Sonogashira cross-coupling reactions catalysed by heterogeneous copper-free Pd-zeolites

Tetrahedron Letters

Volumn 45, Issue 7, 2004, Pages 1367-1370

  Djakovitch, Laurent ^a   Rollet, Patrick ^a  

^a INST DE RECHERCHES SUR LA CATALYSE   (France)

Author keywords

Copper free Sonogashira reaction; Heterogeneous catalysis; Palladium modified zeolite

Indexed keywords

ALKYNE; BROMINE DERIVATIVE; COPPER; HALIDE; IODINE DERIVATIVE; PALLADIUM; ZEOLITE;

ARTICLE; CATALYSIS; CATALYST; QUANTITATIVE ANALYSIS; SONOGASHIRA REACTION; SUBSTITUTION REACTION;

EID: 1642578978     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.077     Document Type: Article

References (52)

1. Moore J.S. Acc. Chem. Res. 30:1997;402. and references cited therein.
2. Hiyama T. Diederich F., Stang P.J. Metal-Catalyzed Cross-Coupling Reactions. 1998;Wiley-VCH, Weinheim. Chapter 10 and references cited therein.
3. Sonogashira K. J. Organomet. Chem. 653:2002;46.
4. Sonogashira K. Negishi E. Handbook of Organopalladium Chemistry for Organic Synthesis. 2002;Wiley-VCH, New York.
5. Tykwinski R.R. Angew. Chem., Int. Ed. 42:2003;1566.
6. Negishi E.-J., Anastasia L. Chem. Rev. 103:2003;1979.
7. Stang P.J., Diederich F. Modern Acetylene Chemistry. 1995;VCH, Weinheim.
8. Astruc D. Modern Arene Chemistry. 2002;Wiley-VCH, Weinheim.
9. Brandsma L., Vasilevsky S.F., Verkruijsse H.D. Applications of Transition Metal Catalysts in Organic Synthesis. 1988;Springer, Berlin. Chapter 10, pp 179-225.
10. Nicolaou K.C., Sorensen E.J. Classics in Total Synthesis. 1996;Wiley-VCH, Weinheim. pp 582.
11. Graham A.E., McKerrecher D., Davies D.H., Taylor R.J.K. Tetrahedron Lett. 37:1996;7445.
12. Miller M.W., Johnson C.R. J. Org. Chem. 62:1997;1582.
13. Sakai A., Aoyama T., Shioiri T. Tetrahedron Lett. 40:1999;4211.
14. Yoshimura F., Kawata S., Hirama M. Tetrahedron Lett. 40:1999;8281.
15. Toyota M., Komori C., Ihara M. J. Org. Chem. 65:2000;7110.
16. Paterson I., Davies R.D.M., Marquez R. Angew. Chem., Int. Ed. 40:2001;603.
17. Uenishi J.-I., Matsui K., Ohmiya H. J. Organomet. Chem. 653:2002;141.
18. Sonogashira K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;521-549 Pergamon, New York.
19. Chow H.-F., Wan C.-W., Low K.-H., Yeung Y.-Y. J. Org. Chem. 66:2001;1910.
20. Casalnuovo A.L., Calabrese J.C. J. Am. Chem. Soc. 112:1990;4324.
21. Dibowski H., Schmidtchen F.P. Tetrahedron Lett. 39:1998;525.
22. Kabalka G.W., Wang L., Namboodiri V., Pagni R.M. Tetrahedron Lett. 41:2000;5151.
23. Bong D.T., Ghadiri M.R. Org. Lett. 3:2001;2509.
24. Mio M.J., Kopel L.C., Braun J.B., Gadzikwa T.L., Hull K.L., Brisbois R.G., Markworth C.J., Grieco P.A. Org. Lett. 4:2002;3199.
25. Remmele H., Köllhofer A., Plenio H. Organometallics. 22:2003;4098.
26. Fukuyama T., Shinmen M., Nishitani S., Sato M., Ryu I. Org. Lett. 4:2002;1691.
27. Okita T., Isobe M. Synlett. 1994;589.
28. Nguefack J.-F., Bolitt V., Sinou D. Tetrahedron Lett. 37:1996;5527.
29. Hundertmark T., Littke A.F., Buchwald S.L., Fu G.C. Org. Lett. 2:2000;1729.
30. Netherton M.R., Fu G.C. Org. Lett. 3:2001;4295.
31. Méry D., Heuzé K., Astruc D. Chem. Commun. 2003;1934.
32. Powell N.A., Rychnosky S.D. Tetrahedron Lett. 37:1996;7901.
33. Crisp G.T., Turner P.D., Stephens K.A. J. Organomet. Chem. 570:1998;219.
34. Nakamura K., Ohubo H., Yamaguchi M. Synlett. 1999;549.
35. Dai W.-M., Guo D.-S., Sun L.-P. Tetrahedron Lett. 42:2001;5275.
36. Siemsen P., Livingston R.C., Diederich F. Angew. Chem., Int. Ed. 39:2000;2632.
37. Genêt J.-P., Blart E., Savignac M. Synlett. 1992;715.
38. Alami M., Ferri F., Linstrumelle G. Tetrahedron Lett. 34:1993;6403.
39. Böhm V.P., Herrmann W.A. Eur. J. Org. Chem. 2000;3679.
40. Pal M., Parasuraman K., Gupta S., Yeleswarapu K.R. Synlett. 2002;1976.
41. Fu X., Zhang S., Yin Y., Schumacher D. Tetrahedron Lett. 43:2002;6673.
42. Alonso D.A., Nájera C., Pacheco C. Tetrahedron Lett. 43:2002;9365.
43. Alonso D.A., Nájera C., Pacheco M.C. Adv. Synth. Catal. 345:2003;1146.
44. Heuzé K., Méry D., Gauss D., Astruc D. Chem. Commun. 2003;2274.
45. Heidenreich R.G., Köhler K., Krauter J.G.E., Pietsch J. Synlett. 2002;1118.
46. Novák Z., Szabó A., Répási J., Kotschy A. J. Org. Chem. 68:2003;3327.
47. Djakovitch L., Köhler K. J. Mol. Catal. A: Chem. 142:1999;275.
48. Djakovitch L., Heise H., Köhler K. J. Organomet. Chem. 584:1999;16.
49. Djakovitch L., Köhler K. J. Am. Chem. Soc. 123:2001;5990.
50. Michalik J., Narayana M., Kevan L. J. Phys. Chem. 89:1985;4553.
51. Sachtler W.M.H., Cacalcanti F.A.P. Catal. Lett. 9:1991;261.
52. Streitwieser A., Heathcock C.K., Kosower E.M. Introduction to Organic Chemistry. 4th ed. 1992;MacMillan, London.