Facile synthesis of 1,7,8-trifluoro-2-naphthol via DMAP catalyzed cycloaromatization

Journal of Fluorine Chemistry

Volumn 157, Issue , 2014, Pages 41-47

  Araki, Keisuke ^a   Katagiri, Tomohiro ^b   Inoue, Munenori ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^b TOKAI UNIVERSITY   (Japan)

Author keywords

1,7,8 Trifluoro 2 naphthol; Deoxyfluorination; Intramolecular cycloaromatization; Liquid crystal compounds; Suzuki Miyaura vinylation

Indexed keywords

EID: 84888235806     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2013.11.005     Document Type: Article

References (36)

1. M. Hird, and K. Toyne Mol. Cyst. Liq. Cryst. 323 1998 1 67
2. P. Kirsch, and M. Bremer Angew. Chem. Int. Ed. 39 2000 4216 4235
3. M. Hird, J.W. Goodby, R.A. Lewis, and K.J. Toyne Mol. Cyst. Liq. Cryst. 401 2003 1 18
4. P. Kirsch Modern Fluoroorganic Chemistry 2004 Wiley-VCH Weinheim
5. M. Hird Chem. Soc. Rev. 36 2007 2070 2095
6. M. Bremer, P. Kirsch, M. Klasen-Memmer, and K. Tarumi Angew. Chem. Int. Ed. 52 2013 8880 8896
7. J. Manero, R.W. Fuss, and B. Hornung Chem. Abstr. 124 1996 260617
8. T. Matsumoto, Y. Nagashima, and T. Kusumoto Chem. Abstr. 143 2005 376544
9. C.-Z. Li, S. Takehara, Y. Nagashima, and T. Kusumoto Chem. Abstr. 144 2006 302158
10. T. Kusumoto, Y. Nagashima, S. Takehara, and T. Matsumoto Chem. Abstr. 140 2004 312432
11. T. Matsumoto, and T. Kusumoto Chem. Abstr. 142 2005 373571
12. K. Yokota, and Y. Ka Chem. Abstr. 147 2007 448536
13. Y. Nagashima, and T. Kusumoto Chem. Abstr. 148 2008 225781
14. A.G. Myers, and Y. Horiguchi Tetrahedron Lett. 38 1997 4363 4366
15. S. Kawata, S. Ashizawa, and M. Hirama J. Am. Chem. Soc. 119 1997 12012 12013
16. T. Saito, M. Morimoto, C. Akiyama, T. Matsumoto, and K. Suzuki J. Am. Chem. Soc. 117 1995 10757 10758
17. T. Saito, T. Suzuki, M. Morimoto, C. Akiyama, T. Ochiai, K. Takeuchi, T. Matsumoto, and K. Suzuki J. Am. Chem. Soc. 120 1998 11633 11644
18. J.H. Rupard, T. de Paulis, A. Janowsky, and H.E. Smith J. Med. Chem. 32 1989 2261 2268
19. S.G. Gilbreath, C.M. Harris, and T.M. Harris J. Am. Chem. Soc. 110 1988 6172 6179
20. N. Sotomayor, E. Domínguez, and E. Lete Tetrahedron Lett. 35 1994 2973 2976
21. D.-H. Wang, K.M. Engle, B.-F. Shi, and J.-Q. Yu Science 327 2010 315 319
22. G.A. Molander, and M.R. Rivero Org. Lett. 4 2002 107 109
23. G.A. Molander, and A.R. Brown J. Org. Chem. 71 2006 9681 9686
24. G.A. Molander, and R. Figueroa Aldrichim. Acta 38 2005 49 56
25. G.A. Molander, and N. Ellis Acc. Chem. Res. 40 2007 275 286
26. S. Darses, and J.-P. Genet Chem. Rev. 108 2008 288 325
27. S.E. Denmark, and C.R. Butler Chem. Commun. 2009 20 33
28. C.G. Bashore, M.G. Vetelino, M.C. Wirtz, P.R. Brooks, H.N. Frost, R.E. McDermott, D.C. Whritenour, J.A. Ragan, J.L. Rutherford, T.W. Makowski, S.J. Brenek, and J.W. Coe Org. Lett. 8 2006 5947 5950
29. W.J. Middleton J. Org. Chem. 40 1975 574 578
30. G.S. Lal, G.P. Pez, R.J. Pesaresi, and F.M. Prozonic Chem. Commun. 1999 215 216
31. G.S. Lal, G.P. Pez, R.J. Pesaresi, F.M. Prozonic, and H. Cheng J. Org. Chem. 64 1999 7048 7054
32. A. Takaoka, H. Iwakiri, and N. Ishikawa Bull. Chem. Soc. Jpn. 52 1979 3377 3380
33. V.A. Petrov, S. Swearingen, W. Hong, and W.C. Petersen J. Fluorine Chem. 109 2001 25 31
34. N.N. Yarovenko, M.A. Raksha, and Zh. Obshch Khim 29 1959 2159 2163
35. F. Beaulieu, L.-P. Beauregard, G. Courchesne, M. Couturier, F. LaFlamme, and A. L'Heureux Org. Lett. 11 2009 5050 5053
36. F. Kerins, and D.F. O'Shea J. Org. Chem. 67 2002 4968 4971