Synthesis of 8,9-disubstituted fluoranthenes by domino two-fold Heck/electrocyclization/dehydrogenation of 1,2-dibromoacenaphthylene

Tetrahedron Letters

Volumn 52, Issue 16, 2011, Pages 1888-1890

  Ullah, Ihsan ^a   Nawaz, Muhammad ^a   Villinger, Alexander ^a   Langer, Peter ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Catalysis; Domino reaction; Fluoranthenes; Heck reaction; Palladium

Indexed keywords

8,9 DISUBSTITUTED FLUORANTHENE; FLUORANTHENE; UNCLASSIFIED DRUG;

ARTICLE; DEHYDROGENATION; DRUG STRUCTURE; DRUG SYNTHESIS; HECK REACTION;

EID: 79952736437     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.02.032     Document Type: Article

References (50)

1. (a) Manoli, E.; Kouras, A.; Samara, C. Chemsphere 2004, 56, 867;
2. (b) Lodovici, M.; Venturini, M.; Marini, E.; Grechi, D.; Dolara, P. Chemosphere 2003, 50, 3377.
3. (a) Boden, N.; Bushby, R. J.; Cammidge, A. N. J. Am. Chem. Soc. 1995, 117, 924;
4. (b) Bushby, R. J.; Lu, Z. Synthesis 2001, 763;
5. (c) Rathore, R.; Burns, C. L. J. Org. Chem. 2003, 68, 4071. and references cited therein;
6. (d) Watson, M. D.; Fechtenkötter, A.; Müllen, K. Chem. Rev. 2001, 101, 1267. and references cited therein;
7. (e) Law, K. Y. Chem. Rev. 1993, 93, 449;
8. (f) Enkelmann, V. Synth. Met. 1991, 42, 2547.
9. (a) Plummer, B. F.; Singleton, S. F. J. Phys. Chem. 1990, 94, 7363;
10. (b) Plummer, B. F.; Hall, R. A. J. Chem. Soc., Chem. Commun. 1970, 44-46;
11. (c) Plummer, B. F.; Reese, W. G.; Watson, W. H.; Kashyep, R. P. Struct. Chem. 1993, 4, 53;
12. (d) Cho, B. P.; Harvey, R. G. J. Org. Chem. 1987, 52, 5668;
13. (e) Plummer, B. F.; Steffen, L. K.; Herndon, W. C. Struct. Chem. 1993, 4, 1993.
14. Gutman, I.; Duerdevic, J.; Radenkovic, S.; Burmudzija, A. Indian J.Chem. 2009, 48, 194.
15. (a) Shenbor, M. I.; Tikhonov, V. I.; Kunavin, N. I. J. Appl. Spectrosc. 1975, 23, 1470;
16. (b) Berlman, I. B.; Goldschmidt, C. R.; Stein, G.; Tomkiewicz, Y.; Weinreb, A. Chem. Phys. Lett. 1969, 4, 338-340;
17. (c) Bark, K.-M.; Forcé, R. K. Spectrochim. Acta, Part A 1993, 49, 1605;
18. (d) Heinrich, G.; Güsten, H. Fresenius J. Anal. Chem. 1976, 278;
19. (e) Branchi, B.; Balzani, V.; Ceroni, P.; Kuchenbrandt, M. C.; Klärner, F. G.; Bläser, D.; Boese, R. J. Org. Chem. 2008, 73, 5839;
20. (f) Yan, Q.; Zhou, Y.; Ni, B.-B.; Ma, Y.; Wang, J.; Pei, J.; Cao, Y. J. Org. Chem. 2008, 73, 5328;
21. (g) Goel, A.; Kumar, V.; Chaurasia, S.; Rawat, M.; Prasad, R.; Anand, R. S. J. Org. Chem. 2010, 75, 3656;
22. (h) Marciniak, B. J. Cryst. Growth 2002, 236, 333;
23. (i) Chiechi, R. C.; Tseng, R. J.; Marchioni, F.; Yang, Y.; Wudl, F. Adv. Mater. 2006, 18, 325;
24. (j) Ma, X.; Wu, W.; Zhang, Q.; Guo, F.; Meng, F.; Hua, J. Dyes Pigm. 2009, 82, 353.
25. Stocker, K. J.; Howard, W. R.; Statham, J.; Proudlock, R. J. Mutagenesis 1996, 11, 493.
26. (a) Vasilikov, A. Y. Russ. J. Electrochem. 2003, 39, 1342;
27. (b) Pothuluri, J. V.; Heflich, R. H.; Fu, P. P.; Cerniglia, C. E. Appl. Environ. Microbiol. 1992, 58, 937.
28. (a) Cho, B. P.; Harvey, R. G. Tetrahedron Lett. 1987, 28, 861;
29. (b) Laali, K. K.; Okazaki, T.; Galembeck, S. E. J. Chem. Soc., Perkin Trans. 2 2002, 621.
30. Albrecht, W. L.; Fleming, R. W.; Horgan, S. W.; Deck, B. A.; Hoffman, J. W.; Mayer, G. D. J. Med. Chem. 1974, 17, 1150.
31. (a) Gonzalez, J. J.; Francesch, A.; Cardenas, D. J.; Echavarren, A. M. J. Org. Chem. 1998, 63, 2854-2857;
32. (b) Preda, D. V.; Scott, L. T. Org. Lett. 2000, 2, 1489-1492.
33. (a) Cho, B. P. Tetrahedron Lett. 1995, 36, 2403;
34. (b) Panda, K.; Venkatesh, C.; Hiriyakkanavar, J. Eur. J. Org. Chem. 2005, 2045-2055;
35. (c) Wu, Y.-T.; Hayama, T.; Baldridge, K. K.; Linden, A.; Siegel, J. S. J. Am. Chem. Soc. 2006, 128, 6870;
36. (d) Dewar, M. J. S.; Michl, J. Tetrahedron 1970, 26, 375;
37. (e) Meth-Cohn, O.; van Vuuren, G. Tetrahedron Lett. 1986, 27, 1105;
38. (f) Matsushita, Y.-i.; Sakamoto, K.; Murakami, T.; Matsui, T. Synth. Commun. 1994, 24, 3307;
39. (g) Wehmeier, M.; Wagner, M.; Müllen, K. Chem. Eur. J. 2001, 7, 2197;
40. (h) Debad, J. D.; Morris, J. C.; Lynch, V.; Magnus, P.; Bard, A. J. J. Am. Chem. Soc. 1996, 118, 2374.
41. Voigt, K.; von Zezschwitz, P.; Rosauer, K.; Lansky, A.; Adams, A.; Reiser, O.; de Meijere, A. Eur. J. Org. Chem. 1998, 1521.
42. (a) Hussain, M.; Dang, T. T.; Langer, P. Synlett 2009, 1822;
43. (b) Toguem, S.-M. T.; Hussain, M.; Malik, I.; Villinger, A.; Langer, P. Tetrahedron Lett. 2009, 50, 4962;
44. (c) Hussain, M.; Hung, N. T.; Langer, P. Tetrahedron Lett. 2009, 50, 3929;
45. (d) Toguem, S.-M. T.; Langer, P. Synlett 2010, 1779.
46. Kurata, H.; Takehara, Y.; Kim, S.; Sakai, K.; Matsumoto, K.; Kawase, T.; Oda, M. Synlett 2007, 2053.
47. A single example of a Kumada coupling with an alkenylmagnesium species and subsequent electrocyclization has been reported: Rathore, R.; Lindeman, S. V.; Kumar, A. S.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 6012.
48. Trost, B. M.; Brittelli, D. R. J. Org. Chem. 1967, 32, 2620.
49. +: 402.18256. Found: 402.183102.
50. CCDC 811880 contain all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ; Fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk.