Application of a new combination of palladium and CaCo3 for an aerobic heck reaction using arenediazonium-salts

Tetrahedron Letters

Volumn 40, Issue 26, 1999, Pages 4815-4818

  Brunner, Heiko ^a   De Courcy, Nathalie Le Cousturier ^a   Genêt, Jean Pierre ^a  

^a PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; CALCIUM CARBONATE; DIAZONIUM COMPOUND; FUNCTIONAL GROUP; NITRO DERIVATIVE; PALLADIUM;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; REACTION ANALYSIS;

EID: 0033603569     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00921-1     Document Type: Article

References (37)

1. a) Heck, R.F. Palladium Reagents in Organic Synthesis, Academic Press, London, 1985.
2. b) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, Chichester, 1995.
3. c) De Meijere, A.; Meyer, F.E. Angew. Chem. 1994, 106, 2473-2506; Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411.
4. c) De Meijere, A.; Meyer, F.E. Angew. Chem. 1994, 106, 2473-2506; Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411.
5. d.) Cabri, W., Candiani, I. Acc. Chem. Res. 1995, 28, 2-7.
6. e) Jeffery, T. Adv. Met.-org. Chem. 1996, 5, 153-260.
7. f) Crisp, G.T., Chem. Soc. Rev. 1998, 27, 427-436.
8. g) Bräse, S., de Meijere, A. in Metal-catalvzed Cross-coupling Reactions, Diederich, F., Stang, P.J. Ed., Wiley-VCH, Weinheim, 1998
9. Cornils, B.; Herrmann, W.A. Applied Homogeneous Catalysis with Organometallic Compounds, VCH, Weinheim, 1996.
10. Stephan, M.S.; Teunissen, A.J.J.M.; Verzijl, G.K.M.; De Vries, J.G. Angew. Chem. 1998, 110, 688- 690; Angew. Chem. Int. Ed. Engl. 1998, 37, 662-664.
11. Stephan, M.S.; Teunissen, A.J.J.M.; Verzijl, G.K.M.; de Vries, J.G. Angew. Chem. 1998, 110, 688- 690; Angew. Chem. Int. Ed. Engl. 1998, 37, 662-664.
12. a) Blaser, H.-U.; Spencer, A.; J. Organomet. Chem. 1982, 233, 267-274.
13. b) Spencer, A.; J. Organomet. Chem. 1982, 240, 209-216.
14. c) Spencer, A.; J. Organomet. Chem. 1984, 265, 323-331.
15. Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-catalyzed Organic Reactions, Academic Press, San Diego 1997 and therein cited literature.
16. a) Yong, W.; Yi, P.; Zhuangyu, Z.; Hongwen, H., Synthesis 1991,967-969.
17. b) Ikenaga, K.; Matsumoto, S.; Kikukawa, K.; Matsuda, T., Chem.lett. 1988, 873-876.
18. c) Ikenaga, K.; Kikukawa, K., Matsuda, T., J. Chem. Soc., Perkin Trans L 1986, 1959-1964.
19. d) Kikukawa, K., Nagira, K., Wada, F., Matsuda, T., Tetrahedron 1981, 37, 31-36.
20. e) Sengupta, S., Sadhukan, K., Bhattacharyya, S.,Tetrahedron 1997, 53, 2213-2218.
21. f) Sengupta, S.; Bhattacharyya, S., J. Chem. Soc., Perkin Trans L 1993, 1943-1944;
22. g) Sengupta, S., Sadhukhan, S.K., Tetrahedron Lett. 1998; 39, 715-718.
23. h) Sengupta, S., Sadhukan, S.K., Bhattacharyya, S., Guha, J., J. Chem. Soc., Perkin Trans L 1998, 407-410 and therein cited literature.
24. a) Darses, S., Genêt, J.-P., Brayer, J.-L., Demoute, J.-P., Tetrahedron Lett. 1997, 38, 4393-4396.
25. b) Darses, S., Jeffery, T., Genêt, J.-P., Brayer, J.-L., Demoute, J.-P., Tetrahedron Lett. 1996, 37, 3857- 3860.
26. c) Darses, S., Jeffery, T., Brayer, J.-L., Demoute, J.-P., Genêt, J.P. Bull. Soc. Chim. Fr. 1996, 133, 1095-1102.
27. d) Darses, S., Michaud, G., Genêt, J.-P., Tetrahedron Lett. 1998, 39, 5045-5048.
28. e) Sengupta, S.; Bhattacharyya, S, J. Org. Chem. 1997, 62, 3405-3406.
29. Kikukawa et al. have only used acetonitrile and dichloromethane as solvents and have gradualy given the arenediazonium-salts to the reaction-mixture (ref. 6c).
30. Beller, M., Kühlein, K., Synlett 1995, 441-442.
31. a) Kirk-Othmer, Encyclopedia of Chemical Technology, 1979, Wiley Interscience, New York, Vol.7, p.153, C.A. 108; 37401f.
32. b) Garbe, D. in Ullmann Encyclopedia, 1992, Vol. A7, 99.
33. a) Zimmer, H.; Pampalone, T., J. Heterocycl. Chem. 1965, 2, 95-96.
34. b) Katsumi, I.; Kondo, H.; Yamashita, K.; Hidaka, T.; Hosoe, K; Yamashita, T.; Watanabe, K., Chem. Pharm. Bull. 1986, 34, 121-129 and therin cited literature.
35. c) Lee, E.; Hur, C.U.; Jeong, Y.C.; Rhee, Y.H.; Chang, M.H., J. Chem. Soc. Chem. Commun. 1991,18, 1314-1315.
36. To our knowledge only one application for the synthesis of podophyllotoxins has been described. For a reference see Ishibashi, H.; Ito, K.; Hirano, T.; Tabuchi, M.; Ikeda, M., Tetrahedron 1993, 49, 4173- 4182 and therein cited literature.
37. 3 are suspended in 5 mL solvent. Subsequently 1 mmol of the acrylic acid ester is added and the mixture is warmed. After the reaction is completed the solvent is evaporated and the residue is purified by flash chromatography on silica.