Oxidative para- Triflation of acetanilides

Organic Letters

Volumn 15, Issue 7, 2013, Pages 1764-1767

  Pialat, Amélie ^a   Liégault, Benoît ^a   Taillefer, Marc ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84875942908     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400604e     Document Type: Article

References (42)

1. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067
2. Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1470
3. Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: New York, 2004.
4. Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85-126
5. Ritter, K. Synthesis 1993, 735-762
6. Ikawa, T.; Barder, T. E.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 13001-13007
7. Espino, G.; Kurbangalieva, A.; Brown, J. M. Chem. Commun. 2007, 1742-1744 and references therein
8. For a representative example where only aryltriflates (as opposed to other aryl (pseudo)halides) are efficient coupling partners, see: Watson, D. A.; Su, M.; Teverovskiy, G.; Zhang, Y.; García-Fortanet, J.; Kinzel, T.; Buchwald, S. L. Science 2009, 325, 1661-1664
9. Bhunia, A.; Yetra, A. R.; Biju, A. T. Chem. Soc. Rev. 2012, 41, 3140-3152
10. Tadross, P. M.; Stoltz, B. M. Chem. Rev. 2012, 112, 3550-3577
11. Dubrovskiy, A. V.; Markina, N. A.; Larock, R. C. Org. Biomol. Chem. 2013, 11, 191-218
12. Moriconi, A.; Bigogno, C.; Bianchini, G.; Caligiuri, A.; Resconi, A.; Dondio, M. G.; D'Anniballe, G.; Allegretti, M. ACS Med. Chem. Lett. 2011, 2, 768-773
13. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299-6302
14. Baraznenok, I. L.; Nenajdenko, V. G.; Balenkova, E. S. Tetrahedron 2000, 56, 3077-3119
15. Frantz, D. E.; Weaver, D. G.; Carey, J. P.; Kress, M. H.; Dolling, U. H. Org. Lett. 2002, 4, 4717-4718
16. Bengtson, A.; Hallberg, A.; Larhed, M. Org. Lett. 2002, 4, 1231-1233
17. Quideau, S.; Pouységu, L.; Deffieux, D. Synlett 2008, 66, 467-495
18. Pouységu, L.; Deffieux, D.; Quideau, S. Tetrahedron 2010, 66, 2235-2261
19. Roche, S. P.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2011, 50, 4068-4093
20. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299-5358
21. Zhdankin, V. V. ARKIVOC 2009, 1-62
22. Itoh, N.; Sakamoto, T.; Miyazawa, E.; Kikugawa, Y. J. Org. Chem. 2002, 67, 7424-7428
23. Karade, N. N.; Tiwari, G. B.; Huple, D. B.; Siddiqui, T. A. J. J. Chem. Res. 2006, 366-368
24. Jean, A.; Cantat, J.; Bérard, D.; Bouchu, D.; Canesi, S. Org. Lett. 2007, 9, 2553-2556
25. Liu, H.; Wang, X.; Gu, Y. Org. Biomol. Chem. 2011, 9, 1614-1620
26. Samanta, R.; Lategahn, J.; Antonchick, A. P. Chem. Commun. 2012, 48, 3194-3196
27. Jacquemot, G.; Ménard, M.-A.; L'Homme, C.; Canesi, S. Chem. Sci. 2013, 4, 1287-1292
28. During the preparation of this manuscript, the para -fluorination of N -pivaloyl anilines was also reported; see: Tian, T.; Zhong, W.-H.; Meng, S.; Meng, X.-B.; Li, Z.-J. J. Org. Chem. 2013, 78, 728-732
29. 2 can activate BTI by means of coordination to the trifluoroacetoxy ligand; see: Dohi, T.; Ito, M.; Morimoto, K.; Iwata, M.; Kita, Y. Angew. Chem., Int. Ed. 2008, 47, 1301-1304
30. Brown, N.; Luo, D.; Velde, D. V.; Yang, S.; Brassfield, A.; Buszek, K. R. Tetrahedron Lett. 2009, 50, 63-65
31. For a review on the use of nonaflates in transition metal-catalyzed couplings, see: Högermeier, J.; Reissig, H.-U. Adv. Synth. Catal. 2009, 351, 2747-2763
32. Fors, B. P.; Buchwald, S. L. J. Am. Chem. Soc. 2009, 131, 12898-12899
33. Monzon, G.; Knochel, P. Synlett 2010, 304-308
34. Barluenga, J.; Florentino, L.; Aznar, F.; Valdés, C. Org. Lett. 2011, 13, 510-513
35. Ikawa, T.; Nishiyama, T.; Nosaki, T.; Takagi, A.; Akai, S. Org. Lett. 2011, 13, 1730-1733
36. Shekhar, S.; Dunn, T. B.; Kotecki, B. J.; Montavon, D. K.; Cullen, S. C. J. Org. Chem. 2011, 76, 4552-4563
37. Manabe, K.; Kimura, T. Org. Lett. 2013, 15, 374-377
38. Hashmi, A. S.; Hengst, T.; Lothschütz, C.; Rominger, F. Adv. Synth. Catal. 2010, 352, 1315-1337
39. Cho, S. H.; Yoon, J.; Chang, S. J. Am. Chem. Soc. 2011, 133, 5996-6005
40. Antonchick, A. P.; Samanta, R.; Kulikov, K.; Lategahn, J. Angew. Chem., Int. Ed. 2011, 50, 8605-8608
41. For a similar observation, see: Dohi, T.; Maruyama, A.; Takenaga, N.; Senami, K.; Minamitsuji, Y.; Fujioka, H.; Caemmerer, S. B.; Kita, Y. Angew. Chem., Int. Ed. 2008, 47, 3787-3790
42. + as a soft counterion was recently demonstrated in the trifluoromethylation-iodination of arynes; see: Zeng, Y.; Zhang, L.; Zhao, Y.; Ni, C.; Zhao, J.; Hu, J. J. Am. Chem. Soc. 2013, 135, 2955-2958