Metal-free trifluoromethylation of aromatic and heteroaromatic aldehydes and ketones

Journal of Organic Chemistry

Volumn 79, Issue 15, 2014, Pages 7122-7131

  Qiao, Yupu ^a   Si, Tuda ^a   Yang, Ming Hsiu ^a   Altman, Ryan A ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGRICULTURAL ROBOTS; ALDEHYDES; AROMATIC COMPOUNDS; CHEMICAL REACTIONS;

HETEROARENES; HETEROAROMATIC ALDEHYDES; HETEROAROMATIC KETONES; LABOR RESOURCES; MILD REACTION CONDITIONS; MULTISTEP REACTIONS; TRADITIONAL APPROACHES; TRIFLUOROMETHYLATION;

KETONES;

ALDEHYDE; KETONE; POLYCYCLIC AROMATIC HYDROCARBON; FLUORINATED HYDROCARBON; METAL;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DECARBOXYLATION; METHYLATION; OLEFINATION; ONE POT SYNTHESIS; STOICHIOMETRY; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; CATALYSIS; HYDROCARBONS, FLUORINATED; KETONES; METALS; METHYLATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84905388906     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501289v     Document Type: Article

References (94)

1. Kirsch, P. Modern Fluoroorganic Chemistry; Wiley-VCH: Weinheim, Germany, 2004.
2. Uneyama, K. Organofluorine Chemistry; Blackwell: Oxford, U.K., 2006.
3. Tressaud, A. Fluorine and the Environment: Agrochemicals, Archaeology, Green Chemistry & Water; Elsevier: Amsterdam, 2006.
4. Bégué, J.-P.; Bonnet-Delpon, D. Bioorganic and Medicinal Chemistry of Fluorine; John Wiley & Sons, Inc.: Hoboken, NJ, 2008.
5. Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology; John Wiley & Sons, Ltd.: West Sussex, U.K., 2009.
6. Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886
7. Prakash, G. K. S.; Hu, J. Acc. Chem. Res. 2007, 40, 921-930
8. Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305-321
9. Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1-PR43
10. Undgren, R. J.; Stradiotto, M. Angew. Chem., Int. Ed. 2010, 49, 9322-9324
11. Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470-477
12. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475-4521
13. Liu, G. Org. Biomol. Chem. 2012, 10, 6243-6248
14. Hollingworth, C.; Gouverneur, V. Chem. Commun. 2012, 48, 2929-2942
15. Wu, X. F.; Neumann, H.; Beller, M. Chem.-Asian J. 2012, 7, 1744-1754
16. Liu, T.; Shen, Q. Eur. J. Org. Chem. 2012, 6679-6687
17. Besset, T.; Schneider, C.; Cahard, D. Angew. Chem., Int. Ed. 2012, 51, 5048-5050
18. Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem. 2013, 125, 8372-8423
19. Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214-8264
20. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322-5363
21. Qiao, Y.; Zhu, L.; Ambler, B.; Altman, R. A. Curr. Top. Med. Chem. 2014, 14, 966-978
22. Roy, S.; Gregg, B. T.; Gribble, G. W.; Le, V.-D.; Roy, S. Tetrahedron 2011, 67, 2161-2195
23. Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513-1522
24. Liu, H.; Gu, Z.; Jiang, X. Adv. Synth. Catal. 2013, 355, 617-626
25. Chen, P.; Liu, G. Synthesis 2013, 45, 2919-2939
26. Grushin, V. V. Acc. Chem. Res. 2010, 43, 160-171
27. Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 24, 2195-2198
28. Prakash, G. K. S.; Krishnamurti, R.; Olah, G. A. J. Am. Chem. Soc. 1989, 111, 393-395
29. Fustero, S.; Romàn, R.; Sanz-Cervera, J. F.; Simón-Fuentes, A.; Bueno, J.; Villanova, S. J. Org. Chem. 2008, 73, 8545-8552
30. Del Valle, J. R.; Goodman, M. Angew. Chem., Int. Ed. 2002, 41, 1600-1602
31. Jeannot, F.; Gosselin, G.; Mathe, C. Org. Biomol. Chem. 2003, 1, 2096-2102
32. Qiu, X.-L.; Qing, F.-L. J. Org. Chem. 2002, 67, 7162-7164
33. Serafinowski, P. J.; Brown, C. A. Tetrahedron 2000, 56, 333-339
34. Chang, J.; Liu, K.; McEachem, E. J.; Mu, C.; Selenick, H. G.; Shi, F.; Vocaldo, D. J.; Wang, Y.; Wei, Z.; Zhou, Y.; Zhu, Y., Alectos Therapeutics Inc., Can.; Merck Sharp & Dohme Corp., Patent WO 2012062157 A1, 2012.
35. Tam, T. F.; Leung-Toung, R.; Wang, Y.; Zhao, Y., Apotex Technologies Inc., Can., Patent WO 2008116301 A1, 2008.
36. McLoughlin, V. C. R.; Thrower, J. Tetrahedron 1969, 25, 5921-5940
37. Kobayashi, Y.; Yamamoto, K.; Kumadaki, I. Tetrahedron Lett. 1979, 20, 4071-4072
38. Kondratenko, N. V.; Vechirko, E. P.; Yagupolskii, L. M. Synthesis 1980, 932-933
39. Urata, H.; Fuchikami, T. Tetrahedron Lett. 1991, 32, 91-94
40. Chen, Q. Y.; Duan, J. X. J. Chem. Soc., Chem. Commun. 1993, 1389-1391
41. Paratian, J. M.; Labbe, E.; Sibille, S.; Perichon, J. J. Organomet. Chem. 1995, 489, 137-143
42. Kim, J.; Shreeve, J. M. Org. Biomol. Chem. 2004, 2, 2728-2734
43. Dubinina, G. G.; Furutachi, H.; Vicic, D. A. J. Am. Chem. Soc. 2008, 130, 8600-8601
44. Dubinina, G. G.; Ogikubo, J.; Vicic, D. A. Organometallics 2008, 27, 6233-6235
45. Kawai, H.; Furukawa, T.; Nomura, Y.; Tokunaga, E.; Shibata, N. Org. Lett. 2011, 13, 3596-3599
46. Zhu, L.; Liu, S.; Douglas, J. T.; Altman, R. A. Chem.-Eur. J. 2013, 19, 12800-12805
47. Larsson, J. M.; Pathipati, S. R.; Szabó, K. J. J. Org. Chem. 2013, 78, 7330-7336
48. Xu, S.; Chen, H.-H.; Dai, J.-J.; Xu, H.-J. Org. Lett. 2014, 16, 2306-2309
49. Zhao, Y.; Hu, J. Angew. Chem., Int. Ed. 2012, 51, 1033-1036
50. Liang, A.; Li, X.; Liu, D.; Li, J.; Zou, D.; Wu, Y.; Wu, Y. Chem. Commun. 2012, 48, 8273-8275
51. Leng, F.; Wang, Y.; Li, H.; Li, J.; Zou, D.; Wu, Y.; Wu, Y. Chem. Commun. 2013, 49, 10697-10699
52. Fujiwara, Y.; Dixon, J. A.; OHara, F.; Funder, E. D.; Dixon, D. D.; Rodriguez, R. A.; Baxter, R. D.; Herlé, B.; Sach, N.; Collins, M. R.; Ishihara, Y.; Baran, P. S. Nature 2012, 492, 95-99
53. Langlois, B. R.; Laurent, E.; Roidot, N. Tetrahedron Lett. 1991, 32, 7525-7528
54. Fuqua, S. A.; Duncan, W. G.; Silverstein, R. M. Tetrahedron Lett. 1964, 5, 1461-1463
55. Fuqua, S. A.; Duncan, W. G.; Silverstein, R. M. J. Org. Chem. 1965, 30, 1027-1029
56. Herkes, F. E.; Burton, D. J. J. Org. Chem. 1967, 32, 1311-1318
57. Herkes, F. E.; Burton, D. J. Tetrahedron Lett. 1965, 1883-1887
58. Fuqua, S. A.; Duncan, W. G.; Silverstein, R. M. Tetrahedron Lett. 1965, 521-524
59. Fuqua, S. A.; Duncan, W. G.; Silverstein, R. M. J. Org. Chem. 1965, 30, 2543-2545
60. Burton, D. J.; Herkes, F. E.; Klabunde, K. J. J. Am. Chem. Soc. 1966, 88, 5042-5043
61. Naae, D. G.; Burton, D. J. J. Fluorine Chem. 1971, 1, 123-125
62. Naae, D. G.; Burton, D. J. Synth. Commun. 1973, 3, 197-200
63. Burton, D. J.; Yang, Z.-Y.; Qiu, W. Chem. Rev. 1996, 96, 1641-1716
64. Serafinowski, P. J.; Brown, C. A. Tetrahedron 2000, 56, 333-339
65. Nowak, I.; Robins, J. M. Org. Lett. 2005, 7, 721-724
66. Thomoson, C. S.; Martinez, H.; Dolbier, W. R., Jr. J. Fluorine Chem. 2013, 150, 53-59
67. Wang, F.; Li, L.; Ni, C.; Hu, J. Beilstein J. Org. Chem. 2014, 10, 344-351
68. Wang, X.-P.; Lin, J.-H.; Xiao, J.-C.; Zheng, X. Eur. J. Org. Chem. 2014, 928-932
69. Li, Q.; Lin, J.-H.; Deng, Z.-Y.; Zheng, J.; Cai, J.; Xiao, J.-C. J. Fluorine Chem. 2014, 163, 38-41
70. Gao, B.; Zhao, Y.; Hu, M.; Ni, C.; Hu, J. Chem.-Eur. J. 2014, 25, 7803-7810
71. Nguyen, B. V.; Burton, D. J. J. Org. Chem. 1997, 62, 7758-7764
72. Zhu, L.; Li, Y.; Zhao, Y.; Hu, J. Tetrahedron Lett. 2010, 51, 6150-6152
73. Lee, C.-C.; Lin, S.-T. J. Chem. J. Chem. Res. (S) 2000, 142-144
74. Bryan, M. C.; Dilon, B.; Hamann, L. G.; Hughes, G. J.; Kopach, M. E.; Peterson, E. A.; Pourashraf, M.; Raheem, I.; Richardon, P.; Richter, D.; Sneddon, H. F. J. Med. Chem. 2013, 56, 6007-6021
75. Zheng, J.; Cai, J.; Lin, J.-H.; Guo, Y.; Xiao, J.-C. Chem. Commun. 2013, 49, 7513-7515
76. Riss, P. J.; Aigbirhio, F. I. Chem. Commun. 2011, 47, 11873-11875
77. Huang, S.; Petersen, T. B.; Lipshutz, B. H. J. Am. Chem. Soc. 2010, 132, 14021-14023
78. Gong, W.; Singidi, R. R.; Gallucci, J. C.; RajanBabu, T. V. Chem. Sci. 2012, 3, 1221-1230
79. Matthews, D. P.; Whitten, J. P.; McCarthy, J. R. J. Org. Chem. 1986, 51, 3228-3231
80. Yuan, Z.; Que, Z.; Cheng, S.; Zhuo, R.; Li, F. Chem. Commun. 2012, 48, 8129-8131
81. Bromby, A. D.; Jansonius, R. P.; Sutherland, T. C. J. Org. Chem. 2013, 78, 1612-1620
82. Komatsu, T.; Urano, Y.; Fujikawa, Y.; Kobayashi, T.; Kojima, H.; Terai, T.; Hanaoka, K.; Nagano, T. Chem. Commun. 2009, 7015-7017
83. Mack, J.; Bunya, M.; Shimizu, Y.; Uoyama, H.; Komobuchi, N.; Okujima, T.; Uno, H.; Ito, S.; Stillman, M. J.; Ono, N.; Kobayashi, N. Chem.-Eur. J. 2008, 14, 5001-5020
84. Garcia, H.; Gilbert, A.; Griffiths, O. J. Chem. Soc., Perkin Trans. 2 1994, 247-252
85. Sano, H.; Mio, S.; Kitagawa, J.; Sugai, S. Tetrahedron: Asymmetry 1994, 5, 2233-2240
86. Parsons, T. B.; Spencer, N.; Tsanga, C. W.; Grainger, R. S. Chem. Commun. 2013, 49, 2296-2298
87. Wang, W.; Xiong, C.; Zhang, J.; Hruby, V. J. Tetrahedron 2002, 58, 3101-3110
88. Seiple, I. B.; Su, S.; Rodriguez, R. A.; Gianatassio, R.; Fujiwara, Y.; Sobel, A. L.; Baran, P. S. J. Am. Chem. Soc. 2010, 132, 13194-13196
89. Srinivasan, R.; Tan, L. P.; Wu, H.; Yao, S. Q. Org. Lett. 2008, 10, 2295-2298
90. Li, Y.-X.; Luo, Y.-P.; Xi, Z.; Niu, C.; He, Y.-Z.; Yang, G.-F. J. Agric. Food Chem. 2006, 54, 9135-9139
91. Sun, H.-Y.; Xiao, C.-F.; Cai, Y.-C.; Chen, Y.; Wei, W.; Liu, X.-K.; Lv, Z.-L.; Zou, Y. Chem. Pharm. Bull. 2010, 58, 1492-1496
92. Nepomnyashchii, A. B.; Pistner, A. J.; Bard, A. J.; Rosenthal, J. J. Phys. Chem. C 2013, 117, 5599-5609
93. Heidebrecht, R. W., Jr.; Miller, T. A.; Wilson, K. J.; Witter, D. J.; Grimm, J. Patent WO 2007087130 A2, 2007.
94. Leng, F.; Wang, Y.; Li, H.; Li, J.; Zou, D.; Wu, Y.; Wu, Y. Chem. Commun. 2013, 49, 10697-10699