Copper-mediated fluoroalkylation of aryl iodides enables facile access to diverse fluorinated compounds: The important role of the (2-Pyridyl)sulfonyl group

Organic Letters

Volumn 14, Issue 23, 2012, Pages 6080-6083

  Zhao, Yanchuan ^a   Gao, Bing ^a   Ni, Chuanfa ^a   Hu, Jinbo ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84870950529     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3029737     Document Type: Article

References (42)

1. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
2. Fluorine in Medicinal Chemistry and Chemical Biology; Ojima, I., Ed.; Wiley: Chichester, 2009.
3. Bégué, J.-P.; Bonnet-Delpon, D. Bioorganic and Medicinal Chemistry of Fluorine; Wiley-VCH: Weinheim, 2008.
4. Uneyama, K. Organofluorine Chemistry; Blackwell: Oxford, 2006.
5. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
6. Schlosser, M. Angew. Chem., Int. Ed. 2006, 45, 5432
7. Meanwell, N. A. J. Med. Chem. 2011, 54, 2529
8. For a recent review, see: Tomashenko, Q. A.; Grushin, V. V. Chem. Rev. 2011, 111) 4475
9. Hu, J.; Zhang, W.; Wang, F. Chem. Commun. 2009, 7465 and references cited therein
10. Davis, C. R.; Burton, D. I. Fluorinated Organocopper Reagents. In The Chemistry of Organocopper Compounds; Rappoport, Z.; Marek, I., Eds.; Wiley: Chichester, 2009.
11. Zhu, J.; Zhang, W.; Zhang, L.; Liu, J.; Zheng, J.; Hu, J. J. Org. Chem. 2010, 75, 5505 and references cited therein
12. Fujikawa, K.; Fujioka, Y.; Kobayashi, A.; Amii, H. Org. Lett. 2011, 13, 5560
13. Fier, P. S.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 5524
14. Feng, Z.; Chen, F.; Zhang, X. Org. Lett. 2012, 14, 1938
15. Qi, Q.; Shen, Q.; Lu, L. J. Am. Chem. Soc. 2012, 134, 6548
16. Oishi, M.; Kondo, H.; Amii, H. Chem. Commun. 2009, 1909
17. Novak, P.; Lishchynskyi, A.; Grushin, V. V. J. Am. Chem. Soc. 2012, 134, 16167
18. Novak, P.; Lishchynskyi, A.; Grushin, V. V. Angew. Chem., Int. Ed. 2012, 51, 7767
19. Zhang, X.; Qiu, W. M.; Burton, D. J. Tetrahedron Lett. 1999, 40, 2681
20. Guo, C.; Wang, R.-W.; Guo, Y.; Qing, F.-L. J. Fluorine Chem. 2012, 133, 86
21. Guo, C.; Yue, X.; Qing, F.-L. Synthesis 2010, 1837
22. Guo, Y.; Twamley, B.; Shreeve, J. M. Org. Biol. Chem. 2009, 7, 1716
23. Beare, N. A.; Hartwig, J. F. J. Org. Chem. 2002, 67, 541
24. Dieter, R. K. N-Functionalized Organocuprates. In The Chemistry of Organocopper Compounds; Rappoport, Z.; Marek, I., Eds.; Wiley: Chichester, 2009, and references cited therein.
25. Zhao, Y.; Huang, W.; Zhu, L.; Hu, J. Org. Lett. 2010, 12, 1444
26. Zhao, Y.; Gao, B.; Hu, J. J. Am. Chem. Soc. 2012, 134, 5790
27. Prakash, G. K. S.; Ni, C.; Wang, F.; Hu, J.; Olah, G. A. Angew. Chem., Int. Ed. 2011, 50, 2559
28. Zhao, Y.; Zhang, L.; Xu, G.; Zheng, J.; Hu, J. Sci. Sin. Chim. 2011, 41, 1833
29. Knochel, P. Synlett 1995, 393
30. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
31. Garcia-Rubia, A.; Gomez Arrayas, R.; Carretero, J. C. Angew. Chem., Int. Ed. 2009, 48, 6511
32. García-Rubia, A.; Urones, B.; Gómez Arrayás, R.; Carretero, J. C. Chem.î-̧Eur. J. 2010, 16, 9676
33. García-Rubia, A.; Fernández-Ibáñez, M. Á.; Gómez Arrayás, R.; Carretero, J. C. Chem.î-̧Eur. J. 2011, 17, 3567
34. Llamas, T.; Gomez Arrayas, R.; Carretero, J. C. Angew. Chem., Int. Ed. 2007, 46, 3329
35. Esquivias, J.; Gomez Arrayas, R.; Carlos Carretero, J. Angew. Chem., Int. Ed. 2007, 46, 9257
36. Wnuk, S. F.; Robins, M. J. J. Am. Chem. Soc. 1996, 118, 2519
37. Wnuk, S. F.; Rios, J. M.; Khan, J.; Hsu, Y. L. J. Org. Chem. 2000, 65, 4169
38. Aïssa, C. J. Org. Chem. 2005, 71, 360
39. Giesbrecht, H. E.; Knight, B. J.; Tanguileg, N. R.; Emerson, C. R.; Blakemore, P. R. Synlett 2010, 374
40. Olah, G. A.; Prakash, G. K. S.; Sommer, J.; Molnar, A. Superacid Chemistry, 2 nd ed.; Wiley: New York, 2009.
41. Lawrence, R. M.; Biller, S. A.; Dickson, J. K.; Logan, J. V. H.; Magnin, D. R.; Sulsky, R. B.; DiMarco, J. D.; Gougoutas, J. Z. B.; Beyer, D.; Kunselman, S.; Taylor, C.; Lan, S.-J.; Ciosek, C. P.; Harrity, T. W.; Jolibois, K. G.; Slusarchyk, L. K. D. A. J. Am. Chem. Soc. 1996, 118, 11668
42. Enders, D.; Saeidian, H.; Mirjafary, Z.; Iffland, D.; Raabe, G.; Rusink, J. Synlett 2009, 2872 and references cited therein