Selective C4-F bond cleavage of pentafluorobenzene: Synthesis of N-tetrafluoroarylated heterocyclic compounds

Tetrahedron Letters

Volumn 54, Issue 35, 2013, Pages 4649-4652

  Liu, Cuibo ^a   Wang, Huan ^a   Xing, Xing ^a   Xu, You ^a   Ma, Jun An ^a   Zhang, Bin ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

C F cleavage; Fluorine chemistry; N heterocycles; Polyfluoroarenes

Indexed keywords

FLUOROBENZENE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CONTROLLED STUDY; SYNTHESIS;

EID: 84880770687     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.06.055     Document Type: Article

References (73)

1. J. Nie, H.C. Guo, D. Cahard, and J.A. Ma Chem. Rev. 111 2011 455
2. F. Wang, T. Luo, J. Hu, Y. Wang, H.S. Krishan, P.V. Jog, S.K. Ganesh, G.K.S. Prakash, and G.A. Olah Angew. Chem., Int. Ed. 50 2011 7153
3. J.M. Racowski, J.B. Gary, and M.S. Sanford Angew. Chem. 124 2012 3470
4. T. Furuya, A.S. Kamlet, and T. Ritter Nature 473 2010 470
5. Y.L. Liu, T.D. Shi, F. Zhou, X.L. Zhao, X. Wang, and J. Zhou Org. Lett. 13 2011 3826
6. D.A. Nagib, and D.W.C. MacMillan Nature 480 2011 224
7. O. Allemann, S. Duttwyler, P. Romanto, K.K. Baldridge, and J.S. Siegel Science 332 2011 574
8. H. Amii, and K. Uneyama Chem. Rev. 109 2009 2119
9. A.R. Murphy, and J.M.J. Fréchet Chem. Rev. 107 2007 1066
10. F. Babudri, G.M. Farinola, F. Naso, and R. Ragni Chem. Commun. 2007 1003
11. K. Müller, C. Faeh, and F. Diederich Science 2007 1881 317
12. E.A. Meyer, R.K. Castellano, and F. Diederich Angew. Chem., Int. Ed. 42 2003 1210
13. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320
14. B.M. Kraft, and W.D. Jones J. Am. Chem. Soc. 124 2002 8681
15. M. Lafrance, D. Shore, and K. Fagnou Org. Lett. 8 2006 5097
16. H.-Q. Do, and O. Daugulis J. Am. Chem. Soc. 130 2008 1128
17. Y. Nakao, N. Kashihara, K.S. Kanyiva, and T. Hiyama J. Am. Chem. Soc. 130 2008 16170
18. S.A. Johnson, C.W. Huff, F. Mustafa, and M. Saliba J. Am. Chem. Soc. 130 2008 17278
19. M.E. Doster, and S.A. Johnson Angew. Chem., Int. Ed. 48 2009 2185
20. C.Y. He, S. Fan, and X. Zhang J. Am. Chem. Soc. 132 2010 12850
21. Y. Wei, and W.P. Su J. Am. Chem. Soc. 132 2010 16377
22. I. Popov, S. Lindeman, and O. Daugulis J. Am. Chem. Soc. 133 2011 9286
23. A. Nakatani, K. Hirano, T. Satoh, and M. Miura Org. Lett. 14 2012 2586
24. M. Aizenberg, and D. Milstein J. Am. Chem. Soc. 117 1995 8674
25. P. Barrio, R. Castarlenas, M.A. Esteruelas, A. Lledos, F. Maseras, E. Onate, and J. Tomas Organometallics 20 2001 442
26. G. Ferrando-Miguel, H. Gerard, O. Eisenstein, and K.G. Caulton Inorg. Chem. 41 2002 6440
27. J. Vela, J.M. Smith, Y. Yu, N.A. Ketterer, C.J. Flaschenriem, R.J. Lachicotte, and P.L. Holland J. Am. Chem. Soc. 127 2005 7857
28. L. Zhang, W. Zhang, J. Liu, and J.B. Hu J. Org. Chem. 74 2009 2850
29. A. Sun, and J.L. Love Dalton Trans. 39 2010 10362
30. E. Clot, O. Eisenstein, N. Jasim, S.A. Macgregor, J.E. Mcgrady, and R.N. Perutz Acc. Chem. Res. 44 2011 333
31. A.G. O'Brien, Z. Horvth, F. Lévesque, J.W. Lee, A. Seidel-Morgenstern, and P.H. Seeberger Angew. Chem., Int. Ed. 51 2012 7028
32. H. Jasch, S.B. Höf ling, and M.R. Heinrich J. Org. Chem. 77 2012 1520
33. Y. Nakamura, N. Yoshikai, L. Ilies, and E. Nakamura Org. Lett. 14 2012 3316
34. J.H. Zhang, H. Lv, Y. Yu, and J.L. Zhang Adv. Synth. Catal. 354 2012 1529
35. W. Zhao, J. Wu, and S. Cao Adv. Synth. Catal. 354 2012 574
36. D. Yu, Q.L. Shen, and L. Lu J. Org. Chem. 77 2012 1798
37. T. Schaub, M. Backes, and U. Radius J. Am. Chem. Soc. 128 2006 15964
38. B.D. Palmer, J.B. Smaill, M. Boyd, D.H. Boschelli, A.M. Doherty, J.M. Hamby, S.S. Khatana, J.B. Kramer, A.J. Kraker, R.L. Panek, G.H. Lu, T.K. Dahring, R.T. Winters, H.D. Showalter, and W.A. Denny J. Med. Chem. 41 1998 5457
39. W.Y. Wong Coord. Chem. Rev. 249 2005 971
40. F. Ullmann Ber. Dtsch. Chem. Ges. 36 1903 2382
41. I. Goldberg Ber. Dtsch. Chem. Ges. 39 1906 1691
42. M.S. Driver, and J.F. Hartwig J. Am. Chem. Soc. 119 1997 8232
43. D. Ma, and C. Xia Org. Lett. 3 2001 2583
44. J.C. Antilla, A. Klapars, and S.L. Buchwald J. Am. Chem. Soc. 124 2002 11684
45. D. Ma, and Q. Cai Synlett 2004 128
46. R.A. Altman, and S.L. Buchwald Org. Lett. 8 2006 2779
47. A.A. Kantak, S. Potavathri, R.A. Barham, K.M. Romano, and B. Deboef J. Am. Chem. Soc. 133 2011 19960
48. E.T. Nadres, and O. Daugulis J. Am. Chem. Soc. 134 2012 7
49. M. Yamamoto, and S. Matsubara Chem. Lett. 36 2007 172
50. J.A. Jordan-Hore, C.C.C. Johansson, M. Gulias, E.M. Beck, and M.J. Gaunt J. Am. Chem. Soc. 130 2008 16184
51. A.P. Antonchick, R. Samanta, K. Kulikov, and J. Lategahn Angew. Chem., Int. Ed. 50 2011 8605
52. C. Desmarets, R. Schneider, and Y. Fort J. Org. Chem. 67 2002 3029
53. G. Toma, K.I. Fujita, and R. Yamaguchi Eur. J. Org. Chem. 2009 4586
54. M. Taillefer, N. Xia, and A. Ouali Angew. Chem., Int. Ed. 46 2007 934
55. Y.C. Teo Adv. Synth. Catal. 351 2009 720
56. M.C. Venuti, R.A. Stephenson, R. Alvarez, J.J. Bruno, and A.M. Strosberg J. Med. Chem. 31 1988 2136
57. R. Bambal, and R.P. Haznlik J. Org. Chem. 59 1994 729
58. J.X. Qiao, X. Cheng, D.P. Modi, K.A. Rossi, J.M. Luettgen, R.M. Knabb, P.K. Jadhav, and R.R. Wexler Bioorg. Med. Chem. Lett. 15 2005 29
59. P.Y.S. Lam, S. Deudon, K.M. Averill, R. Li, M.Y. He, P. DeShong, and C.G. Clark J. Am. Chem. Soc. 122 2000 7600
60. G.I. Elliott, and J.P. Konopelski Org. Lett. 2 2000 3055
61. G.M. Brooke, J. Burdon, M. Stacey, and J.C. Tatlow J. Chem. Soc. 1960 1768
62. J.M. Birchall, R.N. Haszeldine, and A.R. Parkinson J. Chem. Soc. 1962 4966
63. S. Fujii, Y. Maki, and H. Kimoto J. Fluorine Chem. 43 1989 131
64. W.S. Chow, and T.H. Chan Tetrahedron Lett. 50 2009 1286
65. M.W. Cartwright, L. Convery, T. Kraynck, G. Sandford, D.S. Yufit, J.A.K. Howard, J.A. Christopher, and D.D. Miller Tetrahedron 66 2010 519
66. M. Otsuka, K. Endo, and T. Shibata Chem. Commun. 2010 336
67. R. Cano, D.J. Ramón, and M. Yus J. Org. Chem. 76 2011 654
68. F. Diness, and D.P. Fairlie Angew. Chem., Int. Ed. 51 2012 8012
69. G. Sandford, A. Tadeusiak, D.S. Yufit, and J.A.K. Howard J. Fluorine Chem. 128 2007 1216
70. R. Stahlmann Toxicol. Lett. 127 2002 269
71. B.-R.-M. Kim, T.-J. Lee, H.-J. Lee, B.-H. Park, and B.-M. Yang Value Health Reg. Issues 1 2012 59
72. M.A. Balón, M.C. Carmona, M.A. Muñoz, and J. Hidalgo Tetrahedron 45 1989 7501
73. M.A. Muñoz, P. Guardado, J. Hidalgo, M.C. Carmona, and M.A. Balón Tetrahedron 48 1992 5901