Supramolecular Catalysts by Encapsulating Palladium Complexes within Dendrimers

Journal of the American Chemical Society

Volumn 126, Issue 6, 2004, Pages 1604-1605

  Ooe, Masahiko ^a   Murata, Makoto ^a   Mizugaki, Tomoo ^a   Ebitani, Kohki ^a   Kaneda, Kiyotomi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CARBONIC ACID; CINNAMIC ACID; CINNAMYL METHYL CARBONATE; DENDRIMER; IMINE; METHYL GROUP; MORPHOLINE; NANOPARTICLE; PALLADIUM COMPLEX; POLYPROPYLENE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; ENCAPSULATION; HECK REACTION; NANOREACTOR; PROTON NUCLEAR MAGNETIC RESONANCE; REACTOR; RECYCLING; SOLUBILITY; STEREOCHEMISTRY; SUPRAMOLECULAR CHEMISTRY;

EID: 1242336838     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038455m     Document Type: Article

References (24)

1. For books on dendrimers, see: (a) Fréchet, J. M. J., Tomalia, D. A., Eds. Dendrimers and Other Dendritic Polymers: J. Wiley & Sons: New York, 2001.
2. (b) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendrimers and Dendrons: Concepts, Syntheses, Applications; Wiley-VCH: Weinheim, 2001.
3. For recent reviews on dendritic catalysts, see: (a) Astruc, D.; Chardac, F. Chem. Rev. 2001, 101, 2991.
4. (b) van Heerbeek, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem. Rev. 2002, 102, 3717.
5. Jansen, J. F. G. A.; de Brabander-van den Berg, E. M. M.; Meijer, E. W. Science 1994, 266, 1226.
6. For several examples of dendrimer-encapsulated metal nanoparticle catalysts, see: (a) Ooe, M.; Murata, M.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Nano Lett. 2002, 2, 999.
7. (b) Scott, R. W. J.; Datye, A. K.; Crooks, R. M. J. Am. Chem. Soc. 2003, 125, 3708.
8. (a) de Groot, D.; de Waal, B. F. M.; Reek, J. N. H.; Schenning, A. P. H. J.; Kamer, P. C. J.; Meijer, E. W.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2001, 123, 8453.
9. (b) Ooe M.; Murata, M.; Takahama, A.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Chem. Lett. 2003, 32, 692.
10. Fan, Q.-H.; Chen, Y.-M.; Chen, X.-M.; Jiang, D.-Z.; Xi, F.; Chan, A. S. C. Chem. Commun. 2000, 789.
11. Boas, U.; Karlsson, A. J.; de Waal, B. F. M.; Meijer, E. W. J. Org. Chem. 2001, 66, 2136.
12. See Supporting Information for details.
13. For a recent reviews on Heck reaction, see: Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
14. For a recent example of the Heck reaction using dendrimer-encapsulated Pd nanoparticle catalysts, see: Yeung, L. K.; Lee, T., Jr.; Johnston, K. P.; Crooks, R. M. Chem. Commun. 2001, 2290.
15. For a recent review on allylic amination, see: Johannsen, M.; Jorgensen, K. A. Chem. Rev. 1998, 98, 1689.
16. The hydrogen bonds between the amide groups inside the dendrimer may weaken to increase the mobility of the surface groups of the dendrimer at a high temperature of 100 °C.
17. A similar phenomenon was observed using dendrimer-encapsulated Pd nanoparticles, see: Yeung, L. K.; Crooks, R. M. Nano Lett. 2001, 1, 14.
18. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry 2nd ed.; VCH: Weinheim, Germany, 1988; p 365.
19. For description of solvents affecting the regioselectivity in allylic substitution reactions with homogeneous Pd catalysts, see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545.
20. (b) Acemoglu, L.; Williams, J. M. J. Adv. Synth. Catal. 2001, 343, 75.
21. Oosterom, G. E.; Haaren, R. J.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Chem. Commun. 1999, 1119.
22. Mizugaki, T.; Ooe, M.; Ebitani, K.; Kaneda, K. J. Mol. Catal. A: Chem. 1999, 145, 329.
23. Eggeling, E. B.; Hovestad, N. J.; Jastrzebski, J. T. B. H.; Vogt, D.; van Koten, G. J. Org. Chem. 2000, 65, 8857.
24. Bergbreiter, D. E. Chem. Rev. 2002, 102, 3345.