New Prospects toward the Synthesis of Difluoromethylated Phosphate Mimics

Chemistry - A European Journal

Volumn 22, Issue 30, 2016, Pages 10284-10293

  Ivanova, Maria V ^a   Bayle, Alexandre ^a   Besset, Tatiana ^a   Pannecoucke, Xavier ^a   Poisson, Thomas ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

bioisosters; fluorinated phosphonates; fluorine; phosphate mimics; synthetic methods

Indexed keywords

CHEMISTRY; FLUORINE; SYNTHESIS (CHEMICAL);

BIOACTIVE MOLECULES; BIOISOSTERS; PHOSPHONATES; RECENT PROGRESS; SYNTHETIC METHODS;

MOLECULES;

EID: 84977515443     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201601310     Document Type: Article

References (101)

1. R. D. Chambers, Fluorine in Organic Chemistry, Blackwell, Oxford, 2004;
2. K. Uneyama, Organofluorine Chemistry, Blackwell, Oxford, 2006;
3. D. O′Hagan, Chem. Soc. Rev. 2008, 37, 308–319.
4. N. A. Meanwell, J. Med. Chem. 2011, 54, 2529–2591.
5. E. P. Gillis, K. J. Eastman, M. D. Hill, D. J. Donnelly, N. A. Meanwell, J. Med. Chem. 2015, 58, 8315–8359;
6. D. O′Hagan, H. S. Rzepa, Chem. Commun. 1997, 645–652;
7. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320–330.
8. G. Landelle, A. Panossian, S. Pazenok, J.-P. Vors, F. R. Leroux, Beilstein J. Org. Chem. 2013, 9, 2476–2536;
9. T. Ritter, T. Furuya, C. A. Kuttruff, Curr. Opin. Drug Discov. Devel. 2008, 11, 803–819;
10. T. Besset, T. Poisson, X. Pannecoucke, Eur. J. Org. Chem. 2015, 2765–2789;
11. T. Besset, T. Poisson, X. Pannecoucke, Chem. Eur. J. 2014, 20, 16830–16845; for a special issue on fluorine chemistry, see:
12. Chem. Rev. 2015, 115, 563–1306.
13. H. Egami, M. Sodeoka, Angew. Chem. Int. Ed. 2014, 53, 8294–8308;
14. Angew. Chem. 2014, 126, 8434–8449;
15. T. Liang, C. N. Neumann, T. Ritter, Angew. Chem. Int. Ed. 2013, 52, 8214–8264;
16. Angew. Chem. 2013, 125, 8372–8423;
17. T. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470–477;
18. T. Besset, T. Poisson, X. Pannecoucke, J. Fluorine Chem. 2015, 178, 225–240.
19. M.-C. Belhomme, T. Besset, T. Poisson, X. Pannecoucke, Chem. Eur. J. 2015, 21, 12836–12865;
20. C. Ni, L. Zhu, J. Hu, Acta Chim. Sinica 2015, 73, 90–115.
21. For a review, see: V. D. Romanenko, V. P. Kukhar, Chem. Rev. 2006, 106, 3868–3935.
22. D. O′Hagan, H. S. Rzepa, Chem. Commun. 1997, 645–652.
23. G. Thatcher, A. S. Campbell, J. Org. Chem. 1993, 58, 2272–2281.
24. R. D. Chambers, R. Jaouhari, D. O'Hagan, Tetrahedron 1989, 45, 5101–5108.
25. G. M. Blackburn, D. E. Kent, F. Kolkmann, J. Chem. Soc. Chem. Commun. 1981, 1188–1190;
26. G. M. Blackburn, D. E. Kent, F. Kolkmann, J. Chem. Soc. Perkin Trans. 1 1984, 1119–1125.
27. L. Bialy, H. Waldmann, Angew. Chem. Int. Ed. 2005, 44, 3814–3839;
28. Angew. Chem. 2005, 117, 3880–3906;
29. A. P. Combs, J. Med. Chem. 2010, 53, 2333–2344.
30. P. Morlacchi, P. K. Mandal, J. S. McMurray, ACS Med. Chem. Lett. 2014, 5, 69–72;
31. M. Bahta, G. T. Lountos, B. Dyas, S.-E. Kim, R. G. Ulrich, D. S. Waugh, T. R. Burke, Jr., J. Med. Chem. 2011, 54, 2933–2943.
32. C. K. Lau, C. I. Bayly, J. Y. Gauthier, C. S. Li, M. Therien, E. Asante-Appiah, W. Cromlish, Y. Boie, F. Forghani, S. Desmarais, Q. Wang, K. Skorey, D. Waddleton, P. Payette, C. Ramachandran, B. P. Kennedy, G. Scapinc, Bioorg. Med. Chem. Lett. 2004, 14, 1043–1048;
33. T. O. Johnson, J. Ermolieff, M. R. Jirousek, Nat. Rev. Drug. Discovery 2002, 1, 696–709.
34. For selected examples, see:
35. D. J. Burton, R. M. Flynn, J. Fluorine Chem. 1980, 15, 263–266;
36. D. J. Burton, R. M. Flynn, J. Fluorine Chem. 1977, 10, 329–332;
37. R. Waschbüsch, M. Samadi, P. Savignac, J. Organomet. Chem. 1997, 529, 267–278.
38. For selected examples, see:
39. D. E. Bergstrom, P. W. Shum, J. Org. Chem. 1988, 53, 3953–3958;
40. C. F. Bigge, J. T. Drummond, G. Johnson, Tetrahedron Lett. 1989, 30, 7013–7016;
41. M. Obayashi, E. Ito, K. Matsui, K. Kondo, Tetrahedron Lett. 1982, 23, 2323–2326.
42. E. Differding, R. O. Duthaler, A. Krieger, G. M. Rüegg, C. Schmit, Synlett 1992, 395–396;
43. S. D. Taylor, F. Mirzaei, A. Sharifi, S. L. Bearne, J. Org. Chem. 2006, 71, 9420–9430.
44. For selected examples, see:
45. M. S. Smyth, H. Ford, T. R. Burke, Tetrahedron Lett. 1992, 33, 4137–4140;
46. F. Benayoud, G. B. Hammond, Chem. Commun. 1996, 1447–1448;
47. D. Solas, R. L. Hale, D. V. Patel, J. Org. Chem. 1996, 61, 1537–1539.
48. For selected examples, see:
49. S. F. Martin, D. W. Dean, A. S. Wagman, Tetrahedron Lett. 1992, 33, 1839–1842;
50. D. B. Berkowitz, D. Bhuniya, G. Peris, Tetrahedron Lett. 1999, 40, 1869–1872;
51. D. B. Berkowitz, M. J. Eggen, Q. Shen, J. Org. Chem. 1993, 58, 6174–6176;
52. D. B. Berkowitz, M. J. Eggen, Q. Shen, J. Org. Chem. 1996, 61, 4666–4675.
53. For selected examples, see:
54. T. Delaunay, T. Poisson, P. Jubault, X. Pannecoucke, J. Fluorine Chem. 2015, 171, 56–59;
55. P. Cherkupally, P. Beier, J. Fluorine Chem. 2012, 137, 34–43;
56. G.-V. Röschenthaler, V. P. Kukhar, M. Y. Belik, K. I. Mazurenko, A. E. Sorochinsky, Tetrahedron 2006, 62, 9902–9910;
57. K. Blades, D. Lapôtre, J. M. Percy, Tetrahedron Lett. 1997, 38, 5895–5898;
58. T. Lequeux, J. M. Percy, Synlett 1995, 361–362;
59. M. Das, D. F. O'Shea, Chem. Eur. J. 2015, 21, 18717–18723;
60. M. D. Kosobokov, A. D. Dilman, M. I. Struchkova, P. A. Belyakov, J. Hu, J. Org. Chem. 2012, 77, 2080–2086;
61. M. Obayashi, K. Kondo, Tetrahedron Lett. 1982, 23, 2327–2328;
62. see references [15c] and [16c]
63. For selected examples, see:
64. S. Murakami, H. Ishii, T. Tajima, T. Fuchigami, Tetrahedron 2006, 62, 3761–3769;
65. C. De Schutter, E. Pfund, T. Lequeux, Tetrahedron 2013, 69, 5920–5926;
66. Z. Y. Yang, D. J. Burton, Tetrahedron Lett. 1991, 32, 1019–1022;
67. S. Pignard, C. Lopin, G. Gouhier, S. R. Piettre, J. Org. Chem. 2006, 71, 31–37;
68. S. R. Piettre, Tetrahedron Lett. 1996, 37, 2233–2236;
69. R. N. Haszeldine, D. L. Hobson, D. R. Taylor, J. Fluorine Chem. 1976, 8, 115–124;
70. T. F. Herpin, J. S. Houlton, W. B. Motherwell, B. P. Roberts, J.-M. Weibel, Chem. Commun. 1996, 613–614;
71. T. F. Herpin, W. B. Motherwell, B. P. Roberts, S. Roland, Tetrahedron 1997, 53, 15085–15100.
72. C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev. 2013, 113, 5322–5363;
73. J. M. R. Narayanam, C. R. J. Stephenson, Chem. Soc. Rev. 2010, 39, 102–113;
74. D. M. Schultz, T. P. Yoon, Science 2014, 343, 1239176.
75. L. Wang, X.-J. Wei, W.-L. Lei, H. Chen, L.-Z. Wu, Q. Liu, Chem. Commun. 2014, 50, 15916–15919.
76. S. Wang, W.-L. Jia, L. Wang, Q. Liu, Eur. J. Org. Chem. 2015, 6817–6821.
77. M. Zhu, W. Fu, G. Zou, C. Xu, Z. Wang, J. Fluorine Chem. 2015, 180, 1–6.
78. J. Xie, T. Zhang, F. Chen, N. Mehrkens, F. Rominger, M. Rudolph, A. S. K. Hashmi, Angew. Chem. Int. Ed. 2016, 55, 2934–2938;
79. Angew. Chem. 2016, 128, 2987–2991.
80. Z. Feng, F. Chen, X. Zhang, Org. Lett. 2012, 14, 1938–1941.
81. Z. Feng, Y.-L. Xiao, X. Zhang, Org. Chem. Front. 2014, 1, 113–116.
82. Z. Feng, Q.-Q. Min, Y.-L. Xiao, B. Zhang, X. Zhang, Angew. Chem. Int. Ed. 2014, 53, 1669–1673;
83. Angew. Chem. 2014, 126, 1695–1699.
84. X. Jiang, L. Chu, F.-L. Qing, New J. Chem. 2013, 37, 1736–1741.
85. J.-W. Gu, X. Zhang, Org. Lett. 2015, 17, 5384–5387.
86. A. Bayle, C. Cocaud, C. Nicolas, O. R. Martin, T. Poisson, X. Pannecoucke, Eur. J. Org. Chem. 2015, 3787–3792.
87. 2H groups, see:
88. B. Bayarmagnai, C. Matheis, K. Jouvin, L. J. Gooßen, Angew. Chem. Int. Ed. 2015, 54, 5753–5756;
89. Angew. Chem. 2015, 127, 5845–5848;
90. G. Danoun, B. Bayarmagnai, M. F. Grünberg, L. J. Gooßen, Angew. Chem. Int. Ed. 2013, 52, 7972–7975;
91. Angew. Chem. 2013, 125, 8130–8133;
92. G. Danoun, B. Bayarmagnai, M. F. Gruenberg, L. J. Gooßen, Chem. Sci. 2014, 5, 1312–1316;
93. C. Matheis, K. Jouvin, L. J. Gooßen, Org. Lett. 2014, 16, 5984–5987.
94. M. V. Ivanova, A. Bayle, T. Besset, T. Poisson, X. Pannecoucke, Angew. Chem. Int. Ed. 2015, 54, 13406–13410;
95. Angew. Chem. 2015, 127, 13604–13608.
96. Z. Feng, Y. L. Xiao, X. Zhang, Org. Chem. Front. 2016, 3, 466–469.
97. T. Yokomatsu, K. Suemune, T. Murano, S. Shibuya, J. Org. Chem. 1996, 61, 7207–7211.
98. F. Zhang, Q.-Q. Min, X. Zhang, Synthesis 2015, 47, 2912–2923.
99. X. Jiang, L. Chu, F.-L. Qing, Org. Lett. 2012, 14, 2870–2873.
100. Q. Chen, J. Zhou, Y. Wang, C. Wang, X. Liu, Z. Xu, L. Lin, R. Wang, Org. Lett. 2015, 17, 4212–4215.
101. Z. Ye, K. E. Gettys, X. Shen, M. Dai, Org. Lett. 2015, 17, 6074–6077.