Synthesis of aryl-substituted naphthalenes by chemoselective Suzuki-Miyaura reactions of bromo-trifluoromethanesulfonyloxy-naphthalenes. Influence of steric and electronic parameters

Tetrahedron

Volumn 68, Issue 31, 2012, Pages 6305-6313

  Hassan, Zahid ^a   Hussain, Munawar ^a   Villinger, Alexander ^a   Langer, Peter ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Catalysis; Chemoselectivity; Naphthalene; Naphthaquinones; Palladium; Suzuki Miyaura reaction; Tetralone

Indexed keywords

1 (4 TERT BUTYLPHENYL) 2 (2 METHOXYPHENYL)NAPHTHALENE; 1,2 BIS(2 METHOXYPHENYL)NAPHTHALENE; 1,2 BIS(4 CHLOROPHENYL)NAPHTHALENE; 1,2 BIS(4 METHYLPHENYL)NAPHTHALENE; 2 (4 CHLOROPHENYL) 1 (3,5 DIMETHYLPHENYL)NAPHTHALENE; 2 (4 FLUOROPHENYL) 1 (3 TOLYL)NAPHTHALENE; 2 (4 METHYLPHENYL) 1 (2,5 DIMETHOXYPHENYL)NAPHTHALENE; 2 (PHENYL) 1 (2 METHOXYPHENYL)NAPHTHALENE; ACETIC ACID DERIVATIVE; BROMIDE; CARBON; NAPHTHALENE DERIVATIVE; TETRALIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; HETERONUCLEAR MULTIPLE BOND CORRELATION; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; STEREOSPECIFICITY; SUZUKI MIYAURA REACTION; SUZUKI REACTION; X RAY CRYSTALLOGRAPHY;

EID: 84862662980     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.05.026     Document Type: Article

References (38)

1. de Koning, C. B.; Michael, J. P.; van Ottelo, W. A. L. Tetrahedron Lett. 1999, 40, 3037.
2. Manfredi, K. P.; Blunt, J. W.; Cardellina, J. H., II; Macmahon, J. B.; Pannell, L. K.; Cragg, G. M.; Boyd, M. R. J. Med. Chem. 1991, 34, 3402.
3. (a) Bringmann, G.; Gotz, R.; Keller, P. A.; Walter, R.; Boyd, M. R.; Lang, F.; Garcia, A.; Walsh, J. J.; Tellitu, I.; Bhaskar, K. V.; Kelly, T. R. J. Org. Chem. 1998, 63, 1090;
4. (b) Bringmann, G.; Gotz, R.; Harmsen, S.; Holenz, J.;Walter, R. Liebigs Ann. Chem. 1996, 2045;
5. (c) Hobbs, P. D.; Upender, V.; Dawson, M. I. Synlett 1997, 965;
6. (d) Hobbs, P. D.; Upender, V.; Liu, J.; Pollart, D. J.; Thomas, D. W.; Dawson, M. I. Chem. Commun. 1996, 923;
7. (e) Bringmann, G.; Harmsen, S.; Holenz, J.; Geuder, T.; Gotz, R.; Keller, P. A.; Walter, R.; Ha]lock, Y. F.; Cardellina, J. H., II; Boyd, M. R. Tetrahedron 1994, 50, 9643;
8. (f) Kelly, T. R.; Garcia, A.; Lang, F.; Walsh, J. J.; Bhaskar, K. V.; Boyd, M. R.; Gotz, R.; Keller, P. A.; Walter, R.; Bringmann, G. Tetrahedron Lett. 1994, 35, 7621;
9. (g) Hoye, T. R.; Chen, M.; Mi, L.; Priest, O. P. Tetrahedron Lett. 1994, 47, 8747.
10. Aggarwal, B. B.; Bhardwaj, A.; Aggarwal, R. S.; Seeram, N. P.; Shishodia, S.; Takada, Y. Anticancer Res. 2004, 24, 2783.
11. Jang, M.; Cai, L.; Udeani, G. O.; Slowing, K. V.; Thomas, C. F.; Beecher, C. W.; Fong, H. H.; Farnsworth, N. R.; Kinghorn, A. D.; Mehta, R. G.; Moon, R. C.; Pezzuto, J. M. Science 1997, 275, 218.
12. (a) Signorelli, P.; Ghidoni, R. J. Nutr. Biochem. 2005, 16, 449;
13. (b) Minutolo, F.; Sala, G.; Bagnacani, A.; Bertini, S.; Carboni, I.; Placanica, G.; Prota, G.; Rapposelli, S.; Sacchi, N.; Macchia, M.; Ghadoni, R. J. Med. Chem. 2005, 48, 6783;
14. (c) Viswanathan, G. S.;Wang, M.; Li, C. J. Angew. Chem., Int. Ed. 2002, 41, 2138;
15. (d) Kozik1, B.; Burgie, Z. J.; Sepiot, J. J.; Wilamowski, J.; Kuczynski, M.; Góra1, M. Environ. Biotechnol. 2006, 20.
16. (a) Crawford, G. J. Am. Chem. Soc. 1939, 61, 608;
17. (b) Bergmann, F.; Echinazi, E.; Schapiro, D. J. Am. Chem. Soc. 1942, 64, 557.
18. For reviews of cross-coupling reactions of polyhalogenated heterocycles, see: (a) Schröter, S.; Stock, C.; Bach, T. Tetrahedron 2005, 61, 2245;
19. (b) Schnürch, M.; Flasik, R.; Khan, A. F.; Spina, M.; Mihovilovic, M. D.; Stanetty, P. Eur. J. Org. Chem. 2006, 3283.
20. For palladium-catalyzed reactions from our group, see for example: (a) Dang, T. T.; Dang, T. T.; Ahmad, R.; Reinke, H.; Langer, P. Tetrahedron Lett. 2008, 49, 1698;
21. (b) Dang, T. T.; Villinger, A.; Langer, P. Adv. Synth. Catal. 2008, 350, 2109;
22. (c) Hussain, M.; Nguyen, T. H.; Langer, P. Tetrahedron Lett. 2009, 50, 3929;
23. (d) Dang, T. T.; Dang, T. T.; Rasool, N.; Villinger, A.; Langer, P. Adv. Synth. Catal. 2009, 351, 1595.
24. (a) Kamikawa, T.; Hayashi, T. Tetrahedron Lett. 1997, 38, 7087;
25. (b) Littke, A. F.; Dai, C. Y.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020;
26. (c) Roy, A. H.; Hartwig, J. F. Organometallics 2004, 23, 194;
27. (d) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704;
28. (e) Espino, G.; Kurbangalieva, A.; Brown, J. M. Chem. Commun. 2007, 1742 and references cited therein.
29. Hassan, Z.; Hussain, M.; Langer, P. Synlett 2011, 1827.
30. Bekaert, A.; Provot, O.; Rasolojaona, O.; Alami, M.; Brion, J.-D. Tetrahedron Lett. 2005, 46, 4187.
31. (a) Bolton, R. In Bromine Compounds: Chemistry and Applications; Price, D., Iddon, B., Wakefield, B. J., Eds.; Elsevier: Amsterdam, 1988; p 151;
32. (b) de Kimpe, N.; Verhé, R. In The Chemistry of α-Haloketones, α-Haloaldehydes and α-Haloimines; Patai, S., Rappoport, Z., Eds.; Wiley: 1988.
33. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457;
34. (b) Miyaura, N. Top. Curr. Chem. 2002, 219, 11;
35. (c) Suzuki, A.; Yamamoto, Y. Chem. Lett. 2011, 40, 894.
36. CCDC 871741e871745 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.
37. Pena, P.; Perez, D.; Guitián, E.; Castedo, L. J. Org. Chem. 2000, 65, 6944.
38. Abid, O.-u.-R.; Ibad, M. F.; Nawaz, M.; Sher, M.; Rama, N. H.; Villinger, A.; Langer, P. Tetrahedron Lett. 2010, 51, 1541.