Effect of correl cavities associated with molecularly imprinted platinum centers on the selectivity of ligand-exchange reactions at platinum

Journal of the American Chemical Society

Volumn 122, Issue 26, 2000, Pages 6217-6225

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

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE GLYCOL; LIGAND; METHACRYLIC ACID; PLATINUM COMPLEX;

ARTICLE; BINDING SITE; CATALYSIS; CHIRAL CHROMATOGRAPHY; CHIRALITY; CROSS LINKING; ENANTIOMER; LIGAND BINDING; POLYMERIZATION; REACTION ANALYSIS; STOICHIOMETRY; TEMPERATURE;

EID: 0034608963     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000462c     Document Type: Article

References (65)

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5. Selected examples: (a) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed; VCH Publishers: Mew York, 1993; pp 325-365. (b) Sawarnura, M.; Ito, Y. In Catalytic Asyminetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York. 1993; pp 367-388. (c) Sawamura, M.; Nagata, H.; Sakamoto, H.; Ito, Y. J. Am. Ckem. Soc. 1992, 114, 2586-2592. (d) Armspach, D.; Matt, D. Chem. Commun. 1999, 1073-1074. (e) Collman, J. P.; Zhang, X.; Lee, V. J.; Uffelman, E. S.; Brauman, J. I. Science 1993, 261, 1404-1411. (f) Sanders, J. K. M. Chem. Eur. J. 1998, 4, 1378-1383.
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29. Supporting Information from: Sasai, H.; Tokunaga, T.; Watanabe, S.; Suzuki, T.; Itoh, N.; Shibasaki, M. J. Org. Chem. 1995, 60, 7388-7389.
30. Full details of syntheses of 1 and precursors are given in the Supporting Information.
31. The MIP particles used in experiments were ≤2 mm/edge but were not of uniform size. To minimize loss of material, sieving was not performed.
32. 2 adsorption isotherms by application of the BET theory (see Experimental Section). Average pore diameter was 45 Å; pore volume distribution measurements showed that the majority of pores have diameters less than 100 Å and can thus be classified as micro- (<20 Å diameter) or mesopores (20-500 Å diameter).
33. 2 complexes immobilized in polymers with cross-link densities of ≤50% give resonances with narrow (100 Hz) line widths. See: (a) Fyfe, C. A.; Clark, H. C.; Davies, J. A.; Hayes, P. J.; Wasylishen, R. E. J. Am. Chem. Soc. 1983, 105, 6577-6584. (b) Bemi, L.; Clark, H. C.; Fyfe, C. A.; Wasylishen, R. E. J. Am. Chem. Soc. 1982, 104, 438-445.
34. 2 complexes immobilized in polymers with cross-link densities of ≤50% give resonances with narrow (100 Hz) line widths. See: (a) Fyfe, C. A.; Clark, H. C.; Davies, J. A.; Hayes, P. J.; Wasylishen, R. E. J. Am. Chem. Soc. 1983, 105, 6577-6584. (b) Bemi, L.; Clark, H. C.; Fyfe, C. A.; Wasylishen, R. E. J. Am. Chem. Soc. 1982, 104, 438-445.
35. 13C CP/MAS data for MIPs has, however, been obtained by Shea. See: Shea, K. J.; Sasaki, D. Y. J. Am. Chem. Soc. 1991, 113, 4109-4120.
36. eq) depends largely on the relative acidities of the ligands involved: coordination of strongly acidic ligands to Pt is favored over coordination of less acidic ones (manuscript in progress). For a careful analysis of the kinetics of this phenomenon see: Simpson, R. D.; Bergman, R. G. Organometallics 1993, 12, 781-796.
37. 31P NMR spectra of (dppe)Pt[(R)-BINOL] show that the complex's chemical shift depends on the amount of free BINOL present in solution, suggesting that H-bonding is occurring. See: (a) Andrews, M. A.; Cook, G. K.; Shriver, Z. H. Inorg. Chem. 1997, 36, 5832-5844. (b) Kim, Y.-J.; Osakada, K.; Takenaka, A.; Yamamoto, A. J. Am. Chem. Soc. 1990, 112, 1096-1104. (c) Kegley, S. E.; Schaverien, C. J.; Freudenberger, J. H.; Bergman, R. G.; Nolan, S. P.; Hoff, C. D. J. Am. Chem. Soc. 1987, 109, 6563-6565. (d) Bugno, C. D.; Pasquali, M.; Leoni, P.; Sabatino, P.; Braga, D. Inorg. Chem. 1989, 28, 1390-1394. (e) See ref 17.
38. 31P NMR spectra of (dppe)Pt[(R)-BINOL] show that the complex's chemical shift depends on the amount of free BINOL present in solution, suggesting that H-bonding is occurring. See: (a) Andrews, M. A.; Cook, G. K.; Shriver, Z. H. Inorg. Chem. 1997, 36, 5832-5844. (b) Kim, Y.-J.; Osakada, K.; Takenaka, A.; Yamamoto, A. J. Am. Chem. Soc. 1990, 112, 1096-1104. (c) Kegley, S. E.; Schaverien, C. J.; Freudenberger, J. H.; Bergman, R. G.; Nolan, S. P.; Hoff, C. D. J. Am. Chem. Soc. 1987, 109, 6563-6565. (d) Bugno, C. D.; Pasquali, M.; Leoni, P.; Sabatino, P.; Braga, D. Inorg. Chem. 1989, 28, 1390-1394. (e) See ref 17.
39. 31P NMR spectra of (dppe)Pt[(R)-BINOL] show that the complex's chemical shift depends on the amount of free BINOL present in solution, suggesting that H-bonding is occurring. See: (a) Andrews, M. A.; Cook, G. K.; Shriver, Z. H. Inorg. Chem. 1997, 36, 5832-5844. (b) Kim, Y.-J.; Osakada, K.; Takenaka, A.; Yamamoto, A. J. Am. Chem. Soc. 1990, 112, 1096-1104. (c) Kegley, S. E.; Schaverien, C. J.; Freudenberger, J. H.; Bergman, R. G.; Nolan, S. P.; Hoff, C. D. J. Am. Chem. Soc. 1987, 109, 6563-6565. (d) Bugno, C. D.; Pasquali, M.; Leoni, P.; Sabatino, P.; Braga, D. Inorg. Chem. 1989, 28, 1390-1394. (e) See ref 17.
40. 31P NMR spectra of (dppe)Pt[(R)-BINOL] show that the complex's chemical shift depends on the amount of free BINOL present in solution, suggesting that H-bonding is occurring. See: (a) Andrews, M. A.; Cook, G. K.; Shriver, Z. H. Inorg. Chem. 1997, 36, 5832-5844. (b) Kim, Y.-J.; Osakada, K.; Takenaka, A.; Yamamoto, A. J. Am. Chem. Soc. 1990, 112, 1096-1104. (c) Kegley, S. E.; Schaverien, C. J.; Freudenberger, J. H.; Bergman, R. G.; Nolan, S. P.; Hoff, C. D. J. Am. Chem. Soc. 1987, 109, 6563-6565. (d) Bugno, C. D.; Pasquali, M.; Leoni, P.; Sabatino, P.; Braga, D. Inorg. Chem. 1989, 28, 1390-1394. (e) See ref 17.
41. 31P NMR spectra of (dppe)Pt[(R)-BINOL] show that the complex's chemical shift depends on the amount of free BINOL present in solution, suggesting that H-bonding is occurring. See: (a) Andrews, M. A.; Cook, G. K.; Shriver, Z. H. Inorg. Chem. 1997, 36, 5832-5844. (b) Kim, Y.-J.; Osakada, K.; Takenaka, A.; Yamamoto, A. J. Am. Chem. Soc. 1990, 112, 1096-1104. (c) Kegley, S. E.; Schaverien, C. J.; Freudenberger, J. H.; Bergman, R. G.; Nolan, S. P.; Hoff, C. D. J. Am. Chem. Soc. 1987, 109, 6563-6565. (d) Bugno, C. D.; Pasquali, M.; Leoni, P.; Sabatino, P.; Braga, D. Inorg. Chem. 1989, 28, 1390-1394. (e) See ref 17.
42. 2 for 24 h.
43. 2BINOL MIPs except for opposite percent ee.
44. These reaction conditions include rebinding time (section 4), rebinding temperature (section 5), and rebinding solvent [not addressed here because preliminary experiments indicate that solvent effects on the rebinding reaction (Scheme 3) are small]. Note, however, that MIPs used as Chromatographic stationary phases often exhibit decreased selectivity when solvents other than the porogen used to prepare the MIP are employed as the mobile phase: (a) Spivak, D.; Gilmore, M. A.; Shea, K. J. J. Am. Chem. Soc. 1997, 119, 4388-4393. (b) Allender, C. J.; Heard, C. M.; Brain, K. R. Chirality 1997, 9, 238-242. Also, when rebinding occurs via hydrogen bonding of the template to the MIP, solvent polarity greatly affects rebinding selectivity. See refs 2 and 3.
45. These reaction conditions include rebinding time (section 4), rebinding temperature (section 5), and rebinding solvent [not addressed here because preliminary experiments indicate that solvent effects on the rebinding reaction (Scheme 3) are small]. Note, however, that MIPs used as Chromatographic stationary phases often exhibit decreased selectivity when solvents other than the porogen used to prepare the MIP are employed as the mobile phase: (a) Spivak, D.; Gilmore, M. A.; Shea, K. J. J. Am. Chem. Soc. 1997, 119, 4388-4393. (b) Allender, C. J.; Heard, C. M.; Brain, K. R. Chirality 1997, 9, 238-242. Also, when rebinding occurs via hydrogen bonding of the template to the MIP, solvent polarity greatly affects rebinding selectivity. See refs 2 and 3.
46. (a) Wulff, G.; Grobe-Einsler, R.; Vesper, W.; Sarhan, A. Makromol. Chem. 1977, 178, 2817-2825.
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48. (c) Shea, K. J.; Sasaki, D. Y. J. Am. Chem. Soc. 1991, 113, 4109-4120.
49. A similar situation was observed in ref 22b.
50. eq = 720 for the solution exchange reaction (manuscript in progress).
51. 2BINOL generally occupies 31% of the total Pt sites in P5 with 36 ± 1% ee.
52. The selectivity of other MIPs has been observed to increase with temperature in both batch rebinding and chromatographic experiments, see for example: (a) Wulff, G.; Vietmeier, J.; Poll, H.-G. Makromol. Chem. 1987, 188, 731-740. (b) Wulff, G.; Schauhoff, S. J. Org. Chem. 1991, 56, 395-400. (c) Wulff, G.; Poll, H.-G.; Minárik, M. J. Liq. Chromatogr. 1986, 9, 385-405. (d) Sellergren, B. Makromol. Chem. 1989, 190, 2703-2711.
53. The selectivity of other MIPs has been observed to increase with temperature in both batch rebinding and chromatographic experiments, see for example: (a) Wulff, G.; Vietmeier, J.; Poll, H.-G. Makromol. Chem. 1987, 188, 731-740. (b) Wulff, G.; Schauhoff, S. J. Org. Chem. 1991, 56, 395-400. (c) Wulff, G.; Poll, H.-G.; Minárik, M. J. Liq. Chromatogr. 1986, 9, 385-405. (d) Sellergren, B. Makromol. Chem. 1989, 190, 2703-2711.
54. The selectivity of other MIPs has been observed to increase with temperature in both batch rebinding and chromatographic experiments, see for example: (a) Wulff, G.; Vietmeier, J.; Poll, H.-G. Makromol. Chem. 1987, 188, 731-740. (b) Wulff, G.; Schauhoff, S. J. Org. Chem. 1991, 56, 395-400. (c) Wulff, G.; Poll, H.-G.; Minárik, M. J. Liq. Chromatogr. 1986, 9, 385-405. (d) Sellergren, B. Makromol. Chem. 1989, 190, 2703-2711.
55. The selectivity of other MIPs has been observed to increase with temperature in both batch rebinding and chromatographic experiments, see for example: (a) Wulff, G.; Vietmeier, J.; Poll, H.-G. Makromol. Chem. 1987, 188, 731-740. (b) Wulff, G.; Schauhoff, S. J. Org. Chem. 1991, 56, 395-400. (c) Wulff, G.; Poll, H.-G.; Minárik, M. J. Liq. Chromatogr. 1986, 9, 385-405. (d) Sellergren, B. Makromol. Chem. 1989, 190, 2703-2711.
56. 2BINOL could all be separated on a Daicel OD-H chiral column with 5%EtOH/ hexanes mobile phase. See Supporting Information for a typical chromatogram.
57. For an exception in which an MIP containing one functional group per cavity gave rise to a similar trend (selectivity increases with reactivity), see ref 22b.
58. Brunkan, N. M.; White, P. S.; Gagné, M. R. Angew. Chem., Int. Ed. 1998, 37, 1579-1582.
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60. 2 at room temperature. See ref 29.
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63. Barret, E. P.; Joyner, L. G.; Halenda, P. P. J. Am. Chem. Soc. 1951, 73, 373-380.
64. 2O was added to all MIP ligand-exchange reactions to ensure that they were performed under identical, water-saturated conditions.
65. This polymer was dried at 150 °C to remove all traces of PhCI before elemental analysis. All other polymers used in rebinding experiments were dried at room temperature.