Carbon-fluorine bond activation for the synthesis of functionalized molecules

Tetrahedron Letters

Volumn 56, Issue 7, 2015, Pages 877-883

  Unzner, Teresa A ^a   Magauer, Thomas ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

C F bond activation; Catalysis; Fluorine; Medicinal chemistry

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; AMIDE; ANILINE DERIVATIVE; AROMATIC AMINE; BENZENE DERIVATIVE; BENZOPHENONE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; COPPER; CYCLOPENTADIENE DERIVATIVE; FLUORINE DERIVATIVE; FURAN DERIVATIVE; HYDRAZINE DERIVATIVE; MAGNESIUM; NICKEL; NUCLEOPHILE; PALLADIUM; PLATINUM; PYRAZOLE DERIVATIVE;

ALKYLATION; ALLYLATION; ALLYLIC REARRANGEMENT; AMINATION; CARBON FLUORINE BOND; CATALYSIS; CHEMICAL BOND; CHEMICAL INTERACTION; CLAISEN REARRANGEMENT; CYCLIZATION; DEFLUORINATION; ELECTROPHILICITY; HYDROGEN BOND; MOLECULE; REVIEW; SUZUKI REACTION; SYNTHESIS;

EID: 84921452990     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.12.145     Document Type: Review

References (79)

1. H.-J. Böhm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Müller, U. Obst-Sander, and M. Stahl ChemBioChem 5 2004 637 643
2. K. Müller, C. Faeh, and F. Diederich Science 317 2007 1881 1886
3. J. Burdeniuc, B. Jedlicka, and R.H. Crabtree Chem. Ber. Recueil 130 1997 145 154
4. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320 330
5. J. Wang, M. Sánchez-Roselló, J.L. Aceña, C. del Pozo, A.E. Sorochinsky, S. Fustero, V.A. Soloshonok, and H. Liu Chem. Rev. 114 2014 2432 2506
6. T. Liang, C.N. Neumann, and T. Ritter Angew. Chem. 125 2013 8372 8423
7. Angew. Chem. Int. Ed. 52 2013 8214 8264
8. D. O'Hagan Chem. Soc. Rev. 37 2008 308 319
9. S.J. Blanksby, and G.B. Ellison Acc. Chem. Res. 36 2003 255 263
10. For selected examples see: (a) T. Hiyama, M. Obayashi, and M. Sawahata Tetrahedron Lett. 24 1983 4113 4116
11. D.E. Bergstrom, M.W. Ng, and J.J. Wong J. Org. Chem. 48 1983 1902 1903
12. T. Fuchikami, Y. Shibata, and Y. Suzuki Tetrahedron Lett. 27 1986 3173 3176
13. T. Kitazume, and T. Ohnogi Synthesis 1988 614 615
14. T. Kitazume, T. Ohnogi, H. Miyauchi, and T. Yamazaki J. Org. Chem. 54 1989 5630 5632
15. D.A. Kendrick, and M. Kolb J. Fluorine Chem. 45 1989 265 272
16. J.-P. Bégué, D. Bonnet-Delpon, and M.H. Rock Tetrahedron Lett. 36 1995 5003 5006
17. J.-P. Bégué, D. Bonnet-Delpon, and M.H. Rock J. Chem. Soc. Perkin Trans. 1 1996 1409 1413
18. J. Ichikawa, Y. Ishibashi, and H. Fukui Tetrahedron Lett. 44 2003 707 710
19. J. Ichikawa, R. Nadano, and N. Ito Chem. Commun. 2006 4425 4427
20. M. Bergeron, T. Johnson, and J.-F. Paquin Angew. Chem. 123 2011 11308 11312
21. Angew. Chem. Int. Ed. 50 2011 11112 11116
22. G.-Q. Shi, X.-H. Huang, and F.-J. Zhang Tetrahedron Lett. 36 1995 6305 6308
23. T. Narumi, K. Tomita, E. Inokuchi, K. Kobayashi, S. Oishi, H. Ohno, and N. Fujii Org. Lett. 9 2007 3465 3468
24. L. Hintermann, F. Läng, P. Maire, and A. Togni Eur. J. Inorg. Chem. 2006 1397 1412
25. A. Hazari, V. Gouverneur, and J.M. Brown Angew. Chem. 121 2009 1322 1325
26. Angew. Chem. Int. Ed. 48 2009 1296 1299
27. Y. Nakamura, M. Okada, H. Horikawa, and T. Taguchi J. Fluorine Chem. 117 2002 143 148
28. M. Okada, Y. Nakamura, A. Saito, A. Sato, H. Horikawa, and T. Taguchi Tetrahedron Lett. 43 2002 5845 5847
29. M. Okada, Y. Nakamura, A. Saito, A. Sato, H. Horikawa, and T. Taguchi Chem. Lett. 2002 28 29
30. Y. Nakamura, M. Okada, A. Sato, H. Horikawa, M. Koura, A. Saito, and T. Taguchi Tetrahedron 61 2005 5741 5753
31. A. Otaka, E. Mitsuyama, H. Watanabe, H. Tamarura, and N. Fujii Chem. Commun. 2000 1081 1082
32. A. Otaka, H. Watanabe, E. Mitsuyama, A. Yukimasa, H. Tamamura, and N. Fujii Tetrahedron Lett. 42 2001 285 287
33. A. Otaka, H. Watanabe, A. Yukimasa, S. Oishi, H. Tamamura, and N. Fujii Tetrahedron Lett. 42 2001 5443 5446
34. Y. Nakamura, M. Okada, H. Horikawa, and T. Taguchi J. Fluorine Chem. 117 2002 143 148
35. T. Narumi, K. Tomita, E. Inokuchi, K. Kobayashi, S. Oishi, H. Ohno, and N. Fujii Tetrahedron 64 2008 4332 4346
36. A. Otaka, J. Watanabe, A. Yukimasa, Y. Sasaki, H. Watanabe, T. Kinoshita, S. Oishi, H. Tamamura, and N. Fujii J. Org. Chem. 69 2004 1634 1645
37. Y. Yamaki, A. Shigenaga, J. Li, Y. Shimohigashi, and A. Otaka J. Org. Chem. 74 2009 3278 3285
38. Y. Yamaki, A. Shigenaga, K. Tomita, T. Narumi, N. Fujii, and A. Otaka J. Org. Chem. 74 2009 3272 3277
39. H. Amii, and K. Uneyama Chem. Rev. 109 2009 2119 2183
40. E. Clot, O. Eisenstein, N. Jasmin, S.A. Mcgregor, J.E. McGRady, and R.N. Perutz Acc. Chem. Res. 44 2001 333 348
41. J. Weaver, and S. Senaweera Tetrahedron 70 2014 7413 7428
42. K. Fuchibe, M. Takahashi, and J. Ichikawa Angew. Chem. 124 2012 12225 12228
43. Angew. Chem. Int. Ed. 51 2012 12059 12062
44. T. Ichitsuka, T. Fujita, T. Arita, and J. Ichikawa Angew. Chem. 126 2014 7694 7698
45. Angew. Chem. Int. Ed. 53 2014 7564 7568
46. X. Pigeon, M. Bergeron, F. Barabé, P. Dubé, H.N. Frost, and J.-F. Paquin Angew. Chem. 122 2010 1141 1145
47. Angew. Chem. Int. Ed. 49 2010 1123 1127
48. T. Konno, K. Nagata, T. Ishihara, and H. Yamanaka J. Org. Chem. 67 2002 1768 1775
49. J. Xu, X.-L. Qiu, and F.-L. Qing Beilstein J. Org. Chem. 4 2008 18 19
50. For selected examples see: (a) R.J. Abraham, S.L.R. Ellison, P. Schonholzer, and W.A. Thomas Tetrahedron 42 1986 2101 2110
51. A. Niida, K. Tomita, M. Mizumoto, H. Tanigaki, T. Terada, S. Oishi, A. Otaka, K.-I. Inui, and N. Fuji Org. Lett. 8 2006 613 616
52. P. Van der Veken, K. Senten, I. Kertèsz, I. De Meester, A.-M. Lambeir, M.-B. Maes, S. Scharpé, A. Haemers, and K. Augustyns J. Med. Chem. 48 2005 1768 1780
53. M. Shimizu, T. Fujimoto, H. Minezaki, T. Hata, and T. Hiyama J. Am. Chem. Soc. 123 2001 6947 6948
54. M. Shimizu, T. Fujimoto, X. Liu, H. Minezaki, T. Hata, and T. Hiyama Tetrahedron 59 2003 9811 9823
55. H. Plenio Chem. Rev. 97 1997 3363 3384
56. 2) is strongly exothermic. For lattice energy values see: S. Zhang, H. Li, S. Zhou, and T. Pan Jpn. J. Appl. Phys. 45 2006 8801 8804
57. M. Bergeron, D. Guyader, and J.-F. Paquin Org. Lett. 14 2012 5888 5891
58. J.-D. Hamel, M. Drouin, and J.-F. Paquin J. Fluorine Chem. 2014 10.1016/j.jfluchem.2014.07.012
59. H. Yanai, H. Okada, A. Sato, M. Okada, and T. Taguchi Tetrahedron Lett. 52 2011 2997 3000
60. D. Watanabe, M. Koura, A. Saito, H. Yanai, Y. Nakamura, M. Okada, A. Sato, and T. Taguchi J. Fluorine Chem. 132 2011 327 338
61. Y.Y. Hong, J.H. Kim, S.J. Choi, and I.H. Jeong J. Fluorine Chem. 155 2013 83 88
62. E. Benedetto, M. Keita, M. Tredwell, C. Hollingworth, J.M. Brown, and V. Gouverneur Organometallics 31 2012 1408 1416
63. T. Nishimine, K. Fukushi, N. Shibata, H. Taira, E. Tokunaga, A. Yamano, M. Shiro, and N. Shibata Angew. Chem. 126 2014 527 530
64. Angew. Chem. Int. Ed. 53 2014 517 520
65. T. Kobayashi, T. Nakagawa, H. Amii, and K. Uneyama Org. Lett. 5 2003 4297 4300
66. G. Takikawa, T. Katagiri, and K. Uneyama J. Org. Chem. 70 2005 8811 8816
67. Y. Nakamura, Y. Ozeki, and K. Uneyama J. Fluorine Chem. 129 2008 274 279
68. For a review, see K. Uneyama, and H. Amii J. Fluorine Chem. 114 2002 127 131
69. S. Utsumi, T. Katagiri, and K. Uneyama J. Fluorine Chem. 152 2013 84 89
70. G. Blessley, P. Holden, M. Walker, J.M. Brown, and V. Gouverneur Org. Lett. 14 2012 2754 2757
71. Selected examples: (a) L. Strekowski, J.L. Mokrosz, V.A. Honkan, A. Czarny, M.T. Cegla, R.L. Wydra, S.E. Patterson, and R.F. Schinazi J. Med. Chem. 34 1991 1739 1746
72. A.S. Kiselyov, and L. Strekowski Org. Prep. Proc. Int. 28 1966 289 318
73. L. Strekowski, R.L. Wydra, M.T. Cegla, A. Czarny, D.B. Harden, S.E. Patterson, M.A. Battiste, and J.M. Coxon J. Org. Chem. 55 1990 4777 4779
74. A.S. Kiselyov, and L. Strekowski Tetrahedron Lett. 35 1994 7597 7600
75. J. Zhang, J. Sączewskia, E. Wolińska, and L. Strekowski Heterocycl. Commun. 19 2013 245 247
76. J. Zhang, J. Sączewskia, E. Wolińska, and L. Strekowski Heterocycl. Commun. 19 2013 357 362
77. J. Hammann, T.A. Unzner, and T. Magauer Chem. Eur. J. 20 2014 6733 6738
78. P.A. Champagne, J. Pomarole, M.-E. Thérien, Y. Benhassine, S. Beaulieu, C.Y. Legault, and J.-F. Paquin Org. Lett. 15 2013 2210 2213
79. P.A. Champagne, A. Saint-Martin, M. Drouin, and J.-F. Paquin Beilstein J. Org. Chem. 9 2013 2451 2456