Fluoroanalogs of DDT: Superacidic BF 3-H 2O catalyzed facile synthesis of 1,1,1-trifluoro-2,2-diarylethanes and 1,1-difluoro-2,2- diarylethanes

Organic Letters

Volumn 13, Issue 15, 2011, Pages 4128-4131

  Prakash, G K Surya ^a   Paknia, Farzaneh ^a   Mathew, Thomas ^a   Mlostoń, Gzregorz ^a,b   Joschek, Jens P ^a   Olah, George A ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b UNIVERSITY OF LODZ   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; BORON TRIFLUORIDE; CHLORPHENOTANE; DRUG DERIVATIVE; ETHANE; FLUORINE; WATER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; PH; SYNTHESIS;

BORANES; CATALYSIS; DDT; ETHANE; FLUORINE; HYDROGEN-ION CONCENTRATION; MOLECULAR STRUCTURE; WATER;

EID: 79961065575     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201669a     Document Type: Article

References (45)

1. McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555
2. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320
3. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359
4. Isanbor, C.; O'Hagan, D. J. Fluorine Chem. 2006, 127, 303
5. Wu, Y. C.; Chen, Y. J.; Li, H. J.; Zou, X. M.; Hu, F. Z.; Yang, H. Z. J. Fluorine Chem. 2006, 127, 409
6. Jun, J. Y.; Griffith, J. W.; Bruggeman, R.; Washington, S.; Demers, L. M.; Verderame, M. F.; Manni, A. Breast Cancer Res. Treat. 2007, 105, 29
7. Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757
8. Begue, J. P.; Bonnet-Delpon, D.; Crousse, B.; Legros, J. Chem. Soc. Rev. 2005, 34, 562
9. Funabiki, K.; Matsunaga, K.; Nojiri, M.; Hashimoto, W.; Yamamoto, H.; Shibata, K.; Matsui, M. J. Org. Chem. 2003, 68, 2853
10. Funabiki, K.; Nagaya, H.; Ishihara, M.; Matsui, M. Tetrahedron 2006, 62, 5049
11. Yuefa, G.; Katsuya, K. Curr. Org. Chem. 2004, 8, 1659
12. Billard, T.; Gille, S.; Ferry, A.; Barthelemy, C.; Christophe, C.; Langlois, B. R. J. Fluorine Chem. 2005, 126, 189
13. Yanai, H.; Mimura, H.; Kawada, K.; Taguchi, T. Tetrahedron 2007, 63, 2153
14. Gosselin, F.; Roy, A.; O'Shea, P. D.; Chen, C.-y.; Volante, R. P. Org. Lett. 2004, 6, 641
15. Kaneko, S.; Yamazaki, T.; Kitazume, T. J. Org. Chem. 1993, 58, 2302
16. Ishii, A.; Soloshonok, V. A.; Mikami, K. J. Org. Chem. 2000, 65, 1597
17. Prakash, G. K. S.; Yan, P.; Török, B.; Olah, G. A. Synlett 2003, 527
18. Abid, M.; Török, B. Adv. Synth. Catal. 2005, 347, 1797
19. Kray, W. D.; Rosser, R. W. J. Org. Chem. 1977, 42, 1186 and references therein.
20. O'Connor, M.; Boblak, K. N.; Spitzer, A. D.; Gucciardo, P. A.; Baumann, A. M.; Peter, J. W.; Chen, C. Y.; Peter, R.; Mitton, A. A.; Klumpp, D. A. Tetrahedron Lett. 2010, 51, 4984
21. Klumpp, D. A.; Garza, M.; Sanchez, G. V.; Lau, S.; Leon, S. J. Org. Chem. 2000, 65, 8997
22. Monguchi, Y.; Kume, A.; Sajiki, H. Tetrahedron 2006, 62, 8384
23. Uneyama, K.; Momota, M.; Hayashida, K.; Toshiyuki, I. J. Org. Chem. 1990, 55, 5364 and references therein.
24. Ciongrad, B. M.; Iancu, V. S.; Mate, S.; Stark, V. F.; Buzasiu, A.; Condoros, F.; Juhasz, E. Rom. (1984), RO 82-109278.
25. Kaluszyner, A.; Reuter, S.; Bergmann, E. D. J. Am. Chem. Soc. 1955, 77, 4164
26. DePuy, C. H.; Schultz, A. L. J. Org. Chem. 1974, 39, 878
27. Jarczewski, A.; Shroeder, G.; Galezowski, W. Can. J. Chem. 1985, 63, 576
28. Nutaitis, C. F.; Gribble, G. W. Synthesis 1985, 756
29. Olah, G. A.; Wang, Q.; Trivedi, N; Prakash, G. K. S. Synthesis 1992, 465
30. Olah, G. A.; Wang, Q.; Li, X. Y.; Bucsi, I. Synthesis 1992, 1085
31. Olah, G. A.; Wang, Q.; Li, X. Y.; Prakash, G. K. S. Synthesis 1993, 207
32. Prakash, G. K. S.; Mathew, T.; Hoole, D.; Esteves, P. M.; Wang, Q.; Rasul, G.; Olah, G. A. J. Am. Chem. Soc. 2004, 126, 15770
33. Prakash, G. K. S.; Panja, C.; Mathew, T.; Olah, G. A. Catal. Lett. 2007, 114, 24
34. Prakash, G. K. S.; Paknia, F.; Chacko, S.; Mathew, T.; Olah, G. A. Heterocycles 2008, 76, 783
35. Prakash, G. K. S.; Panja, C.; Shakhmin, A.; Shah, E.; Mathew, T.; Olah, G. A. J. Org. Chem. 2009, 74, 8659
36. Abernathy, C. O.; Hodgson, E.; Guthrie, F. E. Biochem. Pharmacol. 1971, 20, 2385
37. Cohen, S.; Tahori, A. S. J. Agric. Food Chem. 1957, 5, 519
38. Bornstein, J.; Blum, M. S.; Pratt, J. J., Jr. J. Org. Chem. 1957, 22, 1210
39. Guy, A.; Lobgeois, A.; Lemair, M. J. Fluorine Chem. 1986, 32, 361
40. Olah, G. A. Friedel-Crafts and Related Reactions; Wiley-Interscience: New York, 1963.
41. Olah, G. A.; Rasul, G.; York, C.; Prakash, G. K. S. J. Am. Chem. Soc. 1995, 117, 11211
42. Klumpp, D. A.; Garza, M.; Jones, A.; Mendoza, S. J. Org. Chem. 1999, 64, 6702
43. Klumpp, D. A.; Kindelin, P. J.; Li, A. Tetrahedron Lett. 2005, 46, 2931
44. Klumpp, D. A.; Lau, S. J. Org. Chem. 1999, 64, 7309
45. Olah, G. A.; Klumpp, D. A. Superelectrophiles and their Chemistry; Wiley-Interscience: Hoboken, NJ, 2008.