethylation/semipinacol rearrangement of allylic alcohols

Angewandte Chemie - International Edition

Volumn 52, Issue 37, 2013, Pages 9781-9785

  Chen, Zhi Min ^a   Bai, Wei ^a   Wang, Shao Hua ^a   Yang, Bin Miao ^a   Tu, Yong Qiang ^a   Zhang, Fu Min ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

trifluoromethyl ketone; copper; fluorine; semipinacol rearrangement; trifluoromethylation

Indexed keywords

ALLYLIC ALCOHOL; DIFUNCTIONALIZATION; QUATERNARY CARBON; REARRANGEMENT REACTIONS; SEMIPINACOL REARRANGEMENT; STRAIGHTFORWARD STRATEGY; TRIFLUOROMETHYLATION; TRIFLUOROMETHYLKETONE;

CATALYSIS; FLUORINE; KETONES;

COPPER;

ALLYL ALCOHOL; COPPER; CYCLOHEXENE DERIVATIVE; FLUORINE; PROPANOL; SEMIPINACOL;

ARTICLE; CATALYSIS; CHEMISTRY; METHYLATION; SEMIPINACOL REARRANGEMENT; TRIFLUOROMETHYLATION; Β-TRIFLUOROMETHYL KETONE;

COPPER; FLUORINE; SEMIPINACOL REARRANGEMENT; TRIFLUOROMETHYLATION; Β-TRIFLUOROMETHYL KETONE;

CATALYSIS; COPPER; CYCLOHEXENES; FLUORINE; METHYLATION; PROPANOLS;

EID: 84883545162     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201304557     Document Type: Article

References (137)

1. T. Yamazaki, T. Taguchi, I. Ojima, in Fluorine in Medicinal Chemistry and Chemical Biology (Ed.:, I. Ojima,), Wiley-Blackwell, Chichester, 2009, p. 3
2. M. Schlosser, Angew. Chem. 2006, 118, 5558
3. Angew. Chem. Int. Ed. 2006, 45, 5432
4. K. Müller, C. Faeh, F. Diederich, Science 2007, 317, 1881
5. K. William, W. K. Hagmann, J. Med. Chem. 2008, 51, 4359
6. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320
7. K. L. Kirk, Org. Process Res. Dev. 2008, 12, 305.
8. T. Umemoto, Chem. Rev. 1996, 96, 1757
9. G. K. S. Prakash, A. K. Yudin, Chem. Rev. 1997, 97, 757
10. M. Shimizu, T. Hiyama, Angew. Chem. 2005, 117, 218
11. Angew. Chem. Int. Ed. 2005, 44, 214
12. J.-A. Ma, D. Cahard, Chem. Rev. 2008, 108, PR 1
13. T. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470
14. O. A. Tomashenko, V. V. Grushin, Chem. Rev. 2011, 111, 4475
15. X.-F. Wu, H. Neumann, M. Beller, Chem. Asian J. 2012, 7, 1744
16. Y. Ye, M. S. Sanford, Synlett 2012, 2005
17. T. Besset, C. Schneider, D. Cahard, Angew. Chem. 2012, 124, 5134
18. Angew. Chem. Int. Ed. 2012, 51, 5048
19. A. Studer, Angew. Chem. 2012, 124, 9082
20. Angew. Chem. Int. Ed. 2012, 51, 8950.
21. J. Xu, B. Xiao, C.-Q. Xie, D.-F. Luo, L. Liu, Y. Fu, Angew. Chem. 2012, 124, 12719
22. Angew. Chem. Int. Ed. 2012, 51, 12551
23. S. P. Fritz, T. H. West, E. M. McGarrigle, V. K. Aggarwal, Org. Lett. 2012, 14, 6370
24. Y. Miyake, S. Ota, Y. Nishibayashi, Chem. Eur. J. 2012, 18, 13255
25. A. T. Parsons, T. D. Senecal, S. L. Buchwald, Angew. Chem. 2012, 124, 3001
26. Angew. Chem. Int. Ed. 2012, 51, 2947
27. Z. He, T. Luo, M. Hu, Y. Cao, J. Hu, Angew. Chem. 2012, 124, 4010
28. Angew. Chem. Int. Ed. 2012, 51, 3944.
29. I. Kieltsch, P. Eisenberger, A. Togni, Angew. Chem. 2007, 119, 768
30. Angew. Chem. Int. Ed. 2007, 46, 754
31. D. A. Nagib, M. E. Scott, D. W. C. MacMillan, J. Am. Chem. Soc. 2009, 131, 10875
32. A. E. Allen, D. W. C. MacMillan, J. Am. Chem. Soc. 2010, 132, 4986
33. P. V. Pham, D. A. Nagib, D. W. C. Macmillan, Angew. Chem. 2011, 123, 6243
34. Angew. Chem. Int. Ed. 2011, 50, 6119
35. B. Morandi, E. M. Carreira, Angew. Chem. 2011, 123, 9251
36. Angew. Chem. Int. Ed. 2011, 50, 9085
37. A. T. Herrmann, L. L. Smith, A. Zakarian, J. Am. Chem. Soc. 2012, 134, 6976
38. Q.-H. Deng, H. Wadepohl, L. H. Gade, J. Am. Chem. Soc. 2012, 134, 10769
39. M. Hu, C. Ni, J. Hu, J. Am. Chem. Soc. 2012, 134, 15257
40. P. Novák, A. Lishchynskyi, V. V. Grushin, J. Am. Chem. Soc. 2012, 134, 16167.
41. M. S. Wiehn, E. V. Vinogradova, A. Togni, J. Fluorine Chem. 2010, 131, 951
42. X. Wang, L. Truesdale, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 3648
43. D. A. Nagib, D. W. C. MacMillan, Nature 2011, 480, 224
44. Y. Ye, S. H. Lee, M. S. Sanford, Org. Lett. 2011, 13, 5464
45. R. N. Loy, M. S. Sanford, Org. Lett. 2011, 13, 2548
46. X. Mu, S. Chen, X. Zhen, G. Liu, Chem. Eur. J. 2011, 17, 6039
47. Y. Ji, T. BrueckI, R. D. Baxter, Y. Fujiwara, I. B. Seiple, S. Su, D. G. Blackmond, P. S. Baran, Proc. Natl. Acad. Sci. USA 2011, 108, 14411
48. A. Hafner, S. Bräse, Angew. Chem. 2012, 124, 3773
49. Angew. Chem. Int. Ed. 2012, 51, 3713
50. X.-G. Zhang, H.-X. Dai, M. Wasa, J.-Q. Yu, J. Am. Chem. Soc. 2012, 134, 11948
51. L. Chu, F.-L. Qing, J. Am. Chem. Soc. 2012, 134, 1298
52. E. Mejía, A. Togni, ACS Catal. 2012, 2, 521
53. Y. Fujiwara, J. A. Dixon, F. O'Hara, E. D. Funder, D. D. Dixon, R. A. Rodriguez, R. D. Baxter, B. Herlé, N. Sach, M. R. Collins, Y. Ishihara, P. S. Baran, Nature 2012, 492, 95
54. L.-S. Zhang, K. Chen, G. Chen, B.-J. Li, S. Luo, Q.-Y. Guo, J.-B. Wei, Z.-J. Shi, Org. Lett. 2013, 15, 10.
55. M. Oishi, H. Kondo, H. Amii, Chem. Commun. 2009, 1909
56. E. J. Cho, T. D. Senecal, T. Kinzel, Y. Zhang, D. A. Watson, S. L. Buchwald, Science 2010, 328, 1679
57. H. Morimoto, T. Tsubogo, N. D. Litvinas, J. F. Hartwig, Angew. Chem. 2011, 123, 3877
58. Angew. Chem. Int. Ed. 2011, 50, 3793
59. T. Knauber, F. Arikan, G.-V. Röschenthaler, L. Gooßn, Chem. Eur. J. 2011, 17, 2689
60. C.-P. Zhang, Z.-L. Wang, Q.-Y. Chen, C.-T. Zhang, Y.-C. Gu, J.-C. Xiao, Angew. Chem. 2011, 123, 1936
61. Angew. Chem. Int. Ed. 2011, 50, 1896
62. A. Zanardi, M. A. Novikov, E. Martin, J. Benet-Buchholz, V. V. Grushin, J. Am. Chem. Soc. 2011, 133, 20901
63. O. A. Tomashenko, E. C. Escudero-Adán, M. M. Belmonte, V. V. Grushin, Angew. Chem. 2011, 123, 7797
64. Angew. Chem. Int. Ed. 2011, 50, 7655
65. M. Döbele, M. S. Wiehn, S. Bräse, Angew. Chem. 2011, 123, 11737
66. Angew. Chem. Int. Ed. 2011, 50, 11533
67. I. Popov, S. Lindeman, O. Daugulis, J. Am. Chem. Soc. 2011, 133, 9286
68. B. S. Samant, G. W. Kabalka, Chem. Commun. 2011, 47, 7236.
69. L. Chu, F.-L. Qing, Org. Lett. 2010, 12, 5060
70. J. Xu, D.-F. Luo, B. Xiao, Z.-J. Liu, T.-J. Gong, Y. Fu, L. Liu, Chem. Commun. 2011, 47, 4300
71. T. Liu, Q. Shen, Org. Lett. 2011, 13, 2342
72. T. D. Senecal, A. T. Parsons, S. L. Buchwald, J. Org. Chem. 2011, 76, 1174
73. T. Liu, X. Shao, Y. Wu, Q. Shen, Angew. Chem. 2012, 124, 555
74. Angew. Chem. Int. Ed. 2012, 51, 540
75. N. D. Litvinas, P. S. Fier, J. F. Hartwig, Angew. Chem. 2012, 124, 551
76. Angew. Chem. Int. Ed. 2012, 51, 536
77. P. Novák, A. Lishchynskyi, V. V. Grushin, Angew. Chem. 2012, 124, 7887
78. Angew. Chem. Int. Ed. 2012, 51, 7767
79. Y. Ye, M. S. Sanford, J. Am. Chem. Soc. 2012, 134, 9034
80. Q. Qi, Q. Shen, L. Lu, J. Am. Chem. Soc. 2012, 134, 6548
81. Y. Li, L. Wu, H. Neumann, M. Beller, Chem. Commun. 2013, 49, 2628.
82. H. Kawai, Y. Sugita, E. Tokunaga, H. Sato, M. Shiro, N. Shibata, Chem. Commun. 2012, 48, 3632
83. N. Shibata, T. Nishimine, N. Shibata, E. Tokunaga, K. Kawada, T. Kagawa, A. E. Sorochinsky, V. A. Soloshonok, Chem. Commun. 2012, 48, 4124.
84. D. V. Sevenard, V. Y. Sosnovskikh, A. A. Kolomeitsev, M. H. Königsmann, G.-V. Röschenthaler, Tetrahedron Lett. 2003, 44, 7623
85. V. Y. Sosnovskikh, B. I. Usachev, D. V. Sevenard, G.-V. Röschenthaler, J. Org. Chem. 2003, 68, 7747
86. V. Y. Sosnovskikh, B. I. Usachev, D. V. Sevenard, G.-V. Röschenthaler, Tetrahedron Lett. 2003, 44, 2097
87. A. D. Dilman, V. V. Levin, P. A. Belyakov, M. I. Stuchkova, V. A. Tartakovsky, Tetrahedron Lett. 2008, 49, 4352
88. A. A. Zemtsov, V. V. Levin, A. D. Dilman, M. I. Stuchkova, P. A. Belyakov, V. A. Tartakovsky, Tetrahedron Lett. 2009, 50, 2998
89. A. A. Zemtsov, V. V. Levin, A. D. Dilman, M. I. Stuchkova, P. A. Belyakov, V. A. Tartakovsky, J. Hu, Eur. J. Org. Chem. 2010, 6779
90. R. Shimizu, H. Egami, Y. Hamashima, M. Sodeoka, Angew. Chem. 2012, 124, 4655
91. Angew. Chem. Int. Ed. 2012, 51, 4577
92. S. Mizuta, O. Galicia-Lõpez, K. M. Engle, S. Verhoog, K. Wheelhouse, G. Rassias, V. Gouverneur, Chem. Eur. J. 2012, 18, 8583
93. N. Iqbal, S. Choi, E. Kim, E. J. Cho, J. Org. Chem. 2012, 77, 11383
94. Y. Yasu, T. Koike, M. Akita, Angew. Chem. 2012, 124, 9705
95. Angew. Chem. Int. Ed. 2012, 51, 9567.
96. A. T. Parsons, S. L. Buchwald, Angew. Chem. 2011, 123, 9286
97. Angew. Chem. Int. Ed. 2011, 50, 9120
98. 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
99. X. Wang, Y. Ye, S. Zhang, J. Feng, Y. Xu, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2011, 133, 16410
100. L. Chu, F.-L. Qing, Org. Lett. 2012, 14, 2106
101. X. Wu, L. Chu, F.-L. Qing, Angew. Chem. 2013, 125, 2254
102. Angew. Chem. Int. Ed. 2013, 52, 2198
103. S. Mizuta, S. Verhoog, K. M. Engle, T. Khotavivattana, M. O'Duill, K. Wheelhouse, G. Rassias, M. Médebielle, V. Gouverneur, J. Am. Chem. Soc. 2013, 135, 2505.
104. P. G. Janson, I. N. Ghoneim, O. Ilchenko, K. J. Szabõ, Org. Lett. 2012, 14, 2882
105. C. Feng, T.-P. Loh, Chem. Sci. 2012, 3, 3458
106. R. Zhu, S. L. Buchwald, J. Am. Chem. Soc. 2012, 134, 12462
107. H. Egami, R. Shimizu, M. Sodeoka, Tetrahedron Lett. 2012, 53, 5503.
108. X. Mu, T. Wu, H. Wang, Y. Guo, G. Liu, J. Am. Chem. Soc. 2012, 134, 878
109. H. Egami, R. Shimizu, S. Kawamura, M. Sodeoka, Angew. Chem. 2013, 125, 4092
110. Angew. Chem. Int. Ed. 2013, 52, 4000
111. During the revision of this manuscript, related research on copper-catalyzed trifluoromethylation-initiated radical 1,2-aryl migration in α,α-diaryl allylic alcohols was published: X. Liu, F. Xiong, X. Huang, L. Xu, P. Li, X. Wu, Angew. Chem. 2013, 125, 7100;
112. Angew. Chem. Int. Ed. 2013, 52, 6962.
113. L. A. Paquette, D. R. Owen, R. T. Bibart, C. K. Seekamp, A. L. Kahane, J. C. Lanter, M. A. Corral, J. Org. Chem. 2001, 66, 2828
114. P. B. Hurley, G. R. Dake, J. Org. Chem. 2008, 73, 4131
115. S. A. Snyder, Z.-Y. Tang, R. Gupta, J. Am. Chem. Soc. 2009, 131, 5744
116. Z.-L. Song, C.-A. Fan, Y.-Q. Tu, Chem. Rev. 2011, 111, 7523.
117. B. Rickborn, in Comprehensive Organic Synthesis, Vol. 3 (Eds:, B. M. Trost, I. Fleming,), Pergamon, Oxford, 1991, p. 721
118. L. E. Overman, Acc. Chem. Res. 1992, 25, 352
119. T. J. Snape, Chem. Soc. Rev. 2007, 36, 1823
120. B. Wang, Y.-Q. Tu, Acc. Chem. Res. 2011, 44, 1207.
121. B. M. Trost, J. Xie, J. Am. Chem. Soc. 2006, 128, 6044
122. Q.-W. Zhang, C.-A. Fan, H.-J. Zhang, Y.-Q. Tu, Y.-M. Zhao, P. Gu, Z.-M. Chen, Angew. Chem. 2009, 121, 8724
123. Angew. Chem. Int. Ed. 2009, 48, 8572
124. F. Kleinbeck, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 9178
125. E. Zhang, C.-A. Fan, Y.-Q. Tu, F.-M. Zhang, Y.-L. Song, J. Am. Chem. Soc. 2009, 131, 14626
126. Z.-M. Chen, Q.-W. Zhang, Z.-H. Chen, H. Li, Y.-Q. Tu, F.-M. Zhang, J.-M. Tian, J. Am. Chem. Soc. 2011, 133, 8818
127. C. Müller, H. M. Wilking, A. Rühlmann, B. Wibbeling, U. Hennecke, Synlett 2011, 2043
128. Z. Chai, T. J. Rainey, J. Am. Chem. Soc. 2012, 134, 3615
129. Z.-M. Chen, B.-M. Yang, Z.-H. Chen, Q.-W. Zhang, M. Wang, Y.-Q. Tu, Chem. Eur. J. 2012, 18, 12950
130. T. Hashimoto, S. Isobe, C. K. A. Callens, K. Maruoka, Tetrahedron 2012, 68, 7630.
131. I. L. Lysenko, H.-S. Oh, J. K. Cha, J. Org. Chem. 2007, 72, 7903
132. A. M. Meyer, C. E. Katz, S.-W. Li, D. V. Velde, J. Aubé, Org. Lett. 2010, 12, 1244
133. R. J. Phipps, L. McMurray, S. Ritter, H. A. Duong, M. J. Gaunt, J. Am. Chem. Soc. 2012, 134, 10773.
134. P. Eisenberger, S. Gischig, A. Togni, Chem. Eur. J. 2006, 12, 2579.
135. T. Umemoto, S. Ishihara, J. Am. Chem. Soc. 1993, 115, 2156.
136. C. S. Aureliano Antunes, M. Bietti, G. Ercolani, O. Lanzalunga, M. Salamone, J. Org. Chem. 2005, 70, 3884.
137. CCDC 919387 (2 g) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.