31P NMR and IR characterization of enantioselective olefin and arene hydrogenation catalysts containing a rhodium-chiral phosphine complex tethered on silica

Journal of Molecular Catalysis A: Chemical

Volumn 195, Issue 1-2, 2003, Pages 63-82

  Stanger, Keith J ^a   Wiench, Jerzy W ^a   Pruski, Marek ^a   Angelici, Robert J ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Arene hydrogenation; Enantioselective olefin hydrogenation; Immobilized metal catalysts; Palladium; Rhodium; Silica; Solid state 31P NMR

Indexed keywords

COMPLEXATION; COMPOSITION; HYDROGENATION; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; ORGANOMETALLICS;

LIGANDS;

CATALYSTS;

4 (DIPHENYLPHOSPHINO) 2 (DIPHENYLPHOSPHINOMETHYL)PYRROLIDINE; ALKENE; CARBON MONOXIDE; CINNAMIC ACID DERIVATIVE; METAL COMPLEX; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; PYRROLIDINE DERIVATIVE; RHODIUM COMPLEX; SILICON DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; HYDROGENATION; INFRARED SPECTROSCOPY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; SOLID STATE; SYNTHESIS;

EID: 0037452860     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1169(02)00572-1     Document Type: Article

References (44)

1. J.D. Morrison (Ed.), Asymmetric Synthesis, vol. 5, Chiral Catalysis, Academic Press, Orlando, 1985.
2. D.E. Vos, I.F.J. Vankelecom, P.A. Jacobs (Eds.), Chiral Catalyst Immobilization and Recycling, Wiley, New York, 2000.
3. E.N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Comprehensive Asymmetric Catalysis, vols. 1 and 3, Springer, New York, 1999.
4. M.J. Burk, F. Bienewald, Transition Met. Org. Synth. 2 (1998) 13.
5. B. Pugin, M. Müller, in: M. Guisnet, et. al. (Eds.), Stud. Surf. Sci. Cat. Part 78: Heterogeneous Catalysis and Fine Chemicals III, Elsevier, 1993, p. 107.
6. B. Pugin, J. Mol. Catal. A: Chem. 107 (1996) 273.
7. H. Gao, R.J. Angelici, J. Mol. Catal. A: Chem. 149 (1999) 63.
8. H. Gao, R.J. Angelici, J. Am. Chem. Soc. 119 (1997) 6937.
9. H. Gao, R.J. Angelici, Organometallics 18 (1999) 989.
10. H. Gao, R.J. Angelici, New J. Chem. 23 (1999) 633.
11. H. Yang, H. Gao, R.J. Angelici, Organometallics 19 (2000) 622.
12. A.B. Pangbom, M.A. Giardello, R.H. Grubbs, R.K. Rosen, F.J. Timmers, Oganometallics 15 (1996) 1518.
13. D.D. Perrin, W.L.F. Armarego, D.R. Perrin, Purification of Laboratory Chemicals, 2nd ed., Pergamon Press, New York, 1980.
14. J. Suh, E. Lee, Y.C. Myoung, M. Kim, S. Kim, J. Org. Chem. 50 (1985) 977.
15. R.M. Herbst, D. Shemin, in: A.H. Blatt (Ed.), Organic Syntheses, Collect. vol. 2, Wiley, New York, 1943, p. 1.
16. R.R. Schrock, J.A. Osborn, J. Am. Chem. Soc. 93 (1971) 3089.
17. T. Ioannides, X. Veeykios, J. Catal. 140 (1993) 353.
18. K.J. Stanger, Y. Tang, J. Anderegg, R.J. Angelici, in preparation.
19. S. Hediger, B.H. Meier, R.R. Ernst, J. Chem. Phys. 102 (1995) 4000.
20. I. Ojima, T. Kogure, N. Yoda, J. Org. Chem. 45 (1980) 4728.
21. K. Achiwa, P.A. Chaloner, D. Parker, J. Organomet. Chem. 218 (1981) 249.
22. M.A. Garralda, L.A. Oro, Transition Met. Chem. 5 (1980) 63.
23. M. Green, T.A. Kuc, S.H. Taylor. J. Chem. Soc. A (1971) 2334.
24. - these signals disappear, Fig. 1f, indicating that any (PPM-Pd) complex is only weakly bound.
25. J. Halpern, D.P. Riley, A.S.C. Chan, J.J. Pluth, J. Am. Chem. Soc. 99 (1977) 8055.
26. A.S.C. Chan, J. Halpern, J. Am. Chem. Soc. 102 (1980) 838.
27. A.S.C. Chan, J.J. Pluth, J. Halpern, J. Am. Chem. Soc. 102 (1980) 5952.
28. (a) C.R. Landis, J. Halpern, J. Organomet. Chem. 250 (1983) 485;
29. (b) C.R. Landis, J. Halpern, J. Am. Chem. Soc. 109 (1987) 1746.
30. (a) I.D. Grdnev, N. Higashi, K. Asakura, T. Imamoto, J. Am. Chem. Soc. 122 (2000) 7194;
31. (b) I.D. Grdnev, N. Higashi, T. Imamoto, J. Am. Chem. Soc. 123 (2001) 4631.
32. (a) C.R. Landis, P. Hilfenhaus, S. Feldgus, J. Am. Chem. Soc. 121 (1999) 8741;
33. (b) S. Feldgus, C.R. Landis, J. Am. Chem. Soc. 122 (2000) 12714;
34. (c) S. Feldgus, C.R. Landis, Organometallics 20 (2001) 2374.
35. J.P. Collman, L.S. Hegedus, J.R. Norton, R.G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, CA, 1987.
36. R.R. Schrock, J.A. Osborn, J. Am. Chem. Soc. 93 (1971) 2397.
37. A.D. Zotto, L. Costella, A. Mezzetti, P. Rigo, J. Organomet. Chem. 414 (1991) 109.
38. L.M. Haines, Inorg. Chem. 10 (1971) 1693.
39. M.P. Keyes, K.L. Watters, J. Catal. 110 (1988) 96.
40. C.R. Guerra, J.H. Schulman, Surface Science 7 (1967) 229.
41. S.D. Worley, C.A. Rice, G.A. Mattson, C.W. Curtis, J.A. Guin, A.R. Tarrer, J. Phys. Chem. 86 (1982) 2714.
42. C.A. Rice, S.D. Worley, C.W. Curtis, A.J. Guin, A.R. Tarrer, J. Chem. Phys. 74 (1981) 6487.
43. K.S. Weddle, J.D. Aiken III, R.G. Finke, J. Am. Chem. Soc. 120 (1998) 5653.
44. G. Webb, J.I. Macnab, J. Catal. 26 (1972) 226.