Pd-catalyzed direct arylation of polyfluoroarenes on water under mild conditions using PPh 3 ligand

Journal of Organic Chemistry

Volumn 77, Issue 6, 2012, Pages 2992-2998

  Chen, Fei ^a   Min, Qiao Qiao ^a   Zhang, Xingang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL IODIDES; ARYLATIONS; C-H BOND; FUNCTIONALIZATIONS; FUNCTIONALIZED; MILD REACTION CONDITIONS; PURE WATER; REACTION EFFICIENCY; REACTION MEDIUM;

AROMATIC COMPOUNDS; FUNCTIONAL GROUPS; LIGANDS;

CATALYSIS;

IODIDE; LIGAND; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POLYFLUOROARENE DERIVATIVE; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG; WATER;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; REACTION ANALYSIS; SYNTHESIS;

EID: 84863337693     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300036d     Document Type: Article

References (48)

1. Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210
2. Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
3. Babudri, F.; Farinola, G. M.; Naso, F.; Ragni, R. Chem. Commun. 2007, 1003
4. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
5. Amii, H.; Uneyama, K. Chem. Rev. 2009, 109, 2119
6. Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754
7. Lafrance, M.; Shore, D.; Fagnou, K. Org. Lett. 2006, 8, 5097
8. Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 1128
9. Do, H.-Q.; Khan, R. M. K.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 15185
10. He, C.-Y.; Fan, S.; Zhang, X. J. Am. Chem. Soc. 2010, 132, 12850
11. Wei, Y.; Kan, J.; Wang, M.; Su, W.; Hong, M. Org. Lett. 2009, 11, 3346
12. Wei, Y.; Su, W. J. Am. Chem. Soc. 2010, 132, 16377
13. Li, H.; Liu, J.; Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Org. Lett. 2011, 13, 276
14. Campeau, L.-C.; Fagnou, K. Chem. Commun. 2006, 1253
15. Daugulis, O.; Zaitzev, V. G.; Shabashov, D.; Pham, Q.-N.; Lazareva, A. Synlett 2006, 3382
16. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174
17. Giri, R.; Shi, B. F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242
18. Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem., Int. Ed. 2009, 48, 9792
19. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624
20. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147
21. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677
22. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
23. Li, C.-J.; Chen, L. Chem. Soc. Rev. 2006, 35, 68
24. Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725
25. Butler, R. N.; Coyne, A. G. Chem. Rev. 2010, 110, 6302
26. Turner, G. L.; Morris, J. A.; Greaney, M. F. Angew. Chem., Int. Ed. 2007, 46, 7996
27. Flegeau, E. F.; Popkin, M. E.; Greaney, M. F. Org. Lett. 2008, 10, 2717
28. Ohnmacht, S. A.; Patrizia, M.; Culshaw, A. J.; Greaney, M. F. Chem. Commun. 2008, 10, 1241
29. Ohnmacht, S. A.; Culshaw, A. J.; Greaney, M. F. Org. Lett. 2010, 12, 224
30. Nishikata, T.; Abela, A. R.; Lipshutz, B. H. Angew. Chem., Int. Ed. 2010, 49, 781
31. A Pd-catalyzed direct arylation of polyfluoroarenes at room temperature using expensive electron-rich bulky phosphine ligand in a water mixed solvent system (EtOAc/water = 2.5:1) has been reported recently; see: René, O.; Fagnou, K. Org. Lett. 2010, 12, 2116
32. Zhang, X.; Fan, S.; He, C.-Y.; Wan, X.; Min, Q.-Q.; Yang, J.; Jiang, Z.-X. J. Am. Chem. Soc. 2010, 132, 4506
33. Fan, S.; Chen, F.; Zhang, X. Angew. Chem., Int. Ed. 2011, 50, 5918
34. Fan, S.; Yang, J.; Zhang, X. Org. Lett. 2011, 13, 4374
35. Fan, S.; He, C.-Y.; Zhang, X. Chem. Commun. 2010, 46, 4926
36. Chen, F.; Zhang, X. Chem. Lett. 2011, 40, 978
37. He, C.-Y.; Min, Q.-Q.; Zhang, X. Organometallics 2012, 10.1021/om200873j
38. Grove, D. M.; van Koten, G.; Louwen, J. N.; Noltes, J. G.; Spec, A. L. J. Am. Chem. Soc. 1982, 104, 6609
39. Liston, D. J.; Lee, Y. J.; Scheidt, W. R.; Reed, C. A. J. Am. Chem. Soc. 1989, 111, 6643
40. Denmark, S. E.; Schnute, M. E. J. Org. Chem. 1995, 60, 1013
41. Albano, V. G.; Di Serio, M.; Monari, M.; Orabona, I.; Panunzi, A.; Ruffo, F. Inorg. Chem. 2002, 41, 2672
42. Zahn, A.; Brotschi, C.; Leumann, C. J. Chem.-Eur. J. 2005, 11, 2125
43. Guo, P.; Joo, J. M.; Rakshit, S.; Sames, D. J. Am. Chem. Soc. 2011, 133, 16338
44. For a review, see: Lapointe, D.; Fagnou, K. Chem. Lett. 2010, 39, 1118
45. Shang, R.; Fu, Y.; Wang, Y.; Xu, Q.; Yu, H.-Z.; Liu, L. Angew. Chem., Int. Ed. 2009, 48, 9350
46. Birchall, J. M.; Evans, L. R.; Haszeldine, R. N. J. Chem. Soc., Perkin Trans. 1 1974, 1715
47. Korenaga, T.; Kosaki, T.; Fukumura, R.; Ema, T.; Sakai, T. Org. Lett. 2005, 7, 4915
48. Schaub, T; Backes, M; Radius, U. J. Am. Chem. Soc. 2006, 128, 15964