An Electrophilic Reagent for the Direct Introduction of the SCF2PO(OEt)2Group to Molecules

Angewandte Chemie - International Edition

Volumn 55, Issue 43, 2016, Pages 13490-13494

  Xiong, Heng Ying ^a   Bayle, Alexandre ^a   Pannecoucke, Xavier ^a   Besset, Tatiana ^a  

^a UNIVERSITÉ DE ROUEN   (France)

Author keywords

difluoromethylthiolation; electrophilic reagents; fluorine; sulfur; synthetic methods

Indexed keywords

CHEMICAL ENGINEERING; CHEMICAL REACTIONS; CHEMISTRY; FLUORINE; SULFUR;

2-GROUP; ANTI-INFLAMMATORIES; DIFLUOROMETHYLTHIOLATION; ELECTROPHILIC REAGENTS; METAL-FREE CONDITIONS; SYNTHETIC METHODS;

REAGENTS;

EID: 84991217062     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201607231     Document Type: Article

References (87)

1. J. Wang, M. Sánchez-Roselló, J. L. Aceña, C. del Pozo, A. E. Sorochinsky, S. Fustero, V. A. Soloshonok, H. Liu, Chem. Rev. 2014, 114, 2432–2506;
2. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320–330;
3. E. A. Ilardi, E. Vitaku, J. T. Njardarson, J. Med. Chem. 2014, 57, 2832–2842;
4. E. P. Gillis, K. J. Eastman, M. D. Hill, D. J. Donnelly, N. A. Meanwell, J. Med. Chem. 2015, 58, 8315–8359.
5. X.-H. Xu, K. Matsuzaki, N. Shibata, Chem. Rev. 2015, 115, 731–764, and references therein;
6. C. Ni, M. Hu, J. Hu, Chem. Rev. 2015, 115, 765–825;
7. M.-C. Belhomme, T. Besset, T. Poisson, X. Pannecoucke, Chem. Eur. J. 2015, 21, 12836–12865;
8. C. Ni, L. Zhu, J. Hu, Acta Chim. Sin. 2015, 73, 90–115;
9. T. Besset, T. Poisson, X. Pannecoucke, Eur. J. Org. Chem. 2015, 2765–2789;
10. T. Besset, T. Poisson, X. Pannecoucke, Chem. Eur. J. 2014, 20, 16830–16845;
11. H. Egami, M. Sodeoka, Angew. Chem. Int. Ed. 2014, 53, 8294–8308;
12. Angew. Chem. 2014, 126, 8434–8449;
13. T. Liang, C. N. Neumann, T. Ritter, Angew. Chem. Int. Ed. 2013, 52, 8214–8264;
14. Angew. Chem. 2013, 125, 8372–8423;
15. G. Landelle, A. Panossian, S. Pazenok, J.-P. Vors, F. R. Leroux, Beilstein J. Org. Chem. 2013, 9, 2476–2536;
16. T. Furuya, A. S. Kamlet, T. Ritter, Nature 2011, 473, 470–477;
17. B. Manteau, S. Pazenok, J. P. Vors, F. R. Leroux, J. Fluorine Chem. 2010, 131, 140–158;
18. T. Besset, P. Jubault, X. Pannecoucke, T. Poisson, Org. Chem. Front. 2016, 3, 1004–1010.
19. D. O'Hagan, Chem. Soc. Rev. 2008, 37, 308–319;
20. D. O'Hagan, H. S. Rzepa, Chem. Commun. 1997, 645–652;
21. K. Uneyama, Organofluorine Chemistry, Blackwell Publishing Ltd., Oxford, 2006.
22. For selected reviews, see:
23. F. Toulgoat, S. Alazet, T. Billard, Eur. J. Org. Chem. 2014, 2415–2428;
24. S. Barata-Vallejo, S. Bonesi, A. Postigo, Org. Biomol. Chem. 2016, 14, 7150–7182; for selected examples, see:
25. S. Alazet, L. Zimmer, T. Billard, Chem. Eur. J. 2014, 20, 8589–8593;
26. B. Exner, B. Bayarmagnai, F. Jia, L. J. Gooßen, Chem. Eur. J. 2015, 21, 17220–17223;
27. M. Hu, J. Rong, W. Miao, C. Ni, Y. Han, J. Hu, Org. Lett. 2014, 16, 2030–2033;
28. F. Hu, X.-X. Shao, D.-H. Zu, L. Lu, Q. Shen, Angew. Chem. Int. Ed. 2014, 53, 6105–6109;
29. Angew. Chem. 2014, 126, 6219–6223;
30. J.-B. Liu, X.-H. Xu, Z.-H. Chen, F.-L. Qing, Angew. Chem. Int. Ed. 2015, 54, 897–900;
31. Angew. Chem. 2015, 127, 911–914;
32. T. Yang, L. Lu, Q. Shen, Chem. Commun. 2015, 51, 5479–5481;
33. H.-Y. Xiong, T. Besset, D. Cahard, X. Pannecoucke, J. Org. Chem. 2015, 80, 4204–4212;
34. K.-Y. Ye, X. Zhang, L.-X. Dai, S.-L. You, J. Org. Chem. 2014, 79, 12106–12110;
35. Z. Huang, Y.-D. Yang, E. Tokunaga, N. Shibata, Org. Lett. 2015, 17, 1063–1065;
36. K. Zhang, J.-B. Liu, F.-L. Qing, Chem. Commun. 2014, 50, 14157–14160;
37. R. Pluta, P. Nikolaienko, M. Rueping, Angew. Chem. Int. Ed. 2014, 53, 1650–1653;
38. Angew. Chem. 2014, 126, 1676–1679;
39. L. Jiang, J. Qian, W. Yi, G. Lu, C. Cai, W. Zhang, Angew. Chem. Int. Ed. 2015, 54, 14965–14969;
40. Angew. Chem. 2015, 127, 15178–15182;
41. Y. Yang, L. Xu, S. Yu, X. Liu, Y. Zhang, D. A. Vicic, Chem. Eur. J. 2016, 22, 858–863;
42. Q. Wang, Z. Qi, F. Xie, X. Li, Adv. Synth. Catal. 2015, 357, 355–360.
43. B. Bayarmagnai, C. Matheis, K. Jouvin, L. J. Gooßen, Angew. Chem. Int. Ed. 2015, 54, 5753–5756;
44. Angew. Chem. 2015, 127, 5845–5848;
45. K. Jouvin, C. Matheis, L. J. Gooßen, Chem. Eur. J. 2015, 21, 14324–14327;
46. J. Wu, Y. Gu, X. Leng, Q. Shen, Angew. Chem. Int. Ed. 2015, 54, 7648–7652;
47. Angew. Chem. 2015, 127, 7758–7762;
48. J. Wu, Y. Liu, C. Lu, Q. Shen, Chem. Sci. 2016, 7, 3757–3762;
49. D. Zhu, Y. Gu, L. Lu, Q. Shen, J. Am. Chem. Soc. 2015, 137, 10547–10553;
50. S. Arimori, O. Matsubara, M. Takada, M. Shiro, N. Shibata, R. Soc. Open Sci. 2016, 3, 160102.
51. W. Zhang, J. Zhu, J. Hu, Tetrahedron Lett. 2008, 49, 5006–5008.
52. C. Matheis, B. Bayarmagnai, K. Jouvin, L. J. Gooßen, Org. Chem. Front. 2016, 3, 949–952.
53. For selected examples, see
54. Q. Glenadel, M. Bordy, S. Alazet, A. Tlili, T. Billard, Asian J. Org. Chem. 2016, 5, 428–433;
55. F. Baert, J. Colomb, T. Billard, Angew. Chem. Int. Ed. 2012, 51, 10382–10385;
56. Angew. Chem. 2012, 124, 10528–10531;
57. A. Tlili, S. Alazet, Q. Glenadel, T. Billard, Chem. Eur. J. 2016, 22, 10230–10234;
58. E. Ismalaj, D. Le Bars, T. Billard, Angew. Chem. Int. Ed. 2016, 55, 4790–4793;
59. Angew. Chem. 2016, 128, 4868–4871.
60. J.-B. Han, H.-L. Qin, S.-H. Ye, L. Zhi, C.-P. Zhang, J. Org. Chem. 2016, 81, 2506–2512;
61. Y.-M. Lin, W.-B. Yi, W.-Z. Shen, G.-P. Lu, Org. Lett. 2016, 18, 592–595.
62. For selected reviews, see:
63. A. R. Murphy, J. M. J. Fréchet, Chem. Rev. 2007, 107, 1066–1096;
64. C. Shen, P. Zhang, Q. Sun, S. Bai, T. S. A. Hor, X. Liu, Chem. Soc. Rev. 2015, 44, 291–314;
65. M. V. Ivanova, A. Bayle, T. Besset, X. Pannecoucke, T. Poisson, Chem. Eur. J. 2016, 22, 10284–10293, and references therein.
66. A. Konno, T. Fuchigami, J. Org. Chem. 1997, 62, 8579–8581;
67. T. Lequeux, F. Lebouc, C. Lopin, H. Yang, G. Gouhier, S. R. Piettre, Org. Lett. 2001, 3, 185–188;
68. A. Henry-dit-Quesnel, L. Toupet, J.-C. Pommelet, T. Lequeux, Org. Biomol. Chem. 2003, 1, 2486–2491;
69. L. Aliouane, S. Chao, L. Brizuela, E. Pfund, O. Cuvillier, L. Jean, P.-Y. Renard, T. Lequeux, Bioorg. Med. Chem. 2014, 22, 4955–4960;
70. C. De Schutter, E. Pfund, T. Lequeux, Tetrahedron 2013, 69, 5920–5926.
71. G. Danoun, B. Bayarmagnai, M. F. Grünberg, L. J. Gooßen, Chem. Sci. 2014, 5, 1312–1316.
72. H.-Y. Xiong, X. Pannecoucke, T. Besset, Org. Chem. Front. 2016, 3, 620–624.
73. See the Supporting Information for further details.
74. M. V. Ivanova, A. Bayle, T. Besset, T. Poisson, X. Pannecoucke, Angew. Chem. Int. Ed. 2015, 54, 13406–13410;
75. Angew. Chem. 2015, 127, 13604–13608;
76. A. Bayle, C. Cocaud, C. Nicolas, O. R. Martin, T. Poisson, X. Pannecoucke, Eur. J. Org. Chem. 2015, 3787–3792.
77. The reagent 2 can be stored for three months at room temperature under air without any loss of efficiency (see the Supporting Information).
78. CCDC 1494845 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
79. W. Wu, X. Zhang, F. Liang, S. Cao, Org. Biomol. Chem. 2015, 13, 6992–6999.
80. L. Craine, M. Raban, Chem. Rev. 1989, 89, 689–712.
81. 2, TMSCl in replacement of TFA.
82. P. Beier, A. V. Alexandrova, M. Zibinsky, G. K. S. Prakash, Tetrahedron 2008, 64, 10977–10985.
83. R. A. Scherrer, M. W. Whitehouse, Antiinflammatory agents: Chemistry and Pharmacology, Vol. 2, Academic Press, New York, 1974;
84. R. L. Vigdahl, R. H. Tukey, Biochem. Pharmacol. 1977, 26, 307–311.
85. J. K. Harrington, J. E. Robertson, D. C. Kvam, R. R. Hamilton, K. T. McGurran, R. J. Trancik, K. F. Swingle, G. G. I. Moore, J. F. Gerster, J. Med. Chem. 1970, 13, 137;
86. V. V. Farrar, J. Chem. Soc. 1960, 3058–3062.
87. X. J. Tang, C. S. Thomoson, W. R. Dolbier, Jr., Org. Lett. 2014, 16, 4594–4597.