Conformational changes and anion-cation interactions in palladium-cyclometalated BINAP and chiraphos cationic complexes. A structural study via NMR and X-ray methods

Organometallics

Volumn 26, Issue 20, 2007, Pages 4942-4954

  Nama, Devendrababu ^a   Butti, Pietro ^a   Pregosin, Paul S ^a  

^a LABORATORY OF INORGANIC CHEMISTRY   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CHELATION; COMPLEXATION; CONFORMATIONS; NUCLEAR MAGNETIC RESONANCE; X RAY DIFFRACTION;

BINAP; CHIRAL CYCLOMETALATED AMINE CHELATE; CHIRAPHOS CATIONIC COMPLEXES; NMR OVERHAUSER MEASUREMENTS;

PALLADIUM COMPOUNDS;

EID: 34948887311     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700299b     Document Type: Article

References (75)

1. Helmchen, G.; Pfaltz, A. Ace Chem. Res. 2000. 33, 336-345.
2. Helmchen, G. J. Organomet. Chem. 1999, 576, 203-214.
3. Trost, B. M.; Fraisse, P. L.; Ball, Z. T. A. Angew. Chem., Int. Ed. 2003. 41, 1059-1061.
4. Trost, B. M.; Fraisse, P. L.; Ball, Z. T. Angew. Chem., Int. Ed. 2002, 41, 1059-1061.
5. Hermatschweiler, R.; Fernandez, I.; Breher, F.; Pregosin, P. S.; Veiros, L. F.; Calhorda. M. J. Angew. Chem., Int. Ed. 2005, 44, 4397-4400.
6. Gsponer, A.; Consiglio, G. Helv. Chim. Acta 2003, 86, 2170-2172.
7. Sirbu, D.; Consiglio, G.; Milani, B.; Kumar, P. G. A.; Pregosin, P. S.; Gischig, S. J. Organomet. Chem. 2005, 690, 2254-2262.
8. (a) Kundig, E. P.; Saudan, C. M.; Bernardinelli, G. H. Angew. Chem. 1999, 111, 1298-1301.
9. (b) Kumar, P. G. A.; Pregosin, P. S.; Vallet, M.; Bernardinelli, G.; Jazzar, R. F.; Viton, F.; Kundig, E. P. Organometallics 2004, 23, 5410-5418.
10. Smidt, S. P.; Zimmermann, N.; Studer. M.; Pfaltz, A. Chem. Eur. J. 2004, 10, 4685-4693.
11. Mazet, C.; Smiidt, S. P.; Meuwly, M.; Pfaltz, A. J. Am. Chem. Soc. 2004, 126, 14176-14181.
12. Mclntyre, S.; Hormann, E.; Menges, F.; Smidt, S. P.; Pfaltz. A. Adv. Synth. Catal. 2005, 347, 282-288.
13. Lautens, M.; Fagnou, K.; Yang, D. Q. J. Am. Chem. Soc. 2003, 125, 14884-14892.
14. Fagnou, K.; Lautens. M. Angew. Chem.. Int. Ed. 2002, 41, 27-47.
15. Krossing, I.; Raabe, I. Angew. Chem.. Int. Ed. 2004, 43, 2066-2090.
16. Lancaster, N. L.; Welton, T. J. Org. Chem. 2004, 69, 5986-5992.
17. Faller, J. W.; Fontaine, P. P. Organometallics 2005, 24, 4132-4138.
18. Semeril, D.; Bruneau. C.; Dixneuf, P. H. Adv. Synth. Catal. 2002, 344, 585-595.
19. Stahl, N. G.; Zuccaccia, C.; Jensen, T. R.; Marks. T. J. J. Am. Chem. Soc. 2003, 125, 5256-5257.
20. Zuccaccia, C.; Stahl, N. G.; Macchioni, A.; Chen, M. C.; Roberts, J. A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 1448-1464.
21. Chen, M. C.; Roberts, J. A. S.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 4605-4625.
22. Kumar, P. G. A.; Pregosin, P. S.; Schmid, T. M.; Consiglio, G. Magn. Reson. Chem. 2004, 42, 795-800.
23. Martinez-Viviente, E.; Pregosin, P. S. Inorg. Chem. 2003, 42, 22092214.
24. (a) Pregosin, P. S. Prog. Nucl. Magn. Reson. Spectrosc. 2006, 49, 261-288.
25. (b) Pregosin, P. S.; Kumar, P. G. A.; Fernandez, I. Chem. Rev. 2005, 105, 2977-2998.
26. (c) Pregosin, P. S.; Martinez-Viviente, E.; Kumar, P. G. A. Dalton Trans. 2003, 4007-4014.
27. (a) Pettinari, C.; Pettinari, R.; Marchetti, F.; Macchioni, A.; Zuccaccia, D.; Skelton, B. W.; White, A. H. Inorg. Chem. 2007, 46, 896-906.
28. (b) Ciancaleoni, G.; Di Maio, I.; Zuccaccia, D.; Macchioni, A. Organometallics 2007, 26,489-496.
29. (c) Zuccaccia, D.; Busetto, L.; Cassani, M. C.; Macchioni, A.; Mazzoni, R. Organometallics 2006, 25, 2201 -2208.
30. (d) Zuccaccia, D.; Bellachioma, G.; Cardaci, G.; Zuccaccia, C.; Macchioni, A. Dalton Trans. 2006, 1963-1971.
31. (e) Zuccaccia, C.; Bellachioma, G.; Cardaci, G.; Macchioni, A.; Binotti, B.; Carfagna, C. Helv. Chim. Acta 2006, 89, 1524-1546.
32. (f) Macchioni, A. Chem. Rev. 2005, 105, 2039-2073.
33. (g) Zuccaccia, C.; Macchioni, A.; Orabona, I.; Ruffo, F. Organometallics 1999, 18, 4367-4372 and references therein.
34. Keresztes, I.; Williard, P. G. J. Am. Chem. Soc. 2000, 122, 10228-10229.
35. Branda, T.; Cabrita, E. J.; Berger, S. Prog. Nucl. Magn. Reson. Spectrosc. 2005, 46, 159-196.
36. Cohen, Y.; Avram, L.; Frish, L. Angew. Chem., Int. Ed. 2005, 44, 520-554.
37. Dehand, J.; Pfeffer, M. Cyclometallated Compounds. Coord. Chem. Rev. 1976, 18, 327-352.
38. Pfeffer, M.; Fischer, J.; Mitschier, A.; Ricard, L. J. Am. Chem. Soc. 1980, 102, 6338.
39. Pfeffer, M. Recl. Trav. Chim. PaysBas 1990, 109, 567 and references therein.
40. Ryabov, A. D. Chem. Rev. 1990, 90, 403.
41. Espinet, P.; Esteruelas, M. A.; Oro, L. A.; Serrano, J. L.; Sola, E. Coord. Chem. Rev. 1992, 15, 215 and references therein.
42. Li, Y.; Tan, G.-K.; Koh, L. L.; Vittal, J. J.; Leung, P. H. Inorg. Chem. 2005, 44, 9874-9886.
43. Albinati, A.; Affolter, S.; Pregosin, P. S. Organometallics 1990, 9, 379-387.
44. (a) Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245-1253.
45. (b) Lopez, C.; Bosque, R.; Sainz, D.; Solans, X.; Font-Bardia, M. Organometallics 1997, 16, 3261-3266.
46. (c) Roberts, N. K.; Wild, S. B. J. Am. Chem. Soc. 1979, 101, 6254.
47. Qin. Y.; Lang, H.; Vittal, J. J.; Tan, G.-K.; Selvaratnam, S.; White, A. J. P.; Williams, D. J.; Leung, P.-H. Organometallics 2003, 22, 3944-3950.
48. Kirsch, S. F.; Overman, L. E. J. Am. Chem. Soc. 2005, 127, 2866-2867.
49. Overman, L. E.; Remarchuk,. T. P. J. Am. Chem. Soc. 2002, 124, 12-13.
50. 13C NMR Data for Organometallic Compounds; Academic Press: London, 1981.
51. Tschoerner, M.; Kunz, R. W.; Pregosin, P. S. Magn. Reson. Chem. 1999, 37, 91-97.
52. Tschoerner, M.; Pregosin, P. S. Inorg. Chim. Acta 1999, 290, 95-99.
53. Martinez-Viviente, E.; Pregosin, P. S.; Tschoerner, M. Magn. Reson. Chem. 2000, 38, 23-28.
54. Orpen, A. G.; Brammer, L.; Allen, F. H.; Kennard, O.; Watson, D. G.; Taylor, R. J. Chem. Soc., Dalton Trans. 1989, S1-S83.
55. (a) Ohta, T. H. T.; Noyori, R. Inorg. Chem. 1988, 27, 566-569.
56. (b) Mashima, K.; Kusano, K.; Ohta, T.; Noyori, R.; Takaya, H. J. Chem. Soc., Chem. Commun. 1989, 1208.
57. (c) Pathak, D. D.; Adams, H.; Bailey, N. A.; King, P. J.; White, C. J. Organomet. Chem. 1994, 479, 237.
58. (d) Zhang, X.; Mashima, K.; Koyano, K.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Takaya, H. J. Chem. Soc., Perkin Trans. 1994, 2309-2322.
59. (e) Brown, J. M.; Torrente, J. J. P. Organometallics 1995, 14, 1195-1203.
60. (f) Wiles, J. A.; Lee, C. E.; McDonald, R.; Bergens, S., H. Organometallics 1996, 15, 3782-3784.
61. Ruegger, H.; Kunz, R. W.; Ammann, C. J.; Pregosin, P. S. Magn. Reson. Chem. 1991, 29, 197-203.
62. Ammann, C. J.; Pregosin, P. S.; Ruegger, H.; Albinati, A.; Lianza, F.; Kunz, R. W. J. Organomet. Chem. 1992, 423, 415-430.
63. Pregosin, P. S.; Ruegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 83-90.
64. Nama, D.; Schott, D.; Pregosin, P. S.; Veiros, L. F.; Calhorda, M. J. Organometallics 2006, 25, 4596-4604.
65. 4J(P,H) on the relative position of the NMe and NMe' groups. However, since the change from, for example, (R)-BINAP to (S)-BINAP changes the amine ring conformation and consequently the relative positions of these two NMe groups, in one diastereomer the NMe appears as a triplet whereas in the other diastereomer the NMe' is now the triplet.
66. Wiles, J. A.; Bergens, S. H. Organometallics 1999, 18, 3709-3714.
67. Drago, D.; Pregosin, P. S.; Tschoerner, M.; Albinati, A. J. Chem. Soe, Dalton Trans. 1999, 2279-2280.
68. Despite a significant spectroscopic effort, it was not possible to assign each BINAP proton unambiguously. Considerable overlap led to an element of uncertainty with respect to the HOESY contacts.
69. (41 ) McFarlane and co-workers (McFarlane, W.; Swarbrick, J. D.; Bookham, J. L. J. Chem. Soc. Dalton 1998, 3233-3238) report (almost) an average of the two conformations for this diastereomer. Our proton spectra and observed NOE results are in agreement with their data.
70. See also Jiang, O.; Ruegger, H.; Venanzi, L. M. J. Organomet. Chem. 1995, 488, 233-240, for related findings.
71. There is a very weak contact to the Chiraphos methyl groups. The chiral array does not show marked axial or equatorial P-phenyl groups.
72. This assumes (a) that other interactions are absent, e.g., hydrogen bonding, anion encapsulation, etc., which would result in restricted translation of the anion, and (b) that the two ions are markedly different in size.
73. H-ray
74. Albinati, A.; Pregosin, P. S.; Ruedi, R. Helv. Chim. Acta 1985, 68, 2046-2061.
75. ;(46) Cope, A. C.; Friedrich, E. C. J. Am. Chem. Soc. 1968, 90, 909.