Palladium(0) complexes of a 15-membered macrocyclic triolefin as a recoverable catalyst - Monomer- and polystyrene-anchored versions

European Journal of Organic Chemistry

Volumn , Issue 2, 2000, Pages 239-243

  Cortés, Jordi ^a   Moreno Mañas, Marcial ^a   Pleixats, Roser ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

Catalysis; Cross coupling; Macrocycles; Palladium; Polymer

Indexed keywords

ALKENE; PALLADIUM COMPLEX; POLYSTYRENE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS;

EID: 0033984261     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200001)2000:2<239::aid-ejoc239>3.0.co;2-r     Document Type: Article

References (51)

1. For reviews see: [1a] J. Tsuji, Palladium Reagents and Catalysts: Innovations in Organic Synthesis, John Wiley and Sons, Chichester, 1995.
2. [1b] Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel, F. G. A. Stone, and G. Wilkinson), Pergamon Press, New York, 1995, vol. 12.
3. Transition Metals for Organic Synthesis (Eds.: M. Beller, and C. Bolm, C.), Wiley-VCH, Weinheim, 1998, vol. 1 and 2.
4. J. Tsuji, Synthesis 1990, 739-749.
5. J. L. Malleron, J.-C. Fiaud, J.-Y. Legros, Handbook of Palladium-Catalyzed Organic Reactions, Academic Press, San Diego, 1997.
6. J. Krause, K.-J. Haack, G. Cestaric, R. Goddard, K.-R. Pöischke, Chem. Commun. 1998, 1291-1292.
7. W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, 2256-2282; Angew. Chem. Int. Ed. Engl. 1997, 36, 2162-2187.
8. W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, 2256-2282; Angew. Chem. Int. Ed. Engl. 1997, 36, 2162-2187.
9. W. A. Herrmann, B. Cornils, Angew. Chem. 1997, 109, 1074-1095; Angew. Chem. Int. Ed. Engl. 1997, 36, 1048-1067.
10. W. A. Herrmann, B. Cornils, Angew. Chem. 1997, 109, 1074-1095; Angew. Chem. Int. Ed. Engl. 1997, 36, 1048-1067.
11. Applied Homogeneous Catalysis with Organometallic Compounds (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996, vol. 1 and 2.
12. Aqueous-Phase Organometallic Catalysis (Eds.: B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 1998.
13. For general reviews see: [10a] P. Panster, S. Wieland, Immobilization, in ref.[8] Chapter 3.1.1.3, pages 605-623.
14. [10b] P. Kalck, M. Dessoudeix, Ligands or Complexes Containing Ancillary Functionalities, in ref.[9] Chapter 3.2.3, pages 105-122.
15. For a review on the use of immobilized metallic catalysts in inorganic solids see: J. H. Clark, D. J. Macquarrie, Chem. Commun. 1998, 853-860.
16. W. A. Herrmann, C. W. Kohlpaintner, Angew. Chem. 1993, 105, 1588; Angew. Chem. Int. Ed. Engl. 1993, 32, 1524-1544.
17. W. A. Herrmann, C. W. Kohlpaintner, Angew. Chem. 1993, 105, 1588; Angew. Chem. Int. Ed. Engl. 1993, 32, 1524-1544.
18. B. Cornils, W. A. Herrmann, Homogeneous Catalysts and Their Heterogenization or Immobilization. In ref.[8] Chapter 3.1.1, pages 575-601.
19. [14a] F. Joó, A. Kathó, J. Mol. Catal. (A) 1997, 116, 3-26.
20. [14b] B. Cornils, W. A. Herrmann, R. W. Eckl, J. Mol. Catal. (A) 1997, 116, 27-33.
21. For reviews see: [15a] I. T. Horváth, Heterogenization by Other Immiscible Phases. In ref. 8. Chapter 3.1.1.2, pages 601-605.
22. [15b] B. Cornils, Angew. Chem. 1997, 109, 2147-2149; Angew. Chem. Int. Ed. Engl. 1997, 36, 2057-2059.
23. [15b] B. Cornils, Angew. Chem. 1997, 109, 2147-2149; Angew. Chem. Int. Ed. Engl. 1997, 36, 2057-2059.
24. [15c] I. T. Horváth, Acc. Chem. Res. 1998, 31, 641-650.
25. [16a] S.-B. Jang, Tetrahedron Lett. 1997, 38, 1793-1796.
26. [6b] I. Fenger, C. Le Drian, Tetrahedron Lett. 1998, 39, 4287-4290.
27. M. Terasawa, K. Kaneda, T. Imanaka, S. Teranishi, J. Organometal. Chem. 1978, 162, 403-414.
28. D. E. Bergbreiter, Y.-S. Liu, Tetrahedron Lett. 1997, 38, 7843-7846.
29. [19a] C.-M. Andersson, K. Karabelas, A. Hallberg, C. Andersson, J. Org. Chem. 1985, 50, 3891-3895.
30. [19b] Z. Zhuangyu, P. Yi, H. Hongwen, K. Tsi-yu, Synth. Commun. 1990, 20, 3563-3574.
31. [19c] Z. Zhuangyu, P. Yi, H. Honwen, K. Tsiyu, Synthesis 1991, 539-542.
32. [19d] L. Yi, Z. Zhuangyu, H. Hongwen, Synth. Commun. 1995, 25, 595-601.
33. [19e] S.-B. Jang, Tetrahedron Lett. 1997, 38, 4421-4424.
34. [20a] B. M. Trost, E. Keinan, J. Am. Chem. Soc. 1978, 100, 7779-7781.
35. [20b] B. M. Trost, R. W. Warner, J. Am. Chem. Soc. 1982, 104, 6112-6114.
36. [20c] D. E. Bergbreiter, B. Chen. T. J. Lynch, J. Org. Chem. 1983, 48, 4179-4186.
37. [20d] B. M. Trost, R. W. Warner, J. Am. Chem. Soc. 1983, 105, 5940-5492.
38. [20e] D. E. Bergbreiter, D. A. Weatherford, J. Org. Chem. 1989, 54, 2726-2730.
39. [20f] D. E. Bergbreiter, B. Chen, D. Weatherford, J. Mol. Catal. 1992, 74, 409-419.
40. [20g] D. E. Bergbreiter, Y.-S. Liu, P. L. Osburn, J. Am. Chem. Soc. 1998, 120, 4250-4251.
41. [21a] C. U. Pittman, Jr., Q. Ng, J. Organometal. Chem. 1978, 153, 85-97.
42. [21b] K. Kaneda, H. Kurosaki, M. Terasawa, T. Imanaka, S. Teranishi, J. Org. Chem. 1981, 46, 2356-2362.
43. [21c] F. Benvenuti, C. Carlini, A. M. Raspolli Galleti, G. Sbrana, M. Marchionna, R. Patrini, J. Mol. Catal. (A) 1999, 137, 49-63.
44. S. Cerezo, J. Cortés, J.-M. López-Romero, M. Moreno-Mañas, T. Parella, R. Pleixats, A. Roglans, Tetrahedron 1998, 54, 14885-14904.
45. S. Itsuno, Y. Sakurai, K. Ito, T. Maruyama, S. Nakahama, J. M. J. Fréchet, J. Org. Chem. 1990, 55, 304-310.
46. Elemental analysis of 13 indicated full integration of all three monomers into the polymer, and elemental analysis of 14 indicated full incorporation of palladium. From this data, 0.5 miliequiv. of palladium per gram of polymer 14 has been estimated.
47. M. Moreno-Mañas, F. Pajuelo, R. Pleixats, J. Org. Chem. 1995, 60, 2396-2397.
48. T. I. Wallow, B. M. Novak, J. Org. Chem. 1994, 59, 5034-5037.
49. A. Feigenbaum, J.-M. Lehn, Bull. Soc. Chim. Fr. 1973, 198-202.
50. R. H. Wiley, J. M. Schmitt, J. Am. Chem. Soc. 1956, 78, 2169-2171.
51. E. I. Negishi, A. O. King, N. Okukado, J. Org. Chem. 1977, 42, 1821-1823.