Self-assembled Dendrimer-bound Pd(II) Complexes via Acid-base Interactions and their Catalysis for Allylic Amination

Chemistry Letters

Volumn 32, Issue 8, 2003, Pages 692-693

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

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; DENDRIMER; IMINE; MONOMER; PALLADIUM COMPLEX;

ACID BASE BALANCE; AMINATION; ARTICLE; CATALYSIS; CATALYST; COVALENT BOND; MOLECULAR INTERACTION;

EID: 0242636341     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.692     Document Type: Article

References (23)

1. For reviews and books on dendrimers, see: a) D. A. Tomalia, H. Baker, J. R. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder, and P. Smith, Polym. J., 17, 117 (1985). b) A. W. Bosman, H. M. Janssen, and E. W. Meijer, Chem. Rev., 99, 1665 (1999). c) "Dendrimers and Other Dendritic Polymers," ed. by J. M. J. Fréchet and D. A. Tomalia, J. Wiley & Sons, New York (2001). d) G. R. Newkome, C. N. Moorefield, and F. Vögtle, "Dendrimers and Dendrons: Concepts, Syntheses, Applications," Wiley-VCH, Weinheim (2001).
2. For reviews and books on dendrimers, see: a) D. A. Tomalia, H. Baker, J. R. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder, and P. Smith, Polym. J., 17, 117 (1985). b) A. W. Bosman, H. M. Janssen, and E. W. Meijer, Chem. Rev., 99, 1665 (1999). c) "Dendrimers and Other Dendritic Polymers," ed. by J. M. J. Fréchet and D. A. Tomalia, J. Wiley & Sons, New York (2001). d) G. R. Newkome, C. N. Moorefield, and F. Vögtle, "Dendrimers and Dendrons: Concepts, Syntheses, Applications," Wiley-VCH, Weinheim (2001).
3. For reviews and books on dendrimers, see: a) D. A. Tomalia, H. Baker, J. R. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder, and P. Smith, Polym. J., 17, 117 (1985). b) A. W. Bosman, H. M. Janssen, and E. W. Meijer, Chem. Rev., 99, 1665 (1999). c) "Dendrimers and Other Dendritic Polymers," ed. by J. M. J. Fréchet and D. A. Tomalia, J. Wiley & Sons, New York (2001). d) G. R. Newkome, C. N. Moorefield, and F. Vögtle, "Dendrimers and Dendrons: Concepts, Syntheses, Applications," Wiley-VCH, Weinheim (2001).
4. For reviews and books on dendrimers, see: a) D. A. Tomalia, H. Baker, J. R. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder, and P. Smith, Polym. J., 17, 117 (1985). b) A. W. Bosman, H. M. Janssen, and E. W. Meijer, Chem. Rev., 99, 1665 (1999). c) "Dendrimers and Other Dendritic Polymers," ed. by J. M. J. Fréchet and D. A. Tomalia, J. Wiley & Sons, New York (2001). d) G. R. Newkome, C. N. Moorefield, and F. Vögtle, "Dendrimers and Dendrons: Concepts, Syntheses, Applications," Wiley-VCH, Weinheim (2001).
5. For reviews on dendritic catalysts, see: a) G. E. Oosterom, J. N. H. Reek, P. C. J. Kamer, and P. W. N. M. van Leeuwen, Angew. Chem., Int. Ed., 40, 1828 (2001). b) D. Astruc and F. Chardac, Chem. Rev., 101, 2991 (2001). c) R. van Heerbeek, P. C. J. Kamer, P. W. N. M. van Leeuwen, and J. N. H. Reek, Chem. Rev., 102, 3717 (2002).
6. For reviews on dendritic catalysts, see: a) G. E. Oosterom, J. N. H. Reek, P. C. J. Kamer, and P. W. N. M. van Leeuwen, Angew. Chem., Int. Ed., 40, 1828 (2001). b) D. Astruc and F. Chardac, Chem. Rev., 101, 2991 (2001). c) R. van Heerbeek, P. C. J. Kamer, P. W. N. M. van Leeuwen, and J. N. H. Reek, Chem. Rev., 102, 3717 (2002).
7. For reviews on dendritic catalysts, see: a) G. E. Oosterom, J. N. H. Reek, P. C. J. Kamer, and P. W. N. M. van Leeuwen, Angew. Chem., Int. Ed., 40, 1828 (2001). b) D. Astruc and F. Chardac, Chem. Rev., 101, 2991 (2001). c) R. van Heerbeek, P. C. J. Kamer, P. W. N. M. van Leeuwen, and J. N. H. Reek, Chem. Rev., 102, 3717 (2002).
8. For recent reviews on polymer-bound metal complex catalysts, see: a) N. E. Leadbeater and M. Marco, Chem. Rev., 102, 3217 (2002). b) D. E. Bergbreiter, Chem. Rev., 102, 3345 (2002).
9. For recent reviews on polymer-bound metal complex catalysts, see: a) N. E. Leadbeater and M. Marco, Chem. Rev., 102, 3217 (2002). b) D. E. Bergbreiter, Chem. Rev., 102, 3345 (2002).
10. a) J. W. J. Knapen, A. W. van der Made, J. C. de Wilde, P. W. M. N. van Leeuwen, P. Wijkens, D. M. Grove, and G. van Koten, Nature, 372, 659 (1994).
11. b) M. T. Reetz, G. Lohmer, and R. Schwickardi, Angew. Chem., Int. Ed. Engl., 36, 1526 (1997).
12. D. de Groot, E. B. Eggeling, J. C. de Wilde, H. Kooijman, R. J. van Haaren, A. W. van der Made, A. L. Spek, D. Vogt, J. N. H. Reek, P. C. J. Kamer, and P. W. N. M. van Leeuwen, Chem. Commun., 1999, 1623.
13. N. J. Hovestad, E. B. Eggeling, H. J. Heidbuchel, J. T. B. H. Jastrzebski, U. Kragl, W. Keim, D. Vogt, and G. van Koten, Angew. Chem., Int. Ed., 38, 1655 (1999).
14. e) E. B. Eggeling, N. J. Hovestad, J. T. B. H. Jastrzebsky, D. Vogt, and G. van Koten, J. Org. Chem., 65, 8857 (2000).
15. T. Mizugaki, M. Ooe, K. Ebitani, and K. Kaneda, J. Mol. Catal. A: Chem., 145, 329 (1999).
16. T. Mizugaki, M. Murata, M. Ooe, K. Ebitani, and K. Kaneda, Chem. Commun., 2002, 52.
17. a) D. de Groot, B. F. M. de Waal, J. N. H. Reek, A. P. H. J. Schenning, P. C. J. Kamer, E. W. Meijer, and P. W. M. N. van Leeuwen, J. Am. Chem. Soc., 123, 8453 (2001).
18. b) R. van de Coevering, M. Kuil, R. J. M. K. Gebink, and G. van Koten, Chem. Commun., 2002, 1636.
19. M. Johannsen and K. A. Jorgensen, Chem. Rev., 98, 1689 (1998).
20. Recent report on heterogeneous Pd catalyst using polystyrene-based support functionalized with DPPBA, see: Y. Uozumi, H. Danjo, and T. Hayashi, Tetrahedron Lett., 38, 3557 (1997).
21. 4 as an external reference.
22. Typical procedures for the allylic amination of cinnamyl acetate with morpholine catalyzed by dendrimer-bound Pd complex 3a are as follows: to a catalyst solution prepared according to reference 10, was added cinnamyl acetate (3.0 mmol) and morpholine (4.5 mmol). After vigorous stirring of the reaction mixture at 5°C, the yields of products were determined by GC using an internal standard method.
23. B. M. Trost and E. Keinan, J. Am. Chem. Soc., 100, 7779 (1978).