First efficient palladium-catalyzed Heck reactions of aryl bromides with alkyl methacrylate

Tetrahedron Letters

Volumn 37, Issue 36, 1996, Pages 6535-6538

  Beller, Matthias ^a   Riermeier, Thomas H ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BENZENE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030565564     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01442-6     Document Type: Article

References (20)

1. Part 5 of the series Palladium-Catalyzed Reactions in Industry, for part 4 see Beller, M.; Riermeier, T. H.; Haber, S.; Kleiner, H.-J.; Herrmann, W. A. Chem. Ber. 1996 in print.
2. (a) Tsuji, J. Palladium Reagents and Catalysts, John Wiley & Sons, Chichester, 1995.
3. (b) Meijere, A. de; Meyer, F. Angew. Chem. 1994, 106, 2473;
4. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.
5. Heck, R. F.; in Trost, B.; Flemming I. (Eds.) Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991, Vol. 4, p. 833.
6. Heck, R. F. Palladium Reagents in Organic Synthesis, Academic Press, London, 1985.
7. 51 see Spencer, A. J. Organomet, Chem., 1983, 247, 117;
8. for recent improvement under high pressure conditions see: Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087.
9. (a) Patel, B. A.; Ziegler, C. B.; Cortese, N. A.; Plevyak, J. E.; Zebovitz, T. C.; Terpko, M.; Heck, R. F. J. Org. Chem. 1977, 42, 3903.
10. (b) Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083.
11. (c) Kasahara, A.; Izumi, T.: Maemura, M. Bull. Chem. Soc. Jpn. 1977, 50, 1021.
12. Herrmann, W. A.; Broßmer, C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem. 1995, 107, 1989;
13. Angew. Chem. Int. Ed. Engl. 1995, 34, 1844.
14. Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Broßmer, C. Angew. Chem. 1995, 107, 1992;
15. Angew. Chem. Int. Ed. Engl. 1995, 34, 1848.
16. Selectivities have been determined by GC on the basis of area percentage.
17. Conversions have been determined by GC with internal standard (diethyleneglycoldibutyl ether).
18. Determined by a kinetic study of the reaction of 4-bromofluorobenzene and butyl methacrylate with 0.01 mol% 3 and sodium acetate as base (5 h).
19. 4. After removal of the solvent the desired products were isolated as a colourless oil (7.12 g, 60 %) by distillation in vacuo (b.p.: 95-100 °C / 1 mbar).
20. The reaction has been upscaled to 100 g scale for the synthesis of substituted indanones. M. Beller, T. H. Riermeier, S. Klein, K. Kühlein, unpublished results.