Sulphonated "click" dendrimer-stabilized palladium nanoparticles as highly efficient catalysts for olefin hydrogenation and Suzuki coupling reactions under ambient conditions in aqueous media

Advanced Synthesis and Catalysis

Volumn 350, Issue 6, 2008, Pages 837-845

  Ornelas, Cátia ^a   Ruiz, Jaime ^a   Salmon, Lionel ^b   Astruc, Didier ^a  

^a INSTITUT DES SCIENCES MOLÉCULAIRES   (France)

^b CNRS   (France)

Author keywords

Catalysis; Dendrimers; Nanoparticles; Palladium; Suzuki reaction

Indexed keywords

EID: 52949124507     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700584     Document Type: Article

References (65)

1. Aqueous-Phase Organometallic Catalysis. Concepts and Applications, 2nd edn., (Eds.: B. C. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 2004;
2. F. Joo, Acc. Chem. Res. 2002, 35, 738.
3. For aqueous-biphasically catalyzed Suzuki reactions using organometallic catalysts, see: M. Beller, J. G. E. Krauter, A. Zapf, Angew. Chem. Int. Ed. Engl. 1997, 36, 772;
4. E. Paetzold, G. Oehme, J. Mol. Cat. A 2000, 152, 69;
5. C. Dupuy, K. Adiey, L. Charruault, V. Michelet, M. Savignac, J.-P. Genêt, Tetrahedron Lett. 2001, 42, 6523.
6. P. T. Anastas, J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, New York, 1998.
7. H. Bönnemann, W. Brijoux, in: Active Metals, (Ed.: A. Fürstner), VCH, Weinheim, 1996, p 339;
8. M. T. Reetz, W. Helbig, S. A. Quaiser, in: Active Metals, (Ed.: A. Fürstner), VCH, Weinheim, 1996, p 279;
9. N. Toshima, Y. Yonezawa, New J. Chem. 1998, 22, 1179;
10. B. F. G. Johnson, Coord. Chem. Rev. 1999, 190, 1269;
11. A. Roucoux, J. Schulz, H. Patin, Chem. Rev. 2002, 102, 3757;
12. S. Mandal, P. R. Selvakannan, D. Roy, R. V. Chaudhari, M. Sastry, Chem. Commun. 2002, 3002;
13. J. Dupont, G. S. Fonseca, A. P. Umpierre, P. F. P. Fichner, J. Am. Chem. Soc. 2002, 124, 4228;
14. H. Ohde, C. M. Wai, J. Kim, M. Ohde, J. Am. Chem. Soc. 2002, 124, 4540;
15. A. Roucoux, J. Schulz, H. Patin, Adv. Syn. Catal. 2003, 345, 222;
16. H. Bönnemann, K. S. Nagabushana, in: Encyclopedia of Nanoscience and Nanotechnology, (Ed.: H. S. Nalwa), ASP, Stevenson Ranch, 2004, Vol. 1, p 777;
17. M. Bronstein, in: Encyclopedia of Nanoscience and Nanotechnology, Vol 7, (Ed.: H. S. Nalwa), ASP, Stevenson Ranch, 2004, p 193;
18. M. Bronstein, in: Dekker Encyclopedia of Nanoscience and Nanotechnology, (Eds.: J. A. Schwarz, C. I. Contescu, K. Putyera), Marcel Dekker, New York, 2004, p 2903;
19. F. Lu, J. R. Aranzaes, D. Astruc, Angew. Chem. Int. Ed. 2005, 44, 7852;
20. D. Astruc, Inorg. Chem. 2007, 46, 1884;
21. Nanoparticles and Catalysis, (Ed.: D. Astruc), Wiley-VCH, Weinheim, 2007.
22. For metallodendrimer catalysis, see: G. R. Newkome, E. He, C. N. Moorefield, Chem. Rev. 1999, 99, 1689;
23. D. Astruc, F. Chardac, Chem. Rev. 2001, 101, 2991;
24. G. E. Oosterom, J. N. H. Reek, P. C. J. Kamer, P. W. N. M. van Leeuwen, Angew. Chem. Int. Ed. 2001, 40, 1828;
25. R. Kreiter, A. W. Kleij, R. J. M. K. Gebbink, G. van Koten, in: Dendrimers IV: Metal Coordination, Self Assembly, Catalysis, (Eds.: F. Vögtle, C. A. Schalley), Top. Curr. Chem. Springer Verlag, Berlin, 2001, Vol. 217, p 163;
26. R. van Heerbeeck, P. C. J. Kamer, P. W. N. M. van Leeuwen, J. N. H. Reek, Chem. Rev. 2002, 102, 3717;
27. D. Astruc, D. Méry, Coord. Chem. Rev. 2005, 250, 1965.
28. M. Zhao, L. Sun, R. M. Crooks, J. Am. Chem. Soc. 1998, 120, 4877;
29. L. Balogh, D. A. Tomalia, J. Am. Chem. Soc. 1998, 120, 7355;
30. K. Esumi, A. Suzuki, N. Aihara, K. Usui, K. Torigoe, Langmuir 1998, 14, 3157.
31. Reviews: R. M. Crooks, M. Zhao, L. Sun, V. Chechik, L. K. Yeung, Acc. Chem. Res. 2001, 34, 181;
32. R. W. J. Scott, O. M. Wilson, R. M. J. Crooks, Phys. Chem. B 2005, 109, 692.
33. For click chemistry, see: H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. 2001, 40, 2004;
34. V. D. Bock, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2006, 51.
35. a) C. Ornelas, J. R. Aranzaes, E. Cloutet, S. Alves, D. Astruc, Angew. Chem. Int. Ed. Engl. 2007, 46, 872;
36. b) C. Ornelas, L. Salmon, J. Ruiz, D. Astruc, Chem. Commun. 2007, 4946;
37. c) A. Diallo, C. Ornelas, J. R. Aranzaes, L. Salmon, D. Astruc, Angew. Chem. Int. Ed. 2007, 46, 8644;
38. C. Ornelas, L. Salmon, J. Ruiz, D. Astruc, Chem. Eur. J. 2008, 14, 50.
39. A. H. M. de Vries, F. J. Parlevliet, L. Schmeder-van de Vondervoort, J. H. M. Mommers, H. J. W. Henderickx, M. A. N. Walet, J. G. de Vries, Adv. Synth. Catal. 2002, 344, 996;
40. A. H. M. de Vries, J. M. C. A. Mulders, J. H. M. Mommers, H. J. W. Hendericks, J. G. de Vries, Org. Lett. 2003, 5, 3285;
41. J. G. de Vries, Dalton Trans. 2006, 421;
42. N. T. S. Phan, M. Van der Sluys, C. J. Jones, Adv. Synth. Catal. 2006, 348, 609.
43. a) F. Moulines, D. Astruc, Angew. Chem. Int. Ed. Engl. 1988, 27, 1347;
44. F. Moulines, L. Djakovitch, R. Boese, B. Gloaguen, W. Thiel, J.-L. Fillaut, M.-H. Delville, D. Astruc, Angew. Chem. Int. Ed. Engl. 1993, 32, 1075;
45. V. Sartor.; L. Djakovitch, J.-L. Fillaut, F. Moulines, F. Neveu, V. Marvaud, J. Guittard, J.-C. Blais, D. Astruc, J. Am. Chem. Soc. 1999, 121, 2929;
46. b) J. Ruiz, G. Lafuente, S. Marcen, C. Ornelas, S. Lazare, J.-C. Blais, E. Cloutet, D. Astruc, J. Am. Chem. Soc. 2003, 125, 7250.
47. 3): D. V. Leff, P. C. Ohara, J. R. Heath, W. M. Gelbart, J. Phys. Chem. 1995, 99, 7036;
48. A. Labande, J. Ruiz, J. , D. Astruc, J. Am. Chem. Soc. 2002, 124, 1782;
49. M.-C. Daniel, J. Ruiz, S. Nlate, J.-C. Blais, D. Astruc J. Am. Chem. Soc. 2003, 125, 2617;
50. R. W. J. Scott, O. M. Wilson, S.-K. Oh, E. A. Kenik, R. M. Crooks, J. Am. Chem. Soc. 2004, 126, 15583.
51. Y. Niu, L. K. Yeung, R. M. Crooks, J. Am. Chem. Soc. 2001, 123, 6840;
52. S.-K. Oh, Y. Niu, R. M. Crooks, Langmuir 2005, 21, 10209;
53. O. M. Wilson, M. R. Knecht, J. C. Garcia-Martinez, R. M. Crooks, J. Am. Chem. Soc. 2006, 128, 4510.
54. E. H. Rahim, F. S. Kamounah, J. Frederiksen, J. B. Christensen, Nano Letters 2001, 9, 499;
55. L. K. Yeung, R. M. Crooks, Nano Letters 2001, 1, 14;
56. M. Pittelkow, K. Moth-Poulsen, U Boas, J. B. Christensen, Langmuir 2003, 19, 7682;
57. R. Narayanan, M. A. El-Sayed, J. Phys. Chem. B 2004, 108, 8572.
58. E.-H. Ryu, Y. Zhao, Org. Lett. 2005, 6, 1035.
59. K. Heuze, D. Mery, D. Gauss, D. Astruc Chem. Commun. 2003, 2274;
60. K. Heuzé, D. Méry, D. Gauss, J.-C. Blais, D. Astruc, Chem. Eur. J. 2004, 10, 3936;
61. J. Lemo, K. Heuzé, D. Astruc Org. Lett. 2005, 7, 2253;
62. Y. F. Lu, J. Ruiz, D. Astruc Tetrahedron Lett. 2004, 9443;
63. D. Astruc, K. Heuze, S. Gatard, D. Méry, S. Nlate, L. Plault Adv. Synth. Catal. 2005, 347, 329;
64. J. Lemo, K. Heuze, D. Astruc Inorg. Chim. Acta 2006, 359, 4909;
65. J. Lemo, K. Heuze, D. Astruc Chem. Commun. 2007, 4351.