Copper-mediated oxidative trifluoromethylation of boronic acids

Organic Letters

Volumn 12, Issue 21, 2010, Pages 5060-5063

  Chu, Lingling ^a   Qing, Feng Ling ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b DONGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; COPPER; FLUORINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METHYLATION; OXIDATION REDUCTION REACTION;

BORONIC ACIDS; COPPER; FLUORINE COMPOUNDS; METHYLATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 78049501331     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1023135     Document Type: Article

References (74)

1. Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2005, 44, 214
2. Schlosser, M. Angew. Chem., Int. Ed. 2006, 45, 5432
3. Ma, J.-A.; Cahard, D. J. Fluorine Chem. 2007, 128, 975
4. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
5. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
6. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359
7. Kirk, K. L. Org. Process. Res. Dev. 2008, 12, 305
8. Swarts, F. Bull. Acad. R. Belg. 1892, 24, 309
9. Boswell, G. A., Jr.; Ripka, W. C.; Scribner, R. M.; Tullock, C. W. Org. React 1974, 21, 1
10. For selected Cu-mediated trifluoromethylations, see
11. Kobayashi, Y.; Kumadaki, I. Tetrahedron Lett. 1969, 10, 4095
12. Konderatenko, N. V.; Vechirko, E. P.; Yagupolskii, L. M. Synthesis 1980, 932
13. Matsui, K.; Tobita, E.; Ando, M.; Kondo, K. Chem. Lett. 1981, 1719
14. Suzuki, H.; Yoshida, Y.; Osuka, A. Chem. Lett. 1982, 135
15. Burton, D. J.; Wiemers, D. M. J. Am. Chem. Soc. 1985, 107, 5014
16. Umemoto, T.; Ando, A. Bull. Chem. Soc. Jpn. 1986, 59, 447
17. Carr, G. E.; Chambers, R. D.; Holmes, T. F.; Parker, D. G. J. Chem. Soc., Perkin Trans. 1988, 921
18. Urata, H.; Fuchikami, T. Tetrahedron Lett. 1991, 32, 91
19. Long, Z.-Y.; Duan, J.-X.; Lin, Y.-B.; Guo, C.-Y.; Chen, Q.-Y. J. Fluorine Chem. 1996, 78, 177
20. Cottet, F.; Schlosser, M. Eur. J. Org. Chem. 2002, 327
21. Xiao, J.-C.; Ye, C.; Shreeve, J. M. Org. Lett. 2005, 7, 1963
22. Langlois, B. R.; Roques, N. J. Fluorine Chem. 2007, 128, 1318
23. Dubinina, G. G.; Furutachi, H.; Vicic, D. A. J. Am. Chem. Soc. 2008, 130, 8600
24. Dubinina, G. G.; Ogikubo, J.; Vicic, D. A. Organometallics. 2008, 27, 6233
25. For copper-catalyzed trifluoromethylations, see
26. Chen, Q.-Y.; Wu, S.-W. Chem. Commun. 1989, 705
27. Oishi, M.; Kondo, H.; Amii, H. Chem. Commun. 2009, 1909
28. Wakselman, C.; Tordeux, M. J. Chem. Soc., Chem. Commun. 1987, 1701
29. Laglois, B. R.; Laurent, E.; Roidot, M. Tetrahedron Lett. 1991, 32, 7525
30. Mace, Y.; Raymondeau, B.; Pradet, C.; Blazejewski, J. C.; Magnier, E. Eur. J. Org. Chem. 2009, 1390
31. Wiehn, M. S.; Vinogradova, E. V.; Togni, A. J. Fluorine Chem. 2010, 131, 951
32. Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679
33. Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 2878
34. Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2006, 128, 12644
35. Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2006, 128, 4632
36. For Pd(II)-catalyzed arene trifluoromethylation reaction via C-H activation, see:
37. Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648
38. Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine; Hall, D. G., Eds.; Wiley-VCH: Weinheim, 2005.
39. For selected recent examples, see:
40. Chan, D. M. T.; Lam, P. Y. S. In Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine; Hall, D. G., Eds.; Wiley-VCH: Weinheim, 2005; pp 205 - 240.
41. Singh, B. K.; Appukkutta, P.; Claerhout, S.; Parmar, V. S.; Van der Eycken, E. Org. Lett. 2006, 8, 1863
42. Liu, J.; Naruta, Y.; Tani, F. Chem.-Eur. J. 2007, 13, 6365
43. Tao, C. Z.; Cui, X.; Li, J.; Liu, A. X.; Liu, L.; Guo, Q. X. Tetrahedron Lett. 2007, 48, 3525
44. Vogler, T.; Studer, A. Org. Lett. 2008, 10, 129
45. Zhang, Z.; Yu, Y.; Liebeskind, L. S. Org. Lett. 2008, 10, 3005
46. Benard, S.; Neuville, L.; Zhu, J. J. Org. Chem. 2008, 73, 6441
47. King, A. E.; Brunold, T. C.; Stahl, S. S. J. Am. Chem. Soc. 2009, 131, 5044
48. Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. Angew. Chem., Int. Ed. 2009, 48, 1114
49. Zhou, C.; Yang, D.; Jia, X.; Zhang, L.; Cheng, J. Synlett 2009, 3198
50. Mahoney, M. E.; Oliver, A.; Einarsdottir, O.; Konopelski, J. P. J. Org. Chem. 2009, 74, 8212
51. Shade, R. E.; Hyde, A. M.; Olsen, J. C.; Merlic, C. A. J. Am. Chem. Soc. 2010, 132, 1202
52. Zhao, X.; Jing, J.; Lu, K.; Zhang, Y.; Wang, J. Chem. Commun. 2010, 1724
53. Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. Adv. Synth. Catal. 2010, 352, 45
54. Grimes, K. D.; Gupte, A.; Aldrich, C. C. Synthesis 2010, 1441
55. DalZotto, C.; Michaux, J.; Martinand-Lurin, E.; Campagne, J. M. Eur. J. Org. Chem. 2010, 3811
56. Liskey, C. W.; Liao, X.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 11389
57. Chan, D. M. T.; Monaco, K. L.; Wang, R. P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933
58. Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937
59. Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941
60. Furuya, T.; Kaiser, H. M.; Ritter, T. Angew. Chem., Int. Ed 2008, 47, 5993
61. Furuya, T.; Ritter, T. Org. Lett. 2009, 11, 2860
62. Cazorla, C.; Metay, E.; Andrioletti, B.; Lemaire, M. Tetrahedron Lett. 2009, 50, 3936
63. Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2010, 132, 7262
64. The phenols were observed in many metal-catalyzed couplings of phenylboronic acids in the presence of oxygen
65. Yoo, K. S.; Yoon, C. H.; Jung, K. W. J. Am. Chem. Soc. 2006, 128, 16384
66. Chaicharoenwimolkul, L.; Munmai, A.; Chairam, S.; Tewasekson, U.; Sapudom, S.; Lakliang, Y.; Somsook, E. Tetrahedron Lett. 2008, 49, 7299
67. Xu, J.; Wang, X.; Shao, C.; Su, D.; Cheng, G.; Hu, Y. Org. Lett. 2010, 12, 1964
68. 18O-labeling studies have shown that a phenol byproduct arises from water serving as an oxygen nucleophile
69. Lam, P. Y. S.; Bonne, D.; Vincent, G.; Clark, C. G.; Combs, A. P. Tetrahedron Lett. 2003, 44, 1691
70. King, A. E.; Huffman, L. M.; Casitas, A.; Costas, M.; Ribas, X.; Stahl, S. S. J. Am. Chem. Soc. 2010, 132, 12068
71. Huffman, L. M.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 9196
72. Snyder, J. Angew. Chem., Int. Ed. 1995, 34, 80
73. Lipshutz, B. H.; Siegmann, K.; Garcia, E.; Kayser, F. J. Am. Chem. Soc. 1993, 115, 9276
74. Willert-Porada, D. M.; Burton, D. J.; Baenziger, N. C. J. Chem. Soc., Chem. Commun. 1989, 1633