Palladium nanoparticles in Suzuki cross-couplings: Tapping into the potential of tris-imidazolium salts for nanoparticle stabilization

Advanced Synthesis and Catalysis

Volumn 354, Issue 4, 2012, Pages 651-662

  Planellas, Marc ^a   Pleixats, Roser ^a   Shafir, Alexandr ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

imidazolium salts; nanoparticles; palladium; Suzuki Miyaura reaction

Indexed keywords

EID: 84858016909     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100574     Document Type: Article

References (75)

1. Nanoparticles. From Theory to Application, (Ed.:, G. Schmid,), 2 nd edn., Wiley-VCH, Weinheim, 2010.
2. Nanoparticles and Catalysis, (Ed.:, D. Astruc,), Wiley-VCH, Weinheim, 2008
3. A. Roucoux, J. Schulz, H. Patin, Chem. Rev. 2002, 102, 3757
4. M. Moreno-Mañas, R. Pleixats, Acc. Chem. Res. 2003, 36, 638
5. J. A. Widegren, R. G. Finke, J. Mol. Catal. A: Chem. 2003, 191, 187
6. D. Astruc, F. Lu, J. Ruiz Aranzaes, Angew. Chem. 2005, 117, 8062
7. Angew. Chem. Int. Ed. 2005, 44, 7852
8. J. G. De Vries, Dalton Trans. 2006, 421
9. D. Astruc, Inorg. Chem. 2007, 46, 1884
10. A. Roucoux, K. Philippot, in Handbook of Homogeneous Hydrogenations, (Eds.:, J. G. de Vries, C. J. Elsevier,), Wiley-VCH, Weinheim, 2007, vol. 9, pp 217- 255
11. A. Corma, H. García, Chem. Rev. 2008, 108, 2096
12. S. Roy, M. A. Pericàs, Org. Biomol. Chem. 2009, 7, 2669.
13. L. Starkey Ott, R. G. Finke, Coord. Chem. Rev. 2007, 251, 1075-1100.
14. P. Wasserscheid, W. Keim, Angew. Chem. 2000, 112, 3926-3945
15. Angew. Chem. Int. Ed. 2000, 39, 3772-3789
16. C. Chiappe, D. Pieraccini, J. Phys. Org. Chem. 2005, 18, 275-297
17. V. I. Pârvulescu, C. Hardacre, Chem. Rev. 2007, 107, 2615
18. H. Olivier-Bourbigou, L. Magna, D. Morvan, Appl. Catal. A: Gen. 2010, 373, 1-56
19. [2a], chapter 6, pp. 195-218.
20. J. Dupont, J. Spencer, Angew. Chem. 2004, 116, 5408-5409
21. Angew. Chem. Int. Ed. 2004, 43, 5296-5297
22. S. Chowdhury, R. S. Mohan, J. L. Scott, Tetrahedron 2007, 63, 2363-2389.
23. L. J. Xu, W. P. Chen, J. L. Xiao, Organometallics 2000, 19, 1123-1127
24. R. R. Deshmukh, R. Rajagopal, K. V. Srinivasan, Chem. Commun. 2001, 1544-1545
25. V. Calõ, A. Nacci, A. Moopoli, S. Laera, N. Cioffi, J. Org. Chem. 2003, 68, 2929-2933.
26. J. Dupont, J. D. Scholten, Chem. Soc. Rev. 2010, 39, 1780-1804.
27. P. Migowski, J. Dupont, Chem. Eur. J. 2007, 13, 32-39.
28. See the recent review article:, M. H. G. Prechtl, J. D. Scholten, J. Dupont, Molecules 2010, 15, 3441-3461, and references cited therein.
29. J. Huang, T. Jiang, B. Han, H. Gao, Y. Chang, G. Zhao, W. Wu, Chem. Commun. 2003, 1654-1655
30. P. Dash, S. M. Miller, R. W. J. Scott, J. Mol. Catal. A: Chem. 2010, 329, 86-95
31. P. Dash, R. W. J. Scott, Chem. Commun. 2009, 812-814
32. O. P. Khatri, K. Adachi, K. Murase, K. Okazaki, T. Torimoto, N. Tanaka, S. Kuwabata, H. Sugimura, Langmuir 2008, 24, 7785-7792
33. D. Raut, K. Wankhede, V. Vaidya, S. Bhilare, N. Darwatkar, A. Deorukhkar, G. Trivedi, M. Salunkhe, Catal. Commun. 2009, 10, 1240-1243
34. B. Léger, A. Denicourt-Nowicki, A. Roucoux, H. Olivier-Bourbigou, Adv. Synth. Catal. 2008, 350, 153-159
35. B. Léger, A. Denicourt-Nowicki, H. Olivier-Bourbigou, A. Roucoux, Tetrahedron Lett. 2009, 50, 6531-6533
36. X. Yang, Z. Fei, D. Zhao, W. Han Ang, Y. Li, P. J. Dyson, Inorg. Chem. 2008, 47, 3292-3297
37. Y. Hu, Y. Yu, Z. Hou, H. Li, X. Zhao, B. Feng, Adv. Synth. Catal. 2008, 350, 2077-2085
38. G. Salas, C. C. Santini, K. Philippot, V. Collière, B. Chaudret, B. Fenet, P. F. Fazzini, Dalton Trans. 2011, 40, 4660-4668
39. F. Fernández, B. Corder, J. Durand, G. Muller, F. Malbosc, Y. Kihn, E. Teuma, M. Gõmez, Dalton Trans. 2007, 5572-5581.
40. Y. Hu, H. Yang, Y. Zhang, Z. Hou, X. Wang, Y. Qiao, H. Li, B. Feng, Q. Huang, Catal. Commun. 2009, 10, 1903-1907
41. P. Singh, K. Kumari, A. Katyal, R. Kalra, R. Chandra, Catal. Lett. 2009, 127, 119-125
42. H. Zhang, H. Cui, Langmuir 2009, 25, 2604-2612
43. R. Venkatesan, M. H. G. Prechtl, J. D. Scholten, R. P. Pezzi, G. Machado, J. Dupont, J. Mater. Chem. 2011, 21, 3030-3036
44. Z. Wang, Q. Zhang, D. Juehner, A. Ivaska, L. Niu, Green Chem. 2008, 10, 907-909.
45. M. Trilla, R. Pleixats, T. Parella, C. Blanc, P. Dieudonné, Y. Guari, M. Wong Chi Man, Langmuir 2008, 24, 259-265.
46. M. Moreno-Mañas, R. Pleixats, S. Villarroya, Chem. Commun. 2002, 60-61. For Pd NPs with polyoxyethylenated stabilizers, see
47. A. Serra-Muns, R. Soler, E. Badetti, P. de Mendoza, M. Moreno-Mañas, R. Pleixats, R. M. Sebastián, A. Vallribera, New J. Chem. 2006, 30, 1584-1594.
48. A. Suzuki, J. Organomet. Chem. 1999, 576, 147
49. A. Suzuki, J. Organomet. Chem. 2002, 653, 83
50. A. Suzuki, Chem. Commun. 2005, 4759.
51. J.-P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651-2710
52. C. Torborg, M. Beller, Adv. Synth. Catal. 2009, 351, 3027-3043.
53. H.-K. Liu, W.-Y. Sun, H.-L. Zhu, K.-B. Yu, W.-X Tang, Inorg. Chim. Acta 1999, 295, 129-135.
54. K. Philippot, B. Chaudret, Organometallic Derived Metals, Colloids and Nanoparticles, in: Comprehensive Organometallic Chemistry III, (Eds.:, R. H. Crabtree, M. P. Mingos,), Elsevier 2007, vol. 12, ch. 12-03, pp 71- 99.
55. S. Jansat, J. Durand, I. Favier, F. Malbosc, C. Pradel, E. Teuma, M. Gõmez, ChemCatChem 2009, 1, 244-246
56. J. Durand, E. Teuma, F. Malbosc, Y. Kihn, M. Gõmez, Catal. Commun. 2008, 9, 273-275. For Pt NPs, see
57. C. W. Scheeren, G. Machado, J. Dupont, P. F. P. Fichtner, S. R. Teixeira, Inorg. Chem. 2003, 42, 4738-4742. For Ru NPs, see
58. E. T. Silveira, A. P. Umpierre, L. M. Rossi, G. Machado, J. Morais, G. V. Soares, I. L. R. Baumvol, S. R. Teixeira, P. F. P. Fichtner, J. Dupont, Chem. Eur. J. 2004, 10, 3734-3740
59. T. Gutel, J. García-Anton, K. Pelzer, K. Philippot, C. C. Santini, Y. Chauvin, B. Chaudret, J. M. Basset, J. Mater. Chem. 2007, 17, 3290-3292
60. T. Gutel, C. C. Santini, K. Philippot, A. Padua, K. Pelzer, B. Chaudret, Y. Chauvin, J. M. Basset, J. Mater. Chem. 2009, 19, 3624-3631. For Ni NPs, see
61. P. Migowski, G. Machado, S. R. Teixeira, M. C. M. Alves, J. Morais, A. Traverse, J. Dupont, Phys. Chem. Chem. Phys. 2007, 9, 4814-4821.
62. M. Tristany, B. Chaudret, P. Dieudonné, Y. Guari, P. Lecante, V. Matsura, M. Moreno-Mañas, K. Philippot, R. Pleixats, Adv. Funct. Mater. 2006, 16, 2008-2015.
63. M. Tristany, M. Moreno-Mañas, R. Pleixats, B. Chaudret, K. Philippot, P. Dieudonné, P. Lecante, J. Mater. Chem. 2008, 18, 660-666
64. M. Tristany, M. Moreno-Mañas, R. Pleixats, B. Chaudret, K. Philippot, Y. Guari, V. Matsura, P. Lecante, New J. Chem. 2009, 33, 1529-1534.
65. M. F. Rettig, P. M. Maitlis, Inorg. Synth. 1990, 28, 110-113.
66. K. Naka, M. Yaguchi, Y. Chujo, Chem. Mater. 1999, 11, 849-851
67. C. Pan, K. Pelzer, K. Philippot, B. Chaudret, F. Dassenoy, P. Lecante, M.-J. Casanove, J. Am. Chem. Soc. 2001, 123, 7584-7593.
68. P. Lara, O. Rivalda-Wheelaghan, S. Conejero, R. Poteau, K. Phillipot, B. Chaudret, Angew. Chem. 2011, 123, 1-7
69. Angew. Chem. Int. Ed. 2011, 50, 1-7. For other examples, see
70. J. Vignolle, T. D. Tilley, Chem. Commun. 2009, 7230-7232 (Au NP)
71. L. S. Ott, M. L. Cline, M. Deetlefs, K. R. Seddon, R. G. Finke, J. Am. Chem. Soc. 2005, 127, 5758-5759 (Ir NP)
72. J. D. Scholten, G. Ebeling, J. Dupont, Dalton Trans. 2007, 5554-5560 (Ir NP).
73. 1H NMR spectrum is also observed for 2b-Pd indicative of some interaction of the imidazolium moiety with the metal surface.
74. See, for example, C. C. Cassol, A. P. Umpierre, G. Machado, S. I. Wolke, J. Dupont, J. Am. Chem. Soc. 2005, 127, 3298-3299.
75. These conditions are known to lead to Pd-NHC species starting from imidazolium salts, for example, B. Karimi, D. Elhamifar, D J. H. Clark, A. J. Hunt, Chem. Eur. J. 2010, 16, 8047-8053.