Condensations of aryl trifluoromethyl ketones with arenes in acidic media

Tetrahedron Letters

Volumn 51, Issue 38, 2010, Pages 4984-4987

  O'Connor, Matthew J ^a   Boblak, Kenneth N ^a   Spitzer, Ashley D ^a   Gucciardo, Peter A ^a   Baumann, Andrew M ^a   Peter, Joshua W ^a   Chen, Connie Y ^a   Peter, Ronald ^a   Mitton, Adam A ^a   Klumpp, Douglas A ^a  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE DERIVATIVE; ACID; CARBONYL DERIVATIVE; ELECTROPHILE; KETONE; POLYCYCLIC AROMATIC HYDROCARBON; QUINOLINE DERIVATIVE; TOLUENE;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; HYDROXYLATION; LOW TEMPERATURE; MASS FRAGMENTOGRAPHY; PROTON TRANSPORT; SYNTHESIS;

EID: 78549272978     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.067     Document Type: Article

References (19)

1. Hofmann, J. E.; Schriesheim, A.. In Friedel-Crafts and Related Reaction; Olah, G. A., Ed.; Wiley: New York, NY, 1964; Vol. 2, pp 597-640;
2. March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, NY, 1992. pp 548-549.
3. Kray, W. D.; Rosser, R. W. J. Org. Chem. 1977, 42, 1186;
4. Khodakovskly, P. V.; Mykhailiuk, P. K.; Volochnyuk, D. M. Synthesis 2010, 967;
5. Prakash, G. K. S.; Panja, C.; Shakhmin, A.; Shah, E.; Mathew, T.; Olah, G. A. J. Org. Chem. 2009, 74, 8659.
6. Prakash, G. K. S.; Paknia, F.; Chacko, S.; Mathew, T.; Olah, G. A. Heterocycles 2008, 76, 783;
7. O'Connor, M.; Boblak, K.; Topinka, M.; Briski, J.; Kindelin, P.; Zheng, C.; Klumpp, D. K. J. Am. Chem. Soc. 2010, 113, 3266
8. Sheets, M. A.; Li, A.; Bower, E. A.; Weigel, A. R.; Abbott, M. P.; Gallo, R. M.;Mitton, A. A.; Klumpp, D. A. J. Org. Chem. 2009, 73, 2502.
9. Ohwada, T.; Yamagata, N.; Shudo, K. J. Am. Chem. Soc. 1991, 113, 1364.
10. Diaz, A. M.; Zolotukhin, M.; Fromine, S.; Salcedo, S.; Manero, O.; Cedillo, G.; Velasco, V. M.; Guzman, M. T.; Fritsch, D.; Khalizov, A. F. Macromol. Rapid Commun. 2007, 28, 183;
11. Zolotukhin, M.; Fromine, S.; Salcedo, S.; Khalilov, L. Chem. Commun. 2004, 1030.
12. Guzman-Gutierrez, M. T.; Zolotukhin, M. G.; Fritsch, D.; Ruiz-Trevino, F. A.; Cedillo, G.; Fregoso-Israel, E.; Ortiz-Estrada, C.; Chavez, J.; Kudla, C. J. Membr. Sci. 2008, 323, 379.
13. Rusanov, A. L.; Chebotarev, V. P.; Lovkov, S. S. Russ. Chem. Rev. 2008, 77, 547;
14. Fu, Y.; Van Oosterwijck, C.; Vandendriessche, A.; Kowalczuk-Bleja, A.;Zhang, X.; Dworak, A.; Dehaen, W.; Smet, M. Macromolecules 2008, 41, 2388.
15. 4 and isolated by column chromatography or recrystallization. In the case of compound 20, 2 mmol of benzo-18-crown-6 is reacted with 1 mmol of compound 7.
16. Olah, G. A.; Berrier, A.; Prakash, G. K. S. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 1998.
17. Olah, G. A.; Prakash, G. K. S.; Molnar, A.; Sommer, J. Superacid Chemistry, 2nd ed.; Wiley & Sons: New York, 2009.
18. Alternatively, hydride transfer might occur after arylation and formation of the carbocation intermediate. Products 25-27 could not be separated; their identities and relative yields were established by GC-MS, GC-FID, and 1H NMR analysis of the crude product mixture.
19. 3: 40.1, 63.5 (q, JC-F = 24 Hz), 111.8, 124.8, 127.1 (q, JC-F = 284 Hz), 129.2, 130.1, 130.3, 131.8, 132.5, 132.7, 140.7, 150.4. LR MS: 495/493/491 (M+), 426/424/422, 175. HRMS, C22H16NCl43 calcd 490.99888, found 490.99808.