Palladium-catalyzed Suzuki couplings of 2,3-dibromonorbornadiene: Synthesis of symmetrical and unsymmetrical aryl-substituted norbornadienes

European Journal of Organic Chemistry

Volumn , Issue 6, 2005, Pages 1044-1051

  Yoo, Woo Jin ^a   Tsui, Gavin C ^a   Tam, William ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

Boronic acids; Catalysis; Norbornadienes; Palladium; Suzuki couplings

Indexed keywords

2,3 DIBROMONORBORNADIENE; BORONIC ACID DERIVATIVE; CESIUM; FLUORINE DERIVATIVE; NORBORNADIENE DERIVATIVE; PALLADIUM; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; DIELS ALDER REACTION; REACTION ANALYSIS; SONOGASHIRA REACTION; STEREOSPECIFICITY; SUZUKI REACTION;

EID: 15944376577     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400713     Document Type: Article

References (38)

1. E. J. Corey, M. Shibasaki, K. C. Nicolaou, C. L. Malmsten, B. Samuelesson, Tetrahedron Lett. 1976, 17, 737-740.
2. M. Lee, I. Ikeda, T. Kawabe, S. Mori, K. Kanematsu, J. Org. Chem. 1996, 61, 3406-3416.
3. a) K. Sato, O. Miyamoto, S. Inoue, K. Honda, Chem. Lett. 1981, 1183-1184;
4. b) H. Monti, C. Corriol, M. Bertrand, Tetrahedron Lett. 1982, 23, 5539-5540.
5. For reviews, see: a) V. A. Bren, A. D. Dubonosov, V. I. Minkin, V. A. Chernoivanov, Russ. Chem. Rev. 1991, 60, 913-948;
6. b) A. D. Dubonosov, V. A. Bren, V. A. Chernoivanov, Russ. Chem. Rev. 2002, 71, 917-927.
7. For representative examples, see: a) W. G. Dauben, R. L. Cargill, Tetrahedron 1961, 15, 197-201;
8. b) G. S. Hammond, N. J. Turro, A. Fisher, J. Am. Chem. Soc. 1961, 83, 4674-4675;
9. c) N. J. Turro, W. R. Cherry, M. F. Manfred, M. J. Mairbach, J. Am. Chem. Soc. 1977, 99, 7390-7392;
10. d) H. Ikezawa, C. Kutal, K. Yasufuku, H. Yamazaki, J. Am. Chem. Soc. 1986, 108, 1589-1594;
11. e) H. Tomioka, Y. Hamano, Y. Izawa, Bull. Chem. Soc. Jpn. 1987, 60, 821-823;
12. f) A. D. Dubonosov, V. A. Chernoivanov, L. L. Popova, V. A. Rren, V. I. Minkin, Russ. J. Org. Chem. 1994, 30, 160-161;
13. g) R. Herges, W. Reif, Chem. Ber. 1994, 127, 1143-1145;
14. h) V. A. Chernoivanov, A. D. Dubonosov, A. A. Bren, V. I. Minkin, A. N. Suslov, G. S. Borodkin, Mol. Cryst. Liq. Cryst. 1997, 297, 239-245;
15. i) F. Starck, P. G. Jones, R. Herges, Eur. J. Org. Chem. 1998, 2533-2539;
16. j) R. Herges, F. Starck, T. Winkler, M. Schmittel, Chem. Eur. J. 1999, 5, 2965-2969;
17. k) T. Nagai, M. Shimada, Y. Ono, T. Nishikubo, Macromolecules 2003, 36, 1786-1792.
18. a) K. Hirao, A. Ando, T. Hamada, O. Yonemitsu, J. Chem. Soc. Chem., Commun. 1984, 300-302;
19. b) E. E. Bonfantini, D. L. Officer, J. Chem. Soc., Chem. Commun. 1994, 1445-1446;
20. c) S. M. Aldoshin, V. A. Bren, A. D. Dubonosov, O. A. Kozina, V. I. Minkin, V. A. Chernoivanov, I. I. Chuev, Russ. Chem. Bull. 1995, 44, 487-491;
21. d) M. Maafi, C. Lion, J. J. Aaron, New. J. Chem. 1996, 20, 559-570;
22. e) F. Franceschi, M. Guardigli, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 1997, 36, 4099-4107;
23. f) A. Ikeda, A. Tsubata, A. Kameyama, T. Nishikubo, J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 917-926.
24. a) T. Nishikubo, T. Shimokawa, A. Sahara, Macromolecules 1989, 22, 8-14;
25. b) K. Kinoshita, K. Horie, S. Morino, T. Nishikudo, Appl. Phys. Lett. 1997, 70, 2940-2942;
26. c) S. Takahashi, K. Samata, H. Mura, S. Machida, K. Horie, Appl. Phys. Lett. 2001, 78, 13-15.
27. Y. Kato, H. Muta, S. Takahashi, K. Horie, T. Nagai, Polym. J. 2001, 33, 868-873.
28. T. Winkler, I. Dix, P. G. Jones, R. Herges, Angew. Chem. Int. Ed. 2003, 42, 3541-4544.
29. a) E. Ciganek, Org. React. 1984, 32, 1-374;
30. b) The Diels-Alder Reaction (Eds.: F. Fringuelli, A. Taticchi), John Wiley & Sons, West Sussex, 2002.
31. G. K. Tranmer, C. Yip, S. Handerson, R. W. Jordan, W. Tam, Can. J. Chem. 2000, 78, 527-535.
32. G. K. Tranmer, W. Tam, Synthesis 2002, 1675-1682.
33. For reviews, see: a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483;
34. b) A. Suzuki, in Metal-Catalyzed Cross Coupling Reactions (Eds.: F. Diederich, P. J. Stang), chapter 2, Wiley-VCH, Weinheim, Germany, 1998;
35. c) A. Suzuki, J. Organomet. Chem. 1999, 576, 147;
36. d) N. Miyaura, Top. Curr. Chem. 2002, 219, 11-59;
37. e) M. Miura, Angew. Chem. Int. Ed. 2004, 43, 2201-2203.
38. Norbornadienes 10a-10d were synthesized by mono lithium-halide exchange of 2,3-dibromonorbornadiene 2 followed by trapping with the corresponding electrophiles (R = Me: MeI, R = TBS: TBSCl, R = COOEt: ethyl chloroformate, R = Cl: TsCl). See ref[11] for details.