Transformation of anionically activated trifluoromethyl groups to heterocycles under mild aqueous conditions

Organic Letters

Volumn 13, Issue 7, 2011, Pages 1804-1807

  Qiao, Jennifer X ^a   Wang, Tammy C ^a   Hu, Carol ^a   Li, Jianqing ^a   Wexler, Ruth R ^a   Lam, Patrick Y S ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; FLUORINE DERIVATIVE; HETEROCYCLIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METHYLATION; STEREOISOMERISM;

ANIONS; FLUORINE COMPOUNDS; HETEROCYCLIC COMPOUNDS; METHYLATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79953165036     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200326u     Document Type: Article

References (36)

1. Boehm, H.; Banner, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Mueller, K.; Obst-Sander, U.; Stahl, M. ChemBioChem 2004, 5, 637-643
2. Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2005, 44, 214-231
3. Schlosser, M. Angew. Chem., Int. Ed. 2006, 45, 5432-5446
4. Ma, J.-A.; Cahard, D. J. Fluorine Chem. 2007, 128, 975-996
5. Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886
6. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330
7. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359-4369
8. Chu, L.; Qing, F.-L. Org. Lett. 2010, 12, 5060-5063 and refrences cited therein
9. For a recent review on Chan-Lam coupling, see: Qiao, J. X.; Lam, P. Y. S. Synthesis 2011, 829 - 856.
10. Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679-1681 and references cited therein
11. Jones, R. G. J. Am. Chem. Soc. 1947, 69, 2346-2350
12. Belcher, R.; Stacey, M.; Sykes, A.; Tatlow, J. C. J. Chem. Soc. 1954, 3846-3851
13. O'Mahony, G.; Pitts, A. K. Org. Lett. 2010, 12, 2024-2027
14. Wydra, R. L.; Patterson, S. E.; Strekowski, L. J. Heterocycl. Chem. 1990, 23, 803-805
15. Kiselyov, A. S.; Hojjat, M.; Van Aken, K.; Strekowski, L. Heterocycles 1994, 37, 775-782
16. Kiselyov, A. S.; Strekowski, L. Org. Prep. Proced. Int. 1996, 3, 289-318 and references cited therein
17. Strekowski, L.; Lin, S.; Nguyen, J.; Redmore, N. P.; Mason, J. C.; Kiselyov, A. S. Heterocycl. Commun. 1995, 5-6, 331-334
18. Kobayashi, Y.; Kumadaki, I. Acc. Chem. Res. 1978, 5, 197-204
19. Detailed chemistry and SAR results will be disclosed in due course.
20. Betley, J. R.; Cesaro-Tadic, S.; Mekhalfia, A.; Rickard, J. H.; Denham, H.; Partridge, L. J.; Pluckthun, A.; Blackburn, G. M. Angew. Chem., Int. Ed. 2002, 5, 775-777
21. Examples of recent developments in the synthesis of C-C linked aryl-heterocycles and heteroaryl-heterocycles: Sardarian, A. R.; Shahsavari-Fard, Z. Synlett 2008, 1391-1393
22. Moghaddam, F. M.; Bardajee, G. R.; Ismaili, H.; Taimoory, S. M. D. Synth. Commun. 2006, 36, 2543-2548
23. Ma, D.; Xue, P.; Jiang, Y.; Xie, S.; Zhang, X.; Dong, J. Angew. Chem., Int. Ed. 2009, 48, 4222-4225
24. Mukhopadhyay, C.; Datta, A. Heterocycles 2007, 71, 1837-1842
25. Bahrami, K.; Khodaei, M. M.; Naali, F. J. Org. Chem. 2008, 73, 6835-6837
26. Bahrami, K.; Khodaei, M. M.; Naali, F. Synlett 2009, 569-572
27. Bertani, B.; Cardullo, F.; Dambruoso, P.; Marzorati, P.; Micheli, F.; Pasquarello, A.; Seri, C.; Tedesco, G. WO2009/043883 A1.
28. Samota, M. K.; Seth, G. Heteroat. Chem. 2010, 21, 44-50
29. Malmstrom, J.; Pyring., D.; Slivo, C.; Sohn, D.; Swahn, B.-M.; Wensbo, D. WO2007/149030 A1.
30. Heraclio, L.-R.; Horacio, B.-O.; Susana, R.-L.; Rosa, S.; Norberto, F. Tetrahedron Lett. 2010, 51, 2633-2635
31. Button, K. M.; Gossage, R. A. J. Heterocycl. Chem. 2003, 40, 513-517
32. Johnson., S. M.; Connelly, S.; Wilson, I. A.; Kelly, J. W. J. Med. Chem. 2008, 51, 260-270
33. Chakrabarty, M.; Mukherji, A.; Mukherjee, R.; Arima, S.; Harigaya, Y. Tetrahedron Lett. 2007, 48, 5239-5242
34. Lin, S.-Y.; Isome, Y.; Stewart, E.; Liu, J.-F.; Yohannes, D.; Yu, L. Tetrahedron Lett. 2006, 47, 2883-2886
35. Peterson, T.; Falk, K.-E.; Leong, S. A.; Klein, M. P.; Neilands, J. B. J. Am. Chem. Soc. 1980, 102, 7715-7718
36. Curtis, M. P.; Sammons, M. F.; Piotrowski, D. W. Tetrahedron Lett. 2009, 50, 5479-5481