Highly selective palladium-catalyzed Heck reactions of aryl bromides with cycloalkenes

Organic Letters

Volumn 1, Issue 5, 1999, Pages 709-711

  Hartung, Christian G ^a   Köhler, Klaus ^a   Beller, Matthias ^b  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001637540     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9901063     Document Type: Article

References (23)

1. (a) Beller, M.; Riermeier, T. H.; Stark, G. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; VCH: Weinheim, Germany, 1998; p 208.
2. (b) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, U.K., 1995.
3. (c) de Meijere, A.; Meyer, F. Angew. Chem. 1994, 106, 2473; Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
4. (c) de Meijere, A.; Meyer, F. Angew. Chem. 1994, 106, 2473; Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
5. (d) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M., Flemming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 4, p 833.
6. (a) Larock, R. C. Pure Appl. Chem. 1990, 62, 653.
7. (b) Harrington, O. J.; DiFiore, K. A. Tetrahedron Lett. 1987, 28, 495.
8. (c) Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529.
9. (d) Lee, T. D.; Daves, G. D., Jr. J. Org. Chem. 1983, 48, 399.
10. (e) Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21.
11. (f) Tamaru, Y.; Yamada, Y.; Yoshida, Z. Tetrahedron 1979, 35, 329.
12. (g) Heck, R. F. Acc. Chem. Res. 1979, 12, 146.
13. (h) Cortese, N. A.; Ziegler, C. B., Jr.; Hrnjez, B. J.; Heck, R. F. J. Org. Chem. 1978, 43, 2953.
14. Larock, R. C.; Baker, B. E. U.S. Patent 4 879426, 1988.
15. (a) Loiseleur, O.; Hayashi, M.; Schmees, N.; Pfaltz, A. Synthesis 1997, 1338.
16. (b) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603.
17. (c) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047.
18. (d) Larock, R. C.; Baker, B. E. Tetrahedron Lett. 1988, 29, 905.
19. (e) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31.
20. Selectivities were determined by GC on the basis of area percentage.
21. Conversions and yields were determined by GC with internal standard (diethylene glycol di-n-butyl ether).
22. Beller, M.; Riermeier, T. H. Tetrahedron Lett. 1996, 37, 6535.
23. 13C NMR and mass spectroscopy and by comparison with authentic samples by GC.