Extremely efficient catalysis of carbon-carbon bond formation using "Click" dendrimer-stabilized palladium nanoparticles

Molecules

Volumn 15, Issue 7, 2010, Pages 4947-4960

  Astruc, Didier ^a   Ornelas, Cátia ^a   Diallo, Abdou K ^a   Ruiz, Jaime ^a  

^a INSTITUT DES SCIENCES MOLÉCULAIRES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DENDRIMER; NANOPARTICLE; PALLADIUM;

CATALYSIS; CHEMICAL REACTION; CHEMISTRY; REVIEW;

CATALYSIS; DENDRIMERS; NANOPARTICLES; ORGANIC CHEMISTRY PROCESSES; PALLADIUM;

EID: 77954988441     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15074947     Document Type: Review

References (100)

1. Kleij, R.A.; van Leeuwen, P.W.N.M.; van der Made, A.W. Catalyst compositions and polymerization process, hexakisphosphines and hexahalo compounds. EP0456317, 1991; [Chem. Abstr. 1992, 116, 129870].
2. Oosterom, G.E.; Reek, J.N.H.; Kamer, P.C.J.; van Leeuwen, P.W.N.M. Transition Metal Catalysis Using Functionalized Dendrimers. Angew. Chem. Int. Ed. 2001, 40, 1828-1849.
3. Brunner, H.; Fürst, J.; Ziegler, J. Enantioselektive katalyse: LXXXI. Optisch aktive zweischalenphosphine. J. Organomet. Chem. 1993, 454, 87-94.
4. Knapen, J.W.J.; van der Made, A.W.; de Wilde, J.C.; van Leeuwen, P.W.N.M.; Wijkens, P.; Grove, D.M.; van Koten, G. Homogeneous catalysts based on silane dendrimers functionalized with arylnickel(II) complexes. Nature 1994, 372, 659-663.
5. Miedaner, A.; Curtis, C.J.; Barkley, R.M.; DuBois, D.L. Electrochemical Reduction of CO2 Catalyzed by Small Organophosphine Dendrimers Containing Palladium. Inorg. Chem. 1994, 33, 5482-5490.
6. Lee, J.-J.; Ford, W.T.; Moore, J.A.; Li, Y. Reactivity of Organic Anions Promoted by a Quaternary Ammonium Ion Dendrimer. Macromolecules 1994, 27, 4632-4634.
7. Brunner, H. Dendrizymes: Expanded ligands for enantioselective catalysis. J. Organomet. Chem. 1995, 500, 39-46.
8. Ardoin, N.; Astruc, D. The Molecular Trees: From Syntheses towards Applications. Bull. Soc. Chim. Fr. 1995, 132, 875-909.
9. Astruc, D.; Chardac, F. Dendritic Catalysts and Dendrimers in Catalysis. Chem. Rev. 2001, 101, 2991-3031.
10. van Heerbeek, R.; Kamer, P.C.J.; van Leeuwen, P.W.N.M.; Reek, J.N.H. Dendrimers as Support for Recoverable Catalysts and Reagents. Chem. Rev. 2002, 102, 3717-3756.
11. Gade, L. Dendrimer Catalysis; Springer: Heidelberg, Germany, 2006.
12. Helms, B.; Fréchet, J.M.J. The Dendrimer Effect in Homogeneous Catalysis. Adv. Synth. Catal. 2006, 348, 1125-1148.
13. Méry, D; Astruc, D. Dendritic catalysis: Major concepts and recent progress. Coord. Chem. Rev. 2006, 250, 1965-1979.
14. Hwang, S.-H.; Shreiner, C.D.; Moorefield, C.N.; Newkome, C.N. Recent progress and applications for metallodendrimers. New J. Chem. 2007, 31, 1192-1217.
15. de Jesús, E.; Flores, J.C. Dendrimers: Solutions For Catalyst Separation and Recycling-A Review. Ind. Eng. Chem. Res. 2008, 47, 7968-7981.
16. Martinez-Olid, F.; Benito, J.M.; Flores, J.C.; de Jesus, E. Polymetallic Carbosilane Dendrimers Containing N,N'-Iminopyridine Chelating Ligands: Applications in Catalysis. Isr. J. Chem. 2009, 49, 99-108.
17. 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.
18. Tsuji, J. Modern Palladium Catalysis. Palladium Reagents and Catalysts: New Perspectives for the 21rst Century; Wiley: Chichester, UK, 2004.
19. Andrés, R.; de Jesus, E.; Flores, J.C. Catalysts based on palladium dendrimers. New J. Chem. 2007, 31, 1161-1191.
20. Astruc, D. Palladium Catalysis Using Dendrimers: Molecular Catalysts versus Nanoparticles. Tetrahedron Asymmetry 2010, in press.
21. Reetz, M.-T.; Lohmer, G.; Schwickardi, R. Systhesis and Catalytic Activity of Dendritic Diphosphane Metal Complexes. Angew. Chem. Int. Ed. Engl. 1997, 36, 1526-1529.
22. Dijskstra, H.P.; Kruihof, C.A.; Ronde, N.; van de Coevering, R.; Ramon, D.J.; Vogt, D.; van Klink, G.M.P.; van Koten, G. Shape-Persistent Nanosize Organometallic Complexes: Synthesis and Application in a Nanofiltration Membrane Reactor. J. Org. Chem. 2003, 68, 675-685.
23. Dijskstra, H.P.; Ronde, N.; Ramon, D.J.; van Klink, G.M.P.; Vogt, D.; van Koten, G. Application of a Homogeneous Dodecakis(NCN-PdII) Catalyst in a Nanofiltration Membrane Reactor under Continuous Reaction Conditions. Adv. Synth. Catal. 2003, 345, 364-369.
24. Astruc, D.; Heuze, K.; Gatard, S.; Méry, D.; Nlate, S.; Plault, L. Metallodendritic Catalysis for Redox and Carbon-Carbon Bond Formation Reactions: A Step towards Green Chemistry. Advan. Syn. Catal. 2005, 347, 329-338.
25. Brienbauer, R.; Jacobsen, E.N. Cooperative Asymmetric Catalysis with Dendrimeric [Co(salen)] Complexes. Angew. Chem. Int. Ed. 2000, 39, 3604-3607.
26. Francavilla, C.; Drake, M.D.; Bright, F.V.; Detty, M.R. Dendrimeric Organochalcogen Catalysts for the Activation of Hydrogen Peroxide: Improved Catalytic Activity through Statistical Effects and Cooperativity in Successive Generations. J. Am. Chem. Soc. 2001, 123, 57-67.
27. Dahan, A.; Portnoy, M. Dendritic effect in polymer-supported catalysis of the intramolecular Pauson-Khand reaction. Chem. Commun. 2002, 2700-2701.
28. Gatard, S.; Nlate, S.; Cloutet, E.; Bravic, G.; Blais, J.C.; Astruc, D. Dendritic Stars by Ring- Opening-Metathesis Polymerization from Ruthenium-Carbene Initiators. Angew. Chem. Int. Ed. 2003, 42, 452-456.
29. Dahan, A.; Portnoy, M. Remarkable Dendritic Effect in the Polymer-Supported Catalysis of the Heck Arylation of Olefins. Org. Lett. 2003, 5, 1197-2000.
30. Gatard, S.; Kahlal, S.; Méry, D.; Nlate, S.; Cloutet, E.; Saillard, J.-Y.; Astruc, D. Synthesis, Chemistry, DFT Calculations, and ROMP Activity of Monomeric Benzylidene Complexes Containing a Chelating Diphosphine and of Four Generations of Metallodendritic Analogues. Positive and Negative Dendritic Effects and Formation of Dendritic Ruthenium-Polynorbornene Stars. Organometallics 2004, 23, 1313-1324.
31. Fujihara, T.; Obora, Y.; Tokunaga, M.; Sato, H. Dendrimer N-heterocyclic carbene complexes with rhodium(I) at the core. Chem. Commun. 2005, 4526-4528.
32. Xang, X.; Xu, H.; Dong, Z.; Wang, Y.; Liu, J. Highly Efficient Dendrimer-Based Mimic of Glutathione Peroxidase. J. Am. Chem. Soc. 2004, 126, 10556-10557.
33. Delors, E.; Darbre, T.; Reymond, J.L. A Strong Positive Dendritic Effect in a Peptide Dendrimer- Catalyzed Ester Hydrolysis Reaction. J. Am. Chem. Soc. 2004, 126, 15642-15643.
34. Ouali, A.; Laurent, R.; Caminade, A.M.; Majoral, J.P.; Taillefer, M. Enhanced Catalytic Properties of Copper in O- and N-Arylation and Vinylation Reactions, Using Phosphorus Dendrimers as Ligands. J. Am. Chem. Soc. 2006, 128, 15990-15991.
35. Fujihara, T.; Yoshida, S.; Ohta, H.; Tsuji, Y. Triarylphosphanes with Dendritically Arranged Tetraethylene Glycol Moieties at the Periphery: An Efficient Ligand for the Palladium-Catalyzed Suzuki-Miyaura Coupling Reaction. Angew. Chem. Int. Ed. 2008, 47, 8310-8313.
36. Heuzé, K.; Méry, D.; Gauss, D.; Astruc, D. Copper-free, recoverable dendritic Pd catalysts for the Sonogashira reaction. Chem. Commun. 2003, 2274-2275.
37. Heuzé, K.; Méry, D.; Gauss, D.; Blais, J.-C.; Astruc, D. Copper-Free Monomeric and Dendritic Palladium Catalysts for the Sonogashira Reaction: Substituent Effects, Synthetic Applications, and the Recovery and Re-Use of the Catalysts. Chem. Eur. J. 2004, 10, 3936-3944.
38. Astruc, D.; Blais, J.-C.; Daniel, M.-C.; Gatard, S.; Nlate, S.; Ruiz, J. C. R. Nano-scale Metallodendritic Complexes in Electron-Transfer Processes and Catalysis. Chimie 2003, 6, 1117-1127.
39. Lemo, J.; Heuzé, K.; Astruc, D. Efficient Dendritic Diphosphino Pd(II) Catalysts for the Suzuki Reaction of Choroarenes. Org. Letters 2005, 7, 2253-2256.
40. Zhao, M.; Sun, L.; Crooks, R.M. Preparation of Cu Nanoclusters within Dendrimer Templates. J. Am. Chem. Soc. 1998, 120, 4877-4878.
41. Balogh, L.; Tomalia, D.A. Poly(Amidoamine) Dendrimer-Templated Nanocomposites. 1. Synthesis of Zerovalent Copper Nanoclusters. J. Am. Chem. Soc. 1998, 120, 7355-7356.
42. Esumi, K.; Suzuki, A.; Aihara, N.; Usu, K.; Torigoe, Preparation of Gold Colloids with UV Irradiation Using Dendrimers as Stabilizer K. Langmuir 1998, 14, 3157-3159.
43. Crooks, R.M.; Zhao, M.; Sun, L.; Chechik, V.; Yeung, L.K. Dendrimer-Encapsulated Metal Nanoparticles: Synthesis, Characterization, and Applications to Catalysis. Acc. Chem. Res. 2001, 34, 181-190.
44. Niu, Y.; Crooks, R.M. Dendrimer-encapsulated metal nanoparticles and their applications to catalysis C. R. Chimie 2003, 8, 1049-1059.
45. 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.
46. Zhao, M.; Crooks, R.M. Homogeneous Hydrogenation Catalysis with Monodisperse, Dendrimer- Encapsulated Pd and Pt Nanoparticles. Angew. Chem. Int. Ed. 1999, 38, 364-366.
47. Yeung, L.K.; Crooks, R.M. Heck Heterocoupling within a Dendritic Nanoreactor. Nano Lett. 2001, 1, 14-17.
48. Yeung, L.K.; Lee, C.T.; Johnston, K.P.; Crooks, R.M. Catalysis in supercritical CO2 using dendrimer-encapsulated palladium nanoparticles. Chem. Commun. 2001, 2290.
49. Scott, R.W.J.; Wilson, O.M.; Crooks, R.M. Titania-Supported Au and Pd Composites Synthesized from Dendrimer-Encapsulated Metal Nanoparticle Precursors. Chem. Mater. 2004, 16, 5682-5688.
50. Scottt, R.W.J.; Datye, A.K.; Crooks, R.M. Bimetallic Palladium-Platinum Dendrimer- Encapsulated Catalysts. J. Am. Chem. Soc. 2003, 125, 3708-3709.
51. Wilson, O.M.; Scott, R.W.J.; Garcia-Martinez, J.C.; Crooks, R.M. Synthesis, Characterization, and Structure-Selective Extraction of 1-3-nm Diameter AuAg Dendrimer-Encapsulated Bimetallic Nanoparticles. J. Am. Chem. Soc. 2005, 127, 1015-1024.
52. Scott, R.W.J.; Sivadiranarayana, C.; Wilson, O.M.; Yan, Z.; Goodman, D.W.; Crooks, R.M. Titania-Supported PdAu Bimetallic Catalysts Prepared from Dendrimer-Encapsulated Nanoparticle Precursors. J. Am. Chem. Soc. 2005, 127, 1380-1381.
53. Garcia-Martinez, J.C.; Lezutekong, R.; Crooks, R.M. Dendrimer- Encapsulated Pd Nanoparticles as Aqueous, Room-Temperature Catalysts for the Stille Reaction. J. Am. Chem. Soc. 2005, 127, 5097-5098.
54. Feng, Z.V.; Lyon, J.L.; Croley, J.S.; Crooks, R.M.; Vanden Bout, D.A.; Stevenson, K.J. Synthesis and Catalytic Evaluation of Dendrimer-Encapsulated Cu Nanoparticles. An Undergraduate Experiment Exploring Catalytic Nanomaterials. J. Chem. Ed. 2009, 86, 368-372.
55. Yamamoto, K.; Higushi, M.; Shiki, S.; Tsuruta, M.; Chiba, H. Stepwise radial complexation of imine groups in phenylazomethine dendrimers. Nature 2002, 415, 509-511.
56. Higushi, M.; Shiki, S.; Ariga, S.; Yamamoto, K. First Synthesis of Phenylazomethine Dendrimer Ligands and Structural Studies. J. Am. Chem. Soc. 2001, 123, 4414-4420.
57. Satoh, N.; Nakashima, T.; Kamikura, K.; Yamamoto, K. Quantum size effect in TiO2 nanoparticles prepared by finely controlled metal assembly on dendrimer templates. Nature Nanotechnol. 2008, 2, 106-111.
58. Nakamura, I.; Yamanoi, Y.; Yonezawa, T.; Imaoka, T.; Yamamoto, K.; Nishihara, H. Nanocage catalysts-rhodium nanoclusters encapsulated with dendrimers as accessible and stable catalysts for olefin and nitroarene hydrogenations. Chem. Commun. 2008, 5716-5718.
59. Beller, M.; Lohmer, G.; Kühlein, K.; Reisinger, C.P.; Herrmann, W.A. First palladium-catalyzed Heck reactions with efficient colloidal catalyst systems. J. Organomet. Chem. 1996, 520, 257.
60. Reetz, M.T.; Lohmer, G. Propylene carbonate stabilized nanostructured palladium clusters as catalysts in Heck reactions. Chem. Commun. 1996, 1921-1922.
61. Biffis, A.; Zecca, M.; Basato, M. Palladium metal catalysts in Heck C-C coupling reactions. J. Mol. Catal. A Chem. 2001, 173, 249-260.
62. Astruc, D.; Lu, F.; Ruiz, J. Nanoparticles as Recyclable Catalysts: The Fast-growing Frontier between Homogeneous and Heterogeneous Catalysts. Angew. Chem. Int. Ed. 2005, 44, 7852-7872.
63. Phan, N.T.S.; van der Sluis, M.; Jones, C.J. On the Nature of the Active Species in Palladium Catalyzed Mizoroki-Heck and Suzuki-Miyaura Couplings - Homogeneous or Heterogeneous Catalysis, A Critical Review. Adv. Syn. Catal. 2006, 348, 609-679.
64. de Vries, G.J. A unifying mechanism for all high-temperature Heck reactions. The role of palladium colloids and anionic species. Dalton. Trans. 2006, 421-429.
65. Astruc, D. Palladium Nanoparticles as Efficient Green Homogeneous and Heterogeneous Carbon- Carbon Coupling Pre-catalysts: A Unifying View. Inorg. Chem. 2007, 46, 1884-1894.
66. Djakovitch, L.; Köhler, K.; de Vries, J.G. The Role of Nanoparticles as Catalysts for Carbon- Carbon Coupling Reactions. In Nanoparticles and Catalysis; Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2007; Chapter 10, pp. 303-348.
67. He, J.-H.; Ichinose, I.; Kunitake, T.; Nakao, A.; Shiraishi, Y.; Toshima, N. Facile Fabrication of Ag-Pd Bimetallic Nanoparticles in Ultrathin TiO2-Gel Films: Nanoparticle Morphology and Catalytic Activity. J. Am. Chem. Soc. 2003, 125, 11034.
68. Newkome, G.R.; Moorefield, C.N.; Vögtle, F. Dendrimers and Dendrons. Concepts, Syntheses, Applications; Wiley-VCH: Weinheim, Germany, 2001.
69. Tomalia, D.A., Fréchet; J.M.J. Dendrimers and Other Dendritic Polymers; Wiley: Amsterdam, The Netherlands, 2001.
70. Astruc, D. Dendrimers and Nanosciences. C. R. Chimie 2003, 6, 709-1208.
71. Moulines, F.; Astruc, D. Tentacled Iron Sandwiches. Angew. Chem. Int. Ed. Engl. 1988, 27, 1347-1349.
72. + Induced Nona-Allylation of Mesitylene and Phase-Transfer Catalyzed Synthesis of a Redox Active Nona-Iron Complex. Angew. Chem. Int. Ed. Engl. 1993, 32, 1075-1077.
73. Sartor, V.; Djakovitch, L.; Fillaut, J.-L.; Moulines, F.; Neveu, F.; Marvaud, V; Guittard, J.; Blais, J.-C.; Astruc, D. Organoiron Routes to a New Dendron for Fast Dendritic Syntheses Using Divergent and Convergent Methods. J. Am. Chem. Soc. 1999, 121, 2929-2930.
74. Ruiz, J.; Lafuente, G.; Marcen, S.; Ornelas, C.; Lazare, S.; Cloutet, E.; Blais, J.-C.; Astruc, D. Construction of Giant Dendrimers Using a Tripodal Buiding Block. J. Am. Chem. Soc. 2003, 125, 7250-7257.
75. Astruc, D.; Ruiz, J. Organoiron-mediated dendrimer syntheses with 1→3 connectivity and applications. Tetrahedron Report N° 903. Tetrahedron 2010, 66, 1769-1785.
76. Astruc, D. Organo-iron complexes of aromatic compounds. Applications in synthesis. Tetrahedron Report N° 157. Tetrahedron 1983, 39, 4027-4095.
77. Catheline, D.; Astruc, D. The Use of Ferrocene in Organometallic Synthesis: A two Step Preparation of Cyclopentadienyliron Acetonitrile and Phosphine Cations via Photolysis of Cyclopentadienyliron Tricarbonyl or Arene Cations. J. Organometal. Chem. 1984, 272, 417-426.
78. Newkome, G.R.; Yao, Z.; Baker, G.R.; Gupta, V.K. Micelles. Part 1. Cascade molecules: A new approach to micelles. A [27]-arborol. J. Org. Chem. 1985, 50, 2003-2004.
79. Newkome, G.R.; Shreiner, C. The Syntheses of Dendrimers with 1→3 Connectivity. Chem. Rev. 2010, 110, in press.
80. Ornelas, C.; Méry, D.; Cloutet, E.; Ruiz, J.; Astruc, D. Cross Olefin Metathesis for the Selective Functionalization, Ferrocenylation, and Solubilization in Water of Olefin-terminated Dendrimers, Polymers and Gold Nanoparticles and for a Divergent Dendrimer Construction. J. Am. Chem. Soc. 2008, 130, 1495-1506.
81. Ornelas, C.; Ruiz, J.; Cloutet, E.; Alves, S.; Astruc, D. Click Assembly of 1,2,3-Triazole-Linked Dendrimers Including Ferrocenyl Dendrimers that Sense Both Oxo-anions and Metal Cations. Angew. Chem. Int. Ed. 2007, 46, 872-877.
82. Ornelas, C.; Salmon, L.; Ruiz, J.; Astruc, D. "Click" Dendrimers: Synthesis, Redox Sensing of Pd(OAc)2, and Remarkable Catalytic Hydrogenation Activity of Precise Pd Nanoparticles Stabilized by 1,2,3-Triazole-Containing Dendrimers. Chem. Eur. J. 2008, 14, 50-64.
83. Boisselier, E.; Diallo, A. K.; Salmon, L.; Ornelas, C.; Ruiz, J.; Astruc, D. Encapsulation and Stabilization of Gold Nanoparticles with "Click" Polyethyleneglycol Dendrimers. J. Am. Chem. Soc. 2010, 132, 2729-2742.
84. Daniel, M.-C.; Ruiz, J.; Blais, J.-C.; Daro, N.; Astruc, D. Synthesis of Five Generations of Redox Stable Pentamethylamidoferrocenyl Dendrimers and Compared Use of Amidoferrocenyl- and Pentamethylamidoferrocenyl Dendrimers As Electrochemical Exoreceptors for the Selective Recognition of H2PO4 -, HSO4 - and Adenosyl-5'-Triphosphate (ATP) Anions. Stereoelectronic and Hydrophobic Roles of the Cp Permethylation. Chem. Eur. J. 2003, 9, 4371-4379.
85. Astruc, D.; Ornelas, C.; Ruiz, J. Ferrocenyl-terminated Dendrimers: Design for Applications in Molecular Electronics, Molecular Recognition and Catalysis. J. Inorg. Organomet. Polym. Mater. 2008, 18, 4-17.
86. Astruc, D.; Ornelas, C.; Ruiz, J. Metallocenyl Dendrimers and their Applications in Molecular Electronics, Sensing and Catalysis. Acc. Chem. Res. 2008, 41, 841-856.
87. Badèche, S.; Daran, J.-C.; Ruiz, J.; Astruc, D. Synthesis and Coordination Chemistry of Ferrocenyl-1,2,3-triazolyl Ligands. Inorg. Chem. 2008, 47, 4903-4908.
88. Ornelas, C.; Salmon, L.; Ruiz, J.; Astruc, D. Catalytically Efficient Palladium Nanoparticles Stabilized by Click Ferrocenyl Dendrimers. Chem. Commun. 2007, 4946-4948.
89. Suzuki, A. The Susuki Reaction with Arylboron Compounds in Arene Chemistry. In Modern Arene Chemistry, Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002, pp. 53-106.
90. Diallo, A.K.; Ornelas, C.; Salmon, L.; Ruiz, J.; Astruc, D. Catalytically Efficient Palladium Nanoparticles Stabilized by Click Ferrocenyl Dendrimers. Angew. Chem. Int. Ed. Engl. 2007, 46, 8644-8648.
91. Ornelas, C.; Ruiz, J.; Salmon, L.; Astruc, D. Sulfonated "Click" Dendrimer-Stabilized Palladium Nanoparticles as Highly Efficient Catalysts for Olefin Hydrogenation and Suzuki Coupling Reactions Under Ambient Conditions in Aqueous Media. Adv. Syn. Catal. 2008, 350, 837-845.
92. Ornelas, C.; Diallo, A.K.; Ruiz, J.; Astruc, D. "Click" polymer-supported palladium nanoparticles as highly efficient catalysts for olefin hydrogenation and Suzuki coupling reaction under ambient conditions. Adv. Synth. Catal. 2009, 351, 2147-2154.
93. Lu, F.; Ruiz, J.; Astruc, D. Palladium-dodecanethiolate nanoparticles as stable and recyclable catalysts for the Suzuki-Miyaura reaction of aryl halides under ambient conditions. Tetrahedron Lett. 2004, 9443-9445.
94. Oee, M.; Murata, M.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Dendritic Nanoreactors Encapsulating Pd Particles for Substrate-Specific Hydrogenation of Olefins. Nano Lett. 2002, 2, 999.
95. Mizugaki, T.; Muratra, M.; Fukubayashi, S.; Mitsudome, T.; Jitsujkawa, K.; Kaneda, K. PAMAM dendron-stabilised palladium nanoparticles: Effect of generation and peripheral groups on particle size and hydrogenation activity. Chem. Commun. 2008, 241-243.
96. Lemo, J.; Heuzé, K.; Astruc, D. Synthesis and Catalytic Activity of DAB-dendrimer Encapsulated Pd Nanoparticles for the Suzuki Coupling Reaction. Inorg. Chim. Acta 2006, 359, 4909-4911.
97. Chung, Y.; Rhree, H.K. Partial hydrogenation of 1,3-cyclooctadiene using dendrimerencapsulated Pd-Rh bimetallic nanoparticles. J. Mol. Cat. A 2003, 206, 291-294
98. 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, 8572-8577.
99. 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, 499-502.
100. 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.