Palladium(0) deposited on PAMAM dendrimers as a catalyst for C-C cross coupling reactions

Molecules

Volumn 16, Issue 1, 2011, Pages 427-441

  Borkowski, Tomasz ^a   Subik, Paweł ^b   Trzeciak, Anna M ^a   Wołowiec, Stanisław ^b  

^a UNIVERSITY OF WROC AW   (Poland)

^b RZESZOW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Dendrimers; Heck coupling; Hiyama coupling; Palladium nanoparticles; Sonogashira coupling; Suzuki miyaura coupling; TEM

Indexed keywords

ACETYLENE; BIPHENYLACETYLENE; DENDRIMER; DRUG DERIVATIVE; PALLADIUM; PAMAM STARBURST;

ARTICLE; CATALYSIS; CHEMISTRY; TRANSMISSION ELECTRON MICROSCOPY;

ACETYLENE; CATALYSIS; DENDRIMERS; MICROSCOPY, ELECTRON, TRANSMISSION; PALLADIUM;

EID: 79251484692     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16010427     Document Type: Article

References (38)

1. Astruc, D.; Boisselier, E.; Ornelas, C. Dendrimers Designed for Functions: From Physical, Photophysical, and Supramolecular Properties to Applications in Sensing, Catalysis, Molecular Electronics, Photonics, and Nanomedicine. Chem. Rev. 2010, 110, 1857-1959.
2. Astruc, D.; Lu, F.; Aranzaes, J. R. Nanoparticles as recyclable catalysts: the frontier between homogeneous and heterogeneous catalysis. Angew. Chem. Int. Ed. 2005, 44, 7852-7872.
3. Scott, R. W. J.; Wilson, O. M.; Crooks, R. M. Synthesis, characterization and applications of dendrimer-encapsulated nanoparticles. J. Phys. Chem. B 2005, 109, 692-704.
4. Crooks, R. M.; Zhao, M.; Sun, L.; Chechik, V.; Yeung, L. K. Dendrimer-encapsulated metal nanoparticles: synthesis, characterization and application to catalysis. Acc. Chem. Res. 2001, 34, 181-190.
5. Andrés, R.; de Jesús, E.; Flores, J. C. Catalysts based on palladium dendrimers. New J. Chem. 2007, 31, 1161-1191.
6. Tomalia, D. A. Birth of a new macromolecular architecture: dendrimers as quantized building blocks for nanoscale synthetic polymer chemistry. Progr. Polym. Sci. 2005, 30, 294-324.
7. Garcia-Martinez, J. C.; Scott, R. W. J.; Crooks, R. M. Extraction of monodisperse palladium nanoparticles from dendrimer template. J. Am. Chem. Soc. 2003, 125, 11190-11191.
8. Astruc, D.; Ornelas, C.; Ruiz, J. Metallocenyl dendrimers and their applications in molecular electronics, sensing and catalysis. J. Acc. Chem. Res. 2008, 41, 841.
9. Tomalia, D. A.; Naylor, A. M.; Goddard, W. A. Starburst dendrimers: molecular - level control of size, shape, surface chemistry, topology and flexibility from atoms to macroscopic matter. Angew. Chem. Int. Ed. Engl. 1990, 29, 138-175.
10. Moreno-Manas, M.; Pleixats, R. Formation of carbon-carbon bonds under catalysis by transitionmetal nanoparticles. Acc. Chem. Res. 2003, 36, 638-648.
11. Durand, J.; Teuma, E.; Gomez, M. An overview of palladium nanocatalysts: surface and molecular reactivity. Eur. J. Inorg. Chem. 2008, 3577-3586.
12. Esami, K.; Isono, R.; Yoshimura, T. Preparation of PAMAM-and PPI-Metal (Silver, Platinum, and Palladium) Nanocomposites and Their Catalytic Activities for Reduction of 4-Nitrophenol. Langmuir 2004, 20, 237-243.
13. Touzani, R.; Alper, H. PAMAM dendrimer-palladium complex catalyzed synthesis of five-, sixor seven membered ring lactones and lactams by cyclocarbonylation methodology. J. Mol. Catal. A 2005, 227, 197-207.
14. Gomez, M. V.; Guerra, J.; Velders, A. H.; Crooks, R. M. NMR Characterization of Fourth-Generation PAMAM Dendrimers in the Presence and Absence of Palladium Dendrimer-Encapsulated Nanoparticles. J. Am. Chem. Soc. 2009, 131, 341-350.
15. Tsuji, Y.; Fujihara, T. Homogeneous Nanosize Palladium Catalysts. Inorg. Chem. 2007, 46, 1895-2002.
16. Rahim, E. H.; Kamounah, F. S.; Frederiksen, J.; Christensen, J. B. Heck reactions catalyzed by PAMAM-dendrimer encapsulated Pd (0) nanoparticles. Nano Lett. 2001, 1, 499-501.
17. Kühnert, J.; Lamač, M.; Demel, J.; Nicolai, A.; Lang, H.; Štěpnička, P. Phosphinoferrocenylterminated amidoamines: synthesis and catalytic utilization in palladium-mediated C-C bond forming reactions. J. Mol. Catal. A: Chem. 2008, 285, 41-47.
18. Ooe, M.; Murata, M.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Supramolecular Catalysts by Encapsulating Palladium Complexes within Dendrimers. J. Am. Chem. Soc. 2004, 126, 1604-1605.
19. II-phosphine complexes modified poly (ether imine) dendrimers. Tetrahedron 2004, 60, 10325-10334.
20. Heuzé, K.; Méry, D.; Gauss, D.; Astruc, D. Copper-free, recoverable dendritic Pd catalysts for the Sonogashira reaction. Chem. Commun. 2003, 2274-2275.
21. Smith, G.; Chen, R.; Mapolie, S. The synthesis and catalytic activity of a first-generation poly (propylene imine) pyridylimine palladium metallodendrimer. J. Organomet. Chem. 2003, 673, 111-115.
22. Smith, G.; Mapolie, S. Iminopyridyl-palladium dendritic catalyst precursors: evaluation in Heck reactions. J. Mol. Catal. A. 2004, 213, 187-192.
23. Karakhanov, E.; Maximov, A. L.; Tarasevich, B.; Skorki, V. A. Dendrimer-based catalysts in Wacker-oxidation: Unexpected selectivity to terminal double bonds. J. Mol. Catal. A. 2009, 297, 73-79.
24. Bernechea, M.; de Jesus, E.; Lopez-Mardomingo, C; Terreros, P. Dendrimer-encapsulated Pd nanoparticles versus palladium acetate as catalytic precursors in the Stille reaction in water. Inorg. Chem. 2009, 48, 4491-4496.
25. Ogasawara, S.; Kato, S. Palladium nanoparticles captured in microporous polymers: a tailor-made catalyst for heterogeneous carbon cross-coupling reactions. J. Am. Chem. Soc. 2010, 132, 4608-4613.
26. Zheng, Z.; Li, H.; Liu, T.; Cao, R. Monodisperse noble metal nanoparticle stabilized in SBA-15: synthesis, characterization and application in microwave-assisted Suzuki-Miyaura coupling reaction. J. Catal. 2010, 270, 268-274.
27. Narayanan, R.; El-Sayed, M. A. Effect of colloidal catalysis on the nanoparticle size distribution: dendrimer-Pd vs PVP-Pd nanoparticles catalyzing the Suzuki coupling reaction. J. Phys. Chem. B 2004, 108, 8572-8580.
28. Narayanan, R.; El-Sayed, M. Some aspects of colloidal nanoparticle stability, catalytic activity, and recycling potential. Top. Catal. 2008, 47, 15-21.
29. Gniewek, A.; Trzeciak, A. M.; Ziólkowski, J. J.; Kȩpiński, L.; Wrzyszcz, J.; Tylus, W. Pd-PVP colloid as catalyst for Heck and carbonylation reactions; TEM and XPS studies. J. Catal. 2005, 229, 332-343.
30. Gniewek, A; Ziólkowski, J. J.; Trzeciak, A. M.; Zawadzki, M.; Grabowska, H.; Wrzyszcz J. Palladium nanoparticles supported on alumina-based oxides as heterogeneous catalysts of the Suzuki-Miyaura reaction. J. Catal. 2008, 254, 121-130.
31. Subik, P.; Białońska, A.; Wołowiec, S. Tetraazacyclotetradecane isomeric macrocycles with Schiff base loops and dimanganese (II) complex of one of the isomers. Polyhedron 2011, In Press.
32. Pittelkow, M.; Moth-Poulsen, K.; Boas, U.; Christensen, J. B. Poly (amidoamine)-dendrimerstabilized Pd (0) nanoparticles as a catalyst for the Suzuki reaction. Langmuir 2003, 19, 7682-7684.
33. Pryjomska-Ray, I.; Gniewek, A.; Trzeciak, A. M.; Ziół kowski, J. J.; Tylus, W. Homogeneous/heterogeneous palladium based catalytic system for Heck reaction. The reversible transfer of palladium between solution and support. Topic. Catal. 2006, 173-184.
34. Pryjomska-Ray, I.; Trzeciak, A. M.; Ziółkowski, J. J. Base-free, efficient palladium catalyst of Heck reaction in molten tetrabutylammonium bromide. J. Mol. Catal. A: Chem. 2006, 257, 3-8.
35. Tomalia, D. A.; Huang, B.; Swanson, D. R; Brothers, H. M.; Klimash, J. W. Structure control within poly (amidoamine) dendrimers: size, shape and regio-chemical mimicry of globular proteins. Tetrahedron 2003, 59, 3799-3813.
36. Subik, P.; Welc, B.; Wisz, B.; Wołowiec, S. Stable hemiaminals attached to PAMAM dendrimers. Tetrahedron Lett. 2009, 50, 6512-6514.
37. Calo, V.; Nacci, A.; Monopoli, A.; Fornaro, A.; Sabbatini, L.; Cioffi, N.; Ditaranto, N. Heck reaction catalyzed by nanosized palladium on chitosan in ionic liquid. Organometllics 2004, 23, 5154-5158.
38. Calo, V.; Nacci, A.; Monopoli, A.; Laera, S.; Cioffi, N. J. Pd nanoparticles catalyzed stereospecific synthesis of β-aryl cinnamic esters in ionic liquids. Org. Chem. 2003, 68, 2929-2933.