NMR structure of an unusual Pt2(μ-BINOL) dimer: More surprises from a seemingly simple chiral ligand

Organometallics

Volumn 21, Issue 22, 2002, Pages 4711-4717

  Brunkan, Nicole M ^a   Gagné, Michel R ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS;

CHEMICAL BONDS; DIMERS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLATINUM COMPOUNDS;

ORGANOMETALLICS;

EID: 0037899158     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0204888     Document Type: Article

References (59)

1. (a) Ghosh, A. K; Matsuda, H. Org. Lett. 1999, 1, 2157-2159.
2. (b) Pignat, K.; Vallotto, J.; Pinna, F.; Strukul, G. Organometatlics 2000, 19, 5160-5167.
3. (c) Hao, J.; Hatano, M.; Mikami, K. Org. Lett. 2000, 2, 4059-4062.
4. (d) Oi, S.; Terada, E.; Ohuohi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1899, 64, 8660-8667, and refs 12, 13 therein.
5. (e) Hattori, T.; Suzuki, Y.; Uesugi, O.; Oi, S.; Miyana, S. Chem. Commun. 2000, 73-74.
6. (f) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548-4549.
7. (g) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017 - 5023.
8. (h) Hori, K.; Ito, J.; Ohta, T.; Furukawa, I. Tetrahedron 1998, 54, 12737-12744.
9. (i) Fürstner, A.; Voigtländer, D.; Schrader, W.; Giebel, D.; Reetz, M. T. Org. Lett. 2001, 3, 417-420.
10. (a) Brunkan, N. M.; White, P. S.; Gagné, M. R. Organometalics 2002, 21, 1565-1575.
11. (b) Brunkan, N. M.; Gagné, M. R. Organometallics 2002, 21, 1576-1582.
12. Pearson, R. G. Hard and Soft Acids and Bases; Dowden, Hutchinson, and Ross: Stroudsburg, PA, 1973.
13. (a) Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450-5458.
14. (b) Fujii, A.; Sodeoka, M. Tetrahedron Lett. 1999, 40, 8011-8014.
15. (c) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032-10039.
16. Brunkan, N. M.; White, P. S.; Gagné, M. R. J. Am. Chem. Soc. 1998, 120, 11002-11003.
17. Bergens, S. H.; Leung, P.-h.; Bosnich, B. Organometallics 1990, 9, 2406-2408.
18. Kočovský, P.; Vyskočil, S.; Císařová, I.; Sejbal, J.; Tišlerová, I.; Smrčina, M.; Lloyd-Jones, G. C.; Stephen, S. C.; Butts, C. P.; Murray, M.; Langer, V. J. Am. Chem. Soc. 1999, 121, 7714-7715.
19. (a) Kyba, E. P.; Gokel, G. W.; de Jonge, F.; Koga, K.; Sousa, L. R.; Siegel, M. G.; Kaplan, L.; Sogah, G. D. Y.; Cram, D. J. J. Org. Chem. 1977, 42, 4174.
20. (b) Wenkert, E.; Youssefyeh, R. D.; Lewis, R. G. J. Am. Chem. Soc. 1960, 82, 4675-4680.
21. (c) Kasturi, T. R.; Rajasekhar, B.; Raju, G. J.; Sivaramakrishnan, R.; Ramasubbu, N.; Venkatesan, K. J. Chem. Soc., Chem. Commun. 1980, 1087 - 1088.
22. (d) Georghiou, P. E.; Ashram, M.; Clase, H. J.; Bridson, J. N. J. Org. Chem. 1998, 63, 1819-1826.
23. (a) Bandini, A. L.; Banditelli, G.; Demartin, F.; Manassero, M. Minghetti, G. Gazz. Chim. Ital. 1993, 123, 417-423.
24. (b) Li, J. J.; Li, W.; Sharp, P. R. Inorg. Chem. 1996, 35, 604-613.
25. (c) Scarcia, V.; Furlni, A.; Longato, B.; Corain, B.; Pilloni, G. Inorg. Chim. Acta 1988, 153, 67-70.
26. 3 and 1 equiv of HOTf yielded pure material, uncontaminated by free BINOL (the byproduct when B forms from A), which was isolated as a white, air-and moisture-stable solid for characterization purposes.
27. 2 and AgOTf, was always removed from the reaction mixture by filtration before 1 was added to 2 to avoid decomposition of solutions of A generated by this route (solutions turned brown and precipitate formed if AgCl was present).
28. 31P NMR spectra of these reactions, even before decomposition was evidenced by color changes and precipitate formation.
29. (a) Pidcock, A.; Richards, R. E.; Venanzi, L. M. J. Chem. Soc. A 1966, 1707-1710.
30. (b) Appleton, T. G.; Bennett, M. A. Inorg. Chem. 1978, 17, 738-747.
31. Gugger, P.; Limmer, S. O.; Watson, A. A.; Willis, A. C.; Wild, S. B. Inorg. Chem. 1993, 32, 5692-5696.
32. Kégl, T.; Kollár, L,; Szalontai, G.; Kuzmann, E.; Vértes, A. J. Organomet. Chem. 1996, 507, 75-80.
33. (a) Feiken, N.; Pregosin, P. S.; Trabesinger, G. Organometallics 1997, 16, 537-543.
34. (b) Feiken, N.; Pregosin, P. S.; Trabesinger, G. Organometallics 1997, 16, 5756-5762.
35. (c) Pregosin, P. S.; Trabesinger, G. J. Chem. Soc., Dalton Trans. 1998, 727-734.
36. (d) den Rerjer, C. J.; Wörle, M.; Pregosin, P. S. Organometallics 2000, 19, 309-316.
37. (e) den Reger, C. J.; Drago, D.; Pregosin, P. S. Organometallics 2001, 20, 2982 -2989.
38. (f) den Reijer, C. J.; Dotta, P.; Pregosin, P. S.; Albinati, A. Can. J. Chem. 2001, 79, 693-704.
39. Coordination of BINAP to Ru by an aryl double bond: (a) Pathak, D. D.; Adams, H.; Bailey, N. A.; King, P. J.; White, C. J. Organomet. Chem. 1994, 479, 237-245.
40. (b) Wiles, J. A.; Bergens, S. H.; Vanhessche, K. P. M.; Dobbs, D. A.; Rautenstrauch, V. Angew. Chem., Int. Ed. 2001, 40, 914-919.
41. 3 to Mo or Ru by an aryl double bond: (c) Cheung, T.-Y.; Szalda, D. J.; Bullock, R. M. Chem. Commun. 1999, 1629-1630.
42. (d) Aneetha, H.; Jiménez-Tenorio, M.; Puerta, M. C.; Valerga, P.; Mereiter, K. Organometallics 2002, 21, 628-635.
43. 1H NMR data for these structures are expected to be similar.
44. Cross, R. J.; Davidson, M. F. J. Chem. Soc., Dalton Trans. 1987, 139-143.
45. 13C spectra proved more tractable.
46. Brunkan, N. M.; White, P. S.; Gagń, M. R. Angew. Chem., Int. Ed. 1998, 37, 1579-1582.
47. Only BINOL data are given in Figure 2. See Supporting Information for dppe data.
48. 31P-decoupled spectra.
49. See the Supporting Information from ref 5.
50. 2 and 2 were unsuccessful (vide infra).
51. 2a
52. 2 dimer has been reported: Ruiz, J.; Marti, J. M.; Florenciano, F.; López, G. Polyhedron 1999, 18, 2281-2285.
53. 1-coordination of the C=O group to Pt in 9 would yield a sterically strained four-membered chelate ring, rather than the five-membered chelate of A.
54. 2
55. Cai, D.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7991-7994. Also, note that using rac-BINOL rather than S-BINOL for the experiments described in this paper gave identical results.
56. Andrews, M. A.; Gould, G. L.; Klooster, W. T.; Koenig, K. S.; Voss, E. J. Inorg. Chem. 1996, 35, 5478 -5483.
57. See the Supporting Information from ref 2a.
58. 2.
59. Reference 2a contains NMR data for these complexes.