Silver-mediated methoxycarbonyltetrafluoroethylation of arenes

Organic Letters

Volumn 15, Issue 13, 2013, Pages 3468-3471

  Hafner, Andreas ^a   Feuerstein, Thomas J ^a   Bräse, Stefan ^a,b  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

^b KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; FLUORINATED HYDROCARBON; SILVER;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HALOGENATION; STEREOISOMERISM;

ALKENES; ALKYLATION; CATALYSIS; HALOGENATION; HYDROCARBONS, FLUORINATED; MOLECULAR STRUCTURE; SILVER; STEREOISOMERISM;

EID: 84879998898     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401558z     Document Type: Article

References (64)

1. Kirsch, P. Modern Fluoroorganic Chemistry; Wiley-VCH: Weinheim, Germany, 2004.
2. Filler, R.; Kobayashi, Y.; Yagupolskii, Y. L. Organofluorine Compounds in Medicinal Chemistry and Biological Applications; Elsevier: Amsterdam, 1993.
3. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
4. Zhang, L.-S.; Chen, K.; Chen, G.; Li, B.-J.; Luo, S.; Guo, Q.-Y.; Wei, J.-B.; Shi, Z.-J. Org. Lett. 2013, 15, 10
5. Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2012, 134, 1298
6. Zhang, X.-G.; Dai, H.-X.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2012, 134, 11948
7. Hafner, A.; Bräse, S. Adv. Synth. Catal. 2013, 355, 996
8. Review: Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475
9. Xu, J.; Xiao, B.; Xie, C.-Q.; Luo, D.-F.; Liu, L.; Fu, Y. Angew. Chem., Int. Ed. 2012, 51, 12551
10. Hu, M.; Ni, C.; Hu, J. J. Am. Chem. Soc. 2012, 134, 15257
11. Li, Y.; Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8221
12. Chu, L.; Qing, F.-L. Org. Lett. 2012, 14, 2106
13. Parsons, A. T.; Senecal, T. D.; Buchwald, S. L. Angew. Chem., Int. Ed. 2012, 51, 2947
14. Cho, E. J.; Buchwald, S. L. Org. Lett. 2011, 13, 6552
15. Hafner, A.; Bräse, S. Adv. Synth. Catal. 2011, 353, 3044
16. Zhao, T. S. N.; Szabo, K. J. Org. Lett. 2012, 14, 3966
17. Janson, P. G.; Ghoneim, I.; Ilchenko, N. O.; Szabo, K. J. Org. Lett. 2012, 14, 2882
18. Kawai, H.; Furukawa, T.; Nomura, Y.; Tokunaga, E.; Shibata, N. Org. Lett. 2011, 13, 3596
19. Wu, X.; Chu, L.; Qing, F. L. Angew. Chem., Int. Ed. 2013, 52, 2198
20. Tomashenko, O. A.; Escudero-Adán, E. C.; Martínez Belmonte, M.; Grushin, V. V. Angew. Chem., Int. Ed. 2011, 50, 7655
21. Weng, Z.; Lee, R.; Jia, W.; Yuan, Y.; Wang, W.; Feng, X.; Huang, K.-W. Organometallics 2011, 30, 3229
22. Kondo, H.; Oishi, M.; Fujikawa, K.; Amii, H. Adv. Synth. Catal. 2011, 353, 1247
23. Morimoto, H.; Tsubogo, T.; Litvinas, N. D.; Hartwig, J. F. Angew. Chem., Int. Ed. 2011, 50, 3793
24. Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679
25. Oishi, M.; Kondo, H.; Amii, H. Chem. Commun. 2009, 1909
26. Novák, P.; Lishchynskyi, A.; Grushin, V. V. Angew. Chem., Int. Ed. 2012, 51, 7767
27. Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034
28. Khan, B. A.; Buba, A. E.; Goossen, L. J. Chem.-Eur. J. 2012, 18, 1577
29. Li, Y.; Wu, L.; Neumann, H.; Beller, M. Chem. Commun. 2013, 49, 2628
30. Litvinas, N. D.; Fier, P. S.; Hartwig, J. F. Angew. Chem., Int. Ed. 2011, 51, 536
31. Knauber, T.; Arikan, F.; Röschenthaler, G.-V.; Goossen, L. J. Chem.-Eur. J. 2011, 17, 2689
32. Wu, X.; Chu, L.; Qing, F.-L. Tetrahedron Lett. 2013, 54, 249
33. Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224
34. Ji, Y.; Brueckl, T.; Baxter, R. D.; Fujiwara, Y.; Seiple, I. B.; Su, S.; Blackmond, D. G.; Baran, P. S. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 14411
35. Review: Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8950
36. Hafner, A.; Bräse, S. Angew. Chem., Int. Ed. 2012, 51, 3713
37. Miller, W. T., Jr.; Burnard, R. J. J. Am. Chem. Soc. 1968, 90, 7367
38. Burch, R. R.; Calabrese, J. C. J. Am. Chem. Soc. 1986, 108, 5359
39. Dyatkin, B.; Martynov, B.; Martynova, L.; Kizim, N.; Sterlin, S.; Stumbrevichute, Z.; Fedorov, L. J. Organomet. Chem. 1973, 57, 423
40. Naumann, D.; Wessel, W.; Hahn, J.; Tyrra, W. J. Organomet. Chem. 1997, 547, 79
41. Review: Tyrra, W.; Naumann, D. J. Fluorine Chem. 2004, 125, 823
42. Tyrra, W. E. J. Fluorine Chem. 2001, 112, 149
43. King, R. B.; Zipperer, W. C. Inorg. Chem. 1972, 11, 2119
44. Zeng, Y.; Zhang, L.; Zhao, Y.; Ni, C.; Zhao, J.; Hu, J. J. Am. Chem. Soc. 2013, 135, 2955
45. Kremlev, M. M.; Mushta, A. I.; Tyrra, W.; Naumann, D.; Fischer, H. T. M.; Yagupolskii, Y. L. J. Fluorine Chem. 2007, 128, 1385
46. Ye, Y.; Lee, S. H.; Sanford, M. S. Org. Lett. 2011, 13, 5464
47. Bartlett, P. D.; Wheland, R. C. J. Am. Chem. Soc. 1972, 94, 2145
48. Paleta, O.; Svoboda, J.; Dedek, V. J. Fluorine Chem. 1983, 23, 171
49. In fact, only few examples are known in which highly fluorinated olefins are used for the perfluoroalkylation of arenes. These examples are either nucleophilic aromatic substitution reactions (e.g., Chambers, R. D.; Jackson, J. A.; Musgrave, W. K. R.; Storey, R. A. J. Chem. Soc. (C) 1968, 2221
50. Ohashi, M.; Kambara, T.; Hatanaka, T.; Saijo, H.; Doi, R.; Ogoshi, S. J. Am. Chem. Soc. 2011, 133, 3256.)
51. Kimball, D. B.; Haley, M. M. Angew. Chem., Int. Ed. 2002, 41, 3338
52. Bräse, S. Acc. Chem. Res. 2004, 37, 805
53. Liu, C.-Y.; Knochel, P. Org. Lett. 2005, 7, 2543
54. Barbero, M.; Degani, I.; Diulgheroff, N.; Dughera, S.; Fochi, R. Synthesis 2001, 2180
55. Döbele, M.; Vanderheiden, S.; Jung, N.; Bräse, S. Angew. Chem., Int. Ed. 2010, 49, 5986
56. Liu, C.-Y.; Knochel, P. J. Org. Chem. 2007, 72, 7106-7115
57. Patrick, T. B.; Juehne, T.; Reeb, E.; Hennessy, D. Tetrahedron Lett. 2001, 42, 3553
58. Gross, M. L.; Blank, D. H.; Welch, W. M. J. Org. Chem. 1993, 58, 2104
59. Reingruber, R.; Vanderheiden, S.; Wagner, A.; Nieger, M.; Muller, T.; Es-Sayed, M.; Bräse, S. Eur. J. Org. Chem. 2008, 3314
60. Rieu, J.-P.; Boucherle, A.; Cousse, H.; Mouzin, G. Tetrahedron 1986, 42, 4095
61. Goj, O.; Kotila, S.; Haufe, G. Tetrahedron 1996, 52, 12761
62. Schlosser, M.; Michel, D.; Guo, Z.-W.; Sih, C. J. Tetrahedron 1996, 52, 8257
63. Rozen, S.; Hagooly, A.; Harduf, R. J. Org. Chem. 2001, 66, 7464
64. Ricci, G.; Ruzziconi, R. J. Org. Chem. 2005, 70, 611