Synthesis, characterization and dynamic behavior of (π-allyl)palladium complexes with polydentate nitrogen ligands, evidence of a dissociative mechanism

Chemische Berichte

Volumn 129, Issue 5, 1996, Pages 589-594

  Elguero, José ^a,b,c   Fruchier, Alain ^a,b   De La Hoz, Antonio ^a,b   Jalón, Félix A ^a,b   Manzao, Blanca R ^a,b   Oteroo, Antonio ^a,b   Torre, Felipe Gómez De La ^a,b  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b INSTITUT CHARLES GERHARDT   (France)

^c UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

Author keywords

Fluxionality; Heterocyclic ligands; Palladium complexes

Indexed keywords

EID: 0001437545     PISSN: 00092940     EISSN: None     Source Type: Journal    
DOI: 10.1002/cber.19961290519     Document Type: Article

References (61)

1. [1a] R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985.
2. [1b] J. Tsuji, Organic Synthesis with Palladium Compounds, Springer Verlag, New York, 1980.
3. [1c] J. P. Coalman, L. S. Hegedeus, J R. Norton, R. G. Finke, Principles and Applications uf Organotransition Metal Chemistry, University Science Books, 1987.
4. [1d] P. W. Jolly, Angew. Chem. Int. Ed. Engl. 1985, 24. 283-295.
5. [1e] B. M. Trost, T. R. Verhoeven, Comprehensive Organometcillic Chemistry, vol. 8 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pcrgamon Press, Oxford, 1982, pp. 799-938.
6. [1f] G. Consiglio. R. M. Waymounth. Chem. Rev. 1989, 89, 257.
7. [1g] M. Sawamara, H. Nagata, H. Sakamoto, Y. Ito. J. Am. Chem. Soc. 1992, 114, 2586-2592.
8. [2a] T. Hayashi in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH Publishers, New York, 1993, pp. 325-365 and references therein.
9. [2b] T. Hayashi, A. Yamamoto, Tetrahedron Lea. 1988, 29. 669.
10. [2c] T. Hayashi. A. Yamamoto. Y. Ito, E. Nishyoka, H. Miura, K. Yanagi, J. Am. Chem. Soc. 1989, 111, 6301-6311.
11. [2d] P. Matt, A. Pfaltz, Angew. Chem. Int. Ed Engl. 1993, 32, 566-568.
12. [2e] B. M. Trost. D. L. Van Vranken, C. Bingei, J. Am. Chem. Soc. 1992, 114, 9327-9343.
13. [2f] M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493-4506.
14. [3a] A. Albinati, C. J. Ammann, P. S. Pregosin, H. Rüegeer, Organometallics 1990, 9, 1826-1833.
15. [3b] A. Albinati, R. W. Kunz, C. J. Ammann, P. S. Pregosin, Organometallics 1991, 10, 1800-1806.
16. [41 [4a] K. Vrieze, p. W. N. m. van Lceuwen, Prag. Inorg.Chem. 1971, 14, 1-64 and references cited therein.
17. [4b] J. W. Faller, M. J. Incorvia, M. E. Thomsen, J. Am. Chem. Soc. 1969, 91, 518-519.
18. [4c] D. L. Tibbetts, T. L. Brown, J. Am. Chem. Soc. 1970, 92, 3031-3034.
19. [4e] A. Gogoil, H. Greenberg, Magn. Reson. Chem. 1993, 31, 954-959.
20. [4e] A. Gogoil, J. Ornebro, H. Grennberg, J. E. Bäckvall, J. Am. Chem. Soc. 1994, 116, 3631-3632.
21. [4f] D. G. Brown, P. K. Byers, A. J. Canty, Organometallics 1990, 9, 1231 - 1235.
22. [4g] A. J. Canty, H. Jin, A. S. Roberts- P. R. Traill, B. W. Skehon. A. H. White, J. Organomet. Chem. 1995, 489, 153-159.
23. [4h] C. Breutel, P. S. Pregosin, R. Salzmann, A. Togni, J. Am. Chem. Soc. 1994, 116, 4067-4068.
24. [4i] P. S. Pregosin. R. Salzmann, A. Togni, Organomemllics 1995, 14, 842-847.
25. [5a] R. Fernandez-Galán, B. R. Manzano, A. Otero, M. Lanfranchi, M. A. Pellinghelli, Inorg. Chem. 1994, 33, 2309-2312.
26. [5b] F. A. Jalón, B. R. Manzano, A. Otero, M. C. Rodriguez-Pérez, J. Organomet. Chem. 1995, 494, 179-185.
27. [5c] S. Trofimenko, J. Am. Chem. Soc. 1970, 92. 5118-5126.
28. J. A. Casares, S. Coco, P. Espinet, Y.-S. Lin, Organometallics 1995, 14, 3058-3067 and references therein.
29. [7a] P. J. Steel, E. C. Constable, J. Chem. Research (S) 1989, 189 (M) 1989, 1601-1611.
30. [7b] M. Bruix, J. de Mendoza, J. Elguero. Tetrahedron 1987, 43, 4663-4668.
31. [7c] P. J. Steel, E. C. Constable, J. Chem. Soc., Dalton Trans. 1990, 1389-1396.
32. H. Günther, NMR Spectroscopy, John Wiley & Sons, New York, 1980.
33. E. Breitmeier, W. Voelter, Carbon 13 NMR Spectroscopy. High Resolution Methods and Applications in Organic Chemistry and Biochemistry, 3rd ed., VCH, Weinheim. 1987.
34. J. Sandström, Dynamic NMR Spectroscopy, Academic Press. New York, 1982.
35. [11a] G. Binsch, J. Am. Chem. Soc. 1969, 91, 1304-1309.
36. [11b] D. A. Kleier. G. Binsen, J. Magn. Reson. 1970, 3, 146-160.
37. [12a] P. M. Maitlis, P. Espinet, M. J. H. Russell, in Comprehensive Organometallic Chemistry, G. Wilkinson, F. G. A. Stone and E. W. Abel, Eds.; Pergamo'n Press, Oxford, 1982, 6, 385-454.
38. [12b] K. Vrieze in Dynamic Nuclear Magnetic Resonance Spectroscopy, L. M. Jackman and F. A. Cotton, Eds. Academic Press, New York, 1975. pp. 441-487.
39. [13a] J. W. Faller, M. J. Incorvia, Inorg. Chem. 1968, 7, 840-842.
40. [13bl J. W. Faller, D. A. Haitko, J. Organomet. Chem. 1979, 149. C19-C23.
41. [13c] J. W. Faller, M. A. Adams, J. Organomet. Chem. 1979, 170, 71-80.
42. [13d] R. Benn, A. Rufinska, G. Schroth, J. Organomet. Ckem. 1981. 217, 91-104.
43. [13e] P. K. Baber, S. Clamp, N. G. Connelly. M. Murray, J. B. Sheridan, J. Chem. Soc. Chem. Commun. 1986, 459-460.
44. [13f] A. D. Horton, A. C. Kemball, M. J. Mays, J. Chem. Soc., Dalton Trans. 1988, 2953-2958.
45. [14) T. Bobchi, U. Belluco, T. Toniolo, R. Favez, R. Roulet. Inorg. Chim. Acta 1979, 23, 37.
46. [15a] B. Crociani, F. Di Bianca, A. Giovenco, T. Boschi, Inorg. Chim. Acta 1987, 127, 169.-182.
47. [15b] S. Hansson, P.-O. Norrby, M. P. T. Sjögren, B. Akerman, M. E. Cuccilito, F. Giorjuno, A. Vitagliano. Organometallics 1993, 12, 4940-4948.
48. J. W. Faller, M. J. Incorvia. J. Organomet. Chem. 1969, 19, P13-P16.
49. [16b] U. W. Faller, M. J. Mattina, Inorg. Chem. 1972, 11, 1296-1307.
50. C. Amman, P. S. Pregosin, H. Rueggcr. M. Grassi, A. Musco, Magn. Reson. Chem. 1989, 27, 355-359.
51. M. Grassi, S. V. Meille, A. Musco, R. Pontellini, A. Sironi, J. Chem. Soc., Dalton Trans. 1989, 615-621.
52. G. Hunter, A. McAuley, T. W. Whilcombe, Inorg. Chem. 1988, 27, 2634-2639.
53. [19b] S. Liu, C. R. Lucas, M. J. Newlands, J.-P. Charland. Inorg. Chem. 1990, 29, 4380-4385.
54. D. J. Mabbott, B. E. Mann, P. M. Maitlis, J. Chem. Soc., Dalton Trans. 1977, 294-299.
55. [21a] D. J. Thorn, R. Hoffmann, J. Am. Chem. Soc. 1978, 100, 2079-2090.
56. [21b] G. Alibrandi, L. M. Scolaro, R. Romeo, Inorg. Chem. 1991, 30, 4007-4013.
57. A. R. Katritzky Ed., Handbook of Heterocyclic Chemistry. Pergamon Press, Oxford 1985.
58. A. Loupy, N. Philippen, P. Pigeon, H. Galons, Heterocycles 1991, 32, 1947-1953.
59. M. A. Khan, J. B. Poyla, J. Chem. Soc. (C) 1970, 85-91.
60. [25a] W. T. Dent, R. Long, A. J. Wilkinson, J. Chem. Soc. 1964, 1585.
61. [25b] Y. Tatsuno, T. Yoshida. Inorg. Synth. 1979, 19, 220-221.