Pd-catalyzed direct arylation of nitro(pentafluorosulfanyl)benzenes with aryl bromides

Organic Letters

Volumn 15, Issue 19, 2013, Pages 5004-5007

  Wang, Chao ^a   Yu, Yan Bo ^a   Fan, Shilu ^a   Zhang, Xingang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84885104783     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4023326     Document Type: Article

References (50)

1. Smart, B. E. J. Fluorine Chem. 2001, 109, 3
2. Maienfisch, P.; Hall, R. G. Chimia 2004, 58, 93
3. Special issue on "Fluorine in the Life Sciences": ChemBioChem 2004, 5, 557.
4. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
5. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
6. O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308
7. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359
8. Furuya, T.; Klein, J. E. M. N.; Ritter, T. Synthesis 2010, 1804
9. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475
10. Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470
11. Ye, Y.; Sanford, M. S. Synlett 2012, 2005
12. Besset, T.; Schneider, C.; Cahard, D. Angew. Chem., Int. Ed. 2012, 51, 5048
13. Qing, F.-L. Chin. J. Org. Chem. 2012, 32, 815
14. Wang, X.; Zhang, Y.; Wang, J. Sci. Sin.: Chim. 2012, 42, 1417
15. Kirsch, P. Modern Fluoroorganic Chemistry Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, Germany, 2004.
16. Verma, R.; Kirchmeier, R.; Shreeve, J. Advances in Inorganic Chemistry; Elsevier: Amsterdam, 1994; pp 125-169.
17. Lentz, D.; Seppelt, K. In Chemistry of Hypervalent Compounds; Akiba, K.-Y., Ed.; Wiley-VCH: New York, 1999; p 295.
18. Altomonte, S.; Zanda, M. J. Fluorine Chem. 2012, 143, 57
19. Kirsch, P.; Bremer, M. Angew. Chem., Int. Ed. 2000, 39, 4216
20. Welch, J. T.; Lim, D. S. Bioorg. Med. Chem. 2007, 15, 6659
21. Wipf, P.; Mo, T.; Geib, S.; Caridha, D.; Dow, G.; Gerena, L.; Roncal, N.; Milner, E. Org. Biomol. Chem. 2009, 7, 4163
22. Stump, B.; Eberle, C.; Schweizer, W. B.; Kaiser, M.; Brun, R.; Kraut-Siegel, R. L.; Lentz, D.; Diederich, F. ChemBioChem 2009, 10, 79
23. Roberts, H. L. J. Chem. Soc. 1962, 3183
24. Sheppard, W. A. J. Am. Chem. Soc. 1960, 82, 4751
25. Sheppard, W. A. J. Am. Chem. Soc. 1962, 84, 3064
26. Bowden, R. D.; Comina, P. J.; Greenhall, M. P.; Kariuki, B. M.; Loveday, A.; Philp, D. Tetrahedron 2000, 56, 3399
27. Chambers, R. D.; Spink, R. C. H. Chem. Commun. 1999, 883
28. Umemoto, T. WO 2008/118787, 2008.
29. Beier, P.; Pastyrikova, T.; Vida, N.; Iakobson, G. Org. Lett. 2011, 13, 1466
30. Beier, P.; Pastyrikova, T.; Iakobson, G. J. Org. Chem. 2011, 76, 4681
31. Frischmuth, A.; Unsinn, A.; Groll, K.; Stadtmuller, H.; Knochel, P. Chem.-Eur. J. 2012, 18, 10234
32. 5Cl is a gaseous and highly toxic reagent. See: Ait-Mohand, S.; Dolbier, W. D., Jr. Org. Lett. 2002, 4, 3013
33. Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754
34. Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 1128
35. Caron, L.; Campeau, L.-C.; Fagnou, K. Org. Lett. 2008, 10, 4533
36. Campeau, L.-C.; Rousseaux, S.; Fagnou, K. J. Am. Chem. Soc. 2005, 127, 18020
37. Zhang, X.; Fan, S.; He, C.-Y.; Wan, X.; Min, Q.-Q.; Yang, J.; Jiang, Z.-X. J. Am. Chem. Soc. 2010, 132, 4506
38. He, C.-Y.; Fan, S.; Zhang, X. J. Am. Chem. Soc. 2010, 132, 12850
39. Fan, S.; Chen, F.; Zhang, X. Angew. Chem., Int. Ed. 2011, 50, 5918
40. Fan, S.; Yang, J.; Zhang, X. Org. Lett. 2011, 13, 4374
41. Fan, S.; He, C.-Y.; Zhang, X. Chem. Commun. 2010, 46, 4926
42. Chen, F.; Feng, Z.; He, C.-Y.; Wang, H.-Y.; Guo, Y.-l.; Zhang, X. Org. Lett. 2012, 14, 1176
43. Chen, F.; Min, Q.-Q.; Zhang, X. J. Org. Chem. 2012, 77, 2992
44. He, C.-Y.; Min, Q.-Q.; Zhang, X. Organometallics 2012, 31, 1335
45. Yu, Y.-B.; Fan, S.; Zhang, X. Chem.-Eur. J. 2012, 18, 14643
46. Davies, D. L.; Donald, S. M. A.; Macgregor, S. A. J. Am. Chem. Soc. 2005, 127, 13754
47. Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496
48. Garcia-Cuadrado, D.; de Mendoza, P.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2007, 129, 6880
49. Lafrance, M.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 14570
50. Welch, J. T.; Lim, D. S. Bioorg. Med. Chem. 2007, 15, 6659