Copper-catalyzed trifluoromethylation of aryl- and vinylboronic acids with generation of CF3-radicals

Chemical Communications

Volumn 49, Issue 26, 2013, Pages 2628-2630

  Li, Yang ^a   Wu, Lipeng ^a   Neumann, Helfried ^a   Beller, Matthias ^a  

^a LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLBORONIC ACID; BORONIC ACID DERIVATIVE; COPPER; UNCLASSIFIED DRUG; VINYLBORONIC ACID;

ARTICLE; ATMOSPHERE; CATALYSIS; CHEMICAL REACTION; ELECTRON; RADICAL REACTION; ROOM TEMPERATURE; TRIFLUOROMETHYLATION;

EID: 84874881615     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc36554e     Document Type: Article

References (71)

1. M.Schlosser, Angew.Chem, Int. Ed, 2006, 45:5432
2. K.Müller, C.Faeh, F.Diederich, Science, 2007, 317:1881
3. W. K.Hagmann, J. Med. Chem, 2008, 51:4359
4. K. L.Kirk, Org. Process Res. Dev, 2008, 12:305
5. S.Purser, P. R.Moore, S.Swallow, V.Gouverneur, Chem. Soc. Rev, 2008, 37:320
6. V. V.Grushin, Acc. Chem. Res, 2010, 43:160
7. R. J.Lundgren, M.Stradiotto, Angew. Chem, Int. Ed, 2010, 49:9322
8. S.Roy, B. T.Gregg, G. W.Gribble, V.-D.Le, Tetrahedron, 2011, 67:2161
9. O. A.Tomashenko, V. V.Grushin, Chem. Rev, 2011, 111:4475
10. T.Besset, C.Schneider, D.Cahard, Angew. Chem, Int. Ed, 2012, 51:5048
11. X.-F.Wu, H.Neumann, M.Beller, Chem.Asian J, 2012, 7:1744
12. G. G.Dubinina, H.Furutachi, D. A.Vicic, J.Am. Chem. Soc, 2008, 130:8600
13. G. G.Dubinina, J.Ogikubo, D. A.Vicic, Organometallics, 2008, 27:6233
14. M.Oishi, H.Kondo, H. Amii, Chem. Commun, 2009, 1909
15. E. J.Cho, T. D.Senecal, T.Kinzel, Y.Zhang, D. A.Watson, S. L.Buchwald, Science, 2010, 328:1679
16. A.Zanardi, M. A.Novikov, E.Martin, J.Benet-Buchholz, V. V.Grushin, J.Am. Chem. Soc, 2011, 133:20901
17. C.-P.Zhang, Z.-L.Wang, Q.-Y.Chen, C.-T.Zhang, Y.-C.Gu, J.-C.Xiao, Angew. Chem, Int. Ed, 2011, 50:1896
18. H.Morimoto, T.Tsubogo, N. D.Litvinas, J. F.Hartwig, Angew. Chem, Int. Ed, 2011, 50:3793
19. O. A.Tomashenko, E. C.Escudero-Adán, M.Martínez Belmonte, V. V.Grushin, Angew. Chem, Int. Ed, 2011, 50:7655
20. H.Kondo, M.Oishi, K.Fujikawa, H.Amii, Adv. Synth. Catal, 2011, 353:1247
21. Z.Weng, R.Lee, W.Jia, Y.Yuan, W.Wang, X.Feng, K.-W.Huang, Organometallics, 2011, 30:3229
22. T.Knauber, F.Arikan, G.-V.Röschenthaler, L. J.Gooßen, Chem.Eur. J, 2011, 17:2689
23. Y.Li, T.Chen, H.Wang, R.Zhang, K.Jin, X.Wang, C. Duan, Synlett, 2011, 1713
24. B. S.Samant, G. W.Kabalka, Chem. Commun, 2011, 47:7236
25. T.Schareina, X.-F.Wu, A.Zapf, A.Cotte, M.Gotta, M.Beller, Top. Catal, 2012, 55:426
26. L.Chu, F.-L.Qing, Org. Lett, 2010, 12:5060
27. T. D.Senecal, A. T.Parsons, S. L.Buchwald, J. Org. Chem, 2011, 76:1174
28. T.Liu, Q.Shen, Org. Lett, 2011, 13:2342
29. J.Xu, D.-F.Luo, B.Xiao, Z.-J.Liu, T.-J.Gong, Y.Fu, L.Liu, Chem. Commun, 2011, 47:4300
30. C.-P.Zhang, J.Cai, C.-B.Zhou, X.-P.Wang, X.Zheng, Y.-C.Gu, J.-C.Xiao, Chem. Commun, 2011, 47:9516
31. X.Jiang, L.Chu, F.-L.Qing, J. Org. Chem, 2012, 77:1251
32. B. A.Khan, A. E.Buba, L. J.Gooßen, Chem.Eur. J, 2012, 18:1577
33. N. D.Litvinas, P. S.Fier, J. F.Hartwig, Angew. Chem, Int. Ed, 2012, 51:536
34. T.Liu, X.Shao, Y.Wu, Q.Shen, Angew. Chem, Int. Ed, 2012, 51:540
35. P.Novák, A.Lishchynskyi, V. V.Grushin, Angew. Chem, Int. Ed, 2012, 51:7767
36. X.Wang, L.Truesdale, J.-Q.Yu, J.Am. Chem. Soc, 2010, 132:3648
37. X.-G.Zhang, H.-X.Dai, M.Wasa, J.-Q.Yu, J.Am. Chem. Soc, 2012, 134:11948
38. A.Hafner, S.Bräse, Angew. Chem, Int. Ed, 2012, 51:3713
39. X.Mu, S.Chen, X.Zhen, G.Liu, Chem.Eur. J, 2011, 17:6039
40. L.Chu, F.-L.Qing, J.Am. Chem. Soc, 2012, 134:1298
41. B. R.Langlois, E.Laurent, N. Roidot, Tetrahedron Lett, 1991, 32:7525
42. N.Kamigata, T.Ohtsuka, T.Fukushima, M.Yoshida, T.Shimizu, J.Chem. Soc, Perkin Trans. 1, 1994, 1339
43. D. A.Nagib, D. W. C. MacMillan, Nature, 2011, 480:224
44. Y.Ji, T.Brueckl, R. D.Baxter, Y.Fujiwara, I. B.Seiple, S.Su, D. G.Blackmond, P. S.Baran, Proc. Natl. Acad. Sci. U. S. A, 2011, 108:14411
45. Y.Ye, S. H.Lee, M. S.Sanford, Org. Lett, 2011, 13:5464
46. B. R.Langlois, E.Laurent, N. Roidot, Tetrahedron Lett, 1992, 33:1291
47. Y.Ye, M. S.Sanford, J.Am. Chem. Soc, 2012, 134:9034
48. Q.Qi, Q.Shen, L.Lu, J.Am. Chem. Soc, 2012, 134:6548
49. Y.Ye, S. A.Künzi, M. S.Sanford, Org. Lett, 2012, 14:4979
50. H. G.Kuivila, A. G.Armour, J.Am. Chem. Soc, 1957, 79:5659
51. V. V.Grushin, W. J.Marshall, J.Am. Chem. Soc, 2006, 128:4632
52. V. V.Grushin, W. J.Marshall, J.Am. Chem. Soc, 2006, 128:12644
53. N. D.Ball, J. W.Kampf, M. S.Sanford, J.Am. Chem. Soc, 2010, 132:2878
54. Y.Ye, N. D.Ball, J. W.Kampf, M. S.Sanford, J.Am. Chem. Soc, 2010, 132:14682
55. N. D.Ball, J. B.Gary, Y.Ye, M. S.Sanford, J.Am. Chem. Soc, 2011, 133:7577
56. X.Mu, T.Wu, H.-Y.Wang, Y.-L.Guo, G.Liu, J.Am. Chem. Soc, 2012, 134:878
57. M.Shimizu, Y.Takeda, M.Higashi, T.Hiyama, Angew. Chem, Int. Ed, 2009, 48:3653
58. T.Kitazume, N.Ishikawa, J.Am. Chem. Soc, 1985, 107:5186
59. Q.-Y.Chen, S.-W.Wu, J. Chem. Soc, Chem. Commun, 1989, 705
60. Q.-Y.Chen, J.-X.Duan, J. Chem. Soc, Chem. Commun, 1993, 1389
61. J.Duan, D.Su, Q.Chen, J. Fluorine Chem, 1993, 61:279
62. T.Hanamoto, N.Morita, K. Shindo, Eur. J. Org. Chem, 2003, 4279
63. X.-G.Zhang, M.-W.Chen, P.Zhong, M.-L.Hu, J. Fluorine Chem, 2008, 129:335
64. S. M.Landge, D. A.Borkin, B.Torok, Lett. Org. Chem, 2009, 6:439
65. A.Hafner, S.Bräse, Adv. Synth. Catal, 2011, 353:3044
66. A. T.Parsons, T. D.Senecal, S. L.Buchwald, Angew. Chem, Int. Ed, 2012, 51:2947
67. G. K. S.Prakash, H. S.Krishnan, P. V.Jog, A. P.Iyer, G. A.Olah, Org. Lett, 2012, 14:1146
68. C.Feng, L.-P.Loh, Chem. Sci, 2012, 3:3458
69. C.Chen, Y.Xie, L.Chu, R.-W.Wang, X.Zhang, F.-L.Qing, Angew. Chem, Int. Ed, 2012, 51:2492
70. W.-Y.Yu, W. N.Sit, Z.Zhou, A. S. C.Chan, Org. Lett, 2009, 11:3174
71. D.Kalyani, K. B.McMurtrey, S. R.Neufeldt, M. S.Sanford, J.Am. Chem. Soc, 2011, 133:18566