"Click" dendrimer-stabilized palladium nanoparticles as a green catalyst down to parts per million for efficient C-C cross-coupling reactions and reduction of 4-nitrophenol

Advanced Synthesis and Catalysis

Volumn 356, Issue 11-12, 2014, Pages 2525-2538

  Deraedt, Christophe ^a   Salmon, Lionel ^b   Astruc, Didier ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

C C coupling; dendrimers; green chemistry; nanoreactors; palladium nanoparticles (PdNPs)

Indexed keywords

EID: 84906216706     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201400153     Document Type: Article

References (129)

1. Nanotechnology in Catalysis, Vols. 1 and 2, (Eds.,; B. Zhou, S. Hermans, G.A. Somorjai,), in: Nanostructure Science and Technology, Springer, Heidelberg, Berlin, 2003
2. Nanoparticles and Catalysis, (Ed.:, D. Astruc,) Wiley-VCH, Weinheim, 2008
3. Modern Surface Organometallic Chemistry, (Eds.:, J.-M. Basset, R. Psaro, D. Roberto, R. Ugo,), Wiley-VCH, Weinheim, 2009
4. L. M. Bronstein, Z. B. Shifrina, Chem. Rev. 2011, 111, 5301-5344
5. Nanomaterials in Catalysis, (Eds.:, P. Serp, K. Philippot,), Wiley-VCH, Weinheim, 2013.
6. M. T. Reetz, W. Helbig, S. A. Quaiser, in: Active metals: preparation, characterizations, applications, (Ed.:, A. Fürstner,), Wiley-VCH, Weinheim, 1996, p 279
7. I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066
8. J. G. deVries, Dalton Trans. 2006, 421-429.
9. M. Zhao, R. M. Crooks, Angew. Chem. 1999, 111, 375-377
10. Angew. Chem. Int. Ed. 1999, 38, 364-366
11. R. M. Crooks, M. Zhao, L. Sun, V. Chechik, L. K. Yeung, Acc. Chem. Res. 2001, 34, 181-190
12. R. W. J. Scott, H. C. Ye, R. R. Henriquez, R. M. Crooks, Chem. Mater. 2003, 15, 3873-3878
13. R. W. J. Scott, O. M. Wilson, R. M. Crooks, Phys. Chem. B 2005, 109, 692-704
14. V. S. Myers, M. W. Weier, E. V. Carino, D. F. Yancey, S. Pande, R. M. Crooks, Chem. Sci. 2011, 2, 1632-1646.
15. R. T. Reetz, E. Westermann, Angew. Chem. 2000, 112, 170-173
16. Angew. Chem. Int. Ed. 2000, 39, 165-168
17. H. Bönnemann, R. Richards, Eur. J. Inorg. Chem. 2001, 10, 2455-2480
18. Y. Li, M. A. El-Sayed, J. Phys. Chem. B 2001, 105, 8938-8943
19. A. H. M. deVries, J. M. C. A. Mulders, J. H. M. Mommers, H. J. W. Hendericks, J. G. deVries, Org. Lett. 2003, 5, 3285-3288
20. A. H. M. deVries, J. G. deVries, Eur. J. Org. Chem. 2003, 5, 799-811
21. M. T. Reetz, J. G. deVries, Chem. Commun. 2004, 14, 1559-1563
22. X. Tao, Y. Zhao, D. A. Sheng, Synlett 2004, 2, 359-361
23. D. Astruc, F. Lu, J. Ruiz, Angew. Chem. 2005, 117, 8062-8083
24. Angew. Chem. Int. Ed. 2005, 44, 7852-7872
25. D. Astruc, K. Heuze, S. Gatard, D. Méry, S. Nlate, L. Plault, Adv. Synth. Catal. 2005, 347, 329-338
26. N. T. S. Phan, M. vanderSluys, C. J. Jones, Adv. Synth. Catal. 2006, 348, 609-669
27. Metal-catalyzed Cross-coupling Reactions, (Eds.:, F. Diederich, P. Stang,), Wiley-VCH, Weinheim, 2008
28. R. P. Beletskaya, A. N. Kashin, I. A. Khotina, A. R. Khokhlov, Synlett 2008, 1547-1552
29. D. Astruc, Tetrahedron: Asymmetry 2010, 21, 1041-1054
30. B. Sreedhar, D. Yada, P. S. Reddy, Adv. Synth. Catal. 2011, 353, 2823-2836
31. P. Zhang, Z. Weng, J. Guo, C. Wang, Chem. Mater. 2011, 23, 5243-5249
32. M. Pagliaro, V. Pandarus, R. Ciriminna, F. Béland, P. DemmaCarà, ChemCatChem 2012, 4, 432-445
33. T. V. Magdesieva, O. M. Nikitina, O. A. Levitskya, V. A. Zinovyevab, I. Bezverkhyc, E. V. Zolotukhinab, M. A. Vorotyntsev, J. Mol. Catal. A 2012, 353-354, 50-57
34. Z. Guan, J. Hu, Y. Gu, H. Zhang, G. Li, T. Li, Green Chem. 2012, 14, 1964-1970.
35. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483
36. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359-1469
37. S. Kotha, K. Lahiri, D. Kashinath, Tetrahedron 2002, 58, 9633-9695
38. A. Suzuki, in: Modern Arene Chemistry, (Ed.:, D. Astruc,), Wiley-VCH: Weinheim, 2002, 53
39. F. Bellina, A. Carpita, R. Rossi, Synthesis 2004, 2419-2440.
40. 2O: 19/1, 90C in 95% yield and the Pd loading could be decreased to 25ppm. Under these conditions in toluene, bromobenzene gave a 50% yield using 0.05% Pd catalyst. The mechanism involved PdNP catalysts or precatalysts formed in situ at 90C., A. Alimardanov, L. Schmieder-vandeVondervoort, A. H. M. deVries, J. G. deVries, Adv. Synth. Catal. 2004, 346, 1812-1817
41. K. Okumara, T. Tomiyama, S. Okuda, H. Yoshida, M. Niwa, J. Catal. 2010, 273, 156-166
42. I. Favier, D. Madec, E. Teuma, M. Gõmez, Curr. Org. Chem. 2011, 15, 3127-3174
43. C. Zhou, J. Wang, L. Li, R. Wang, M. A. Hong, Green Chem. 2011, 13, 2100-2106
44. Y. M. A. Yamada, S. M. Sarkar, Y. Uozumi, J. Am. Chem. Soc. 2012, 134, 3190-3198.
45. P. D. Stevens, F. G. Li, J. D. Fan, M. Yen, Y. Gao, Chem. Commun. 2005, 4435-4437
46. R. Chinchilla, C. Najera, Chem. Rev. 2007, 107, 874-922
47. D. Astruc, Inorg. Chem. 2007, 46, 1884-1894
48. R. Chinchilla, C. Najera, Chem. Soc. Rev. 2011, 40, 5084-5121.
49. W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2-7
50. N. J. Whitcombe, K. K. Hii, S. E. Gibson, Tetrahedron 2001, 57, 7449-7476
51. V. Farina, Adv. Synth. Catal. 2004, 346, 1553-1582.
52. A. K. Diallo, C. Ornelas, L. Salmon, J. Ruiz, D. Astruc, Angew. Chem. 2007, 119, 8798-8802
53. Angew. Chem. Int. Ed. 2007, 46, 8644-8648
54. C. Ornelas, J. Ruiz, L. Salmon, D. Astruc, Adv. Synth. Catal. 2008, 350, 837-845
55. S. Ogasawara, S. Kato, J. Am. Chem. Soc. 2010, 132, 4608-4613
56. P. M. Uberman, L. M. Pérez, G. I. Lacconi, S. E. Martín, J. Mol. Catal. A: Chem. 2012, 363-364, 245-253
57. A. B. Patil, D. S. Patil, B. M. Bhanage, J. Mol. Catal. A: Chem. 2012, 365, 146-153
58. C. Deraedt, L. Salmon, L. Etienne, J. Ruiz, D. Astruc, Chem. Commun. 2013, 49, 8169-8171
59. C. Deraedt, L. Salmon, J. Ruiz, D. Astruc, Adv. Synth. Catal. 2013, 355, 2992-3001
60. C. Gao, H. Zhou, S. Wei, Y. Zhao, J. You, G. Gao, Chem. Commun. 2013, 49, 1127-1129.
61. P. Zhang, C. Shao, Z. Zhang, M. Zhang, J. Mu, Z. Guo, Y. Liu, Nanoscale 2011, 3, 3357-3363.
62. A. K. Diallo, E. Boisselier, L. Liang, J. Ruiz, D. Astruc, Chem. Eur. J. 2010, 16, 11832-11835.
63. V. Percec, C. Mitchell, W.-D. Cho, S. Uchida, M. Glodde, G. Ungar, X. Zeng, Y. Liu, V. S. K. Balagurusamy, J. Am. Chem. Soc. 2004, 126, 6078-6094.
64. E. Boisselier, A. K. Diallo, L. Salmon, C. Ornelas, J. Ruiz, D. Astruc, J. Am. Chem. Soc. 2010, 132, 2729-2742
65. D. Astruc, Nat. Chem. 2012, 4, 255-267
66. M. Bernechea, E. DeJesús, C. Lopez-Mardomingo, P. Terreros, Inorg. Chem. 2009, 48, 4491-4496
67. E. H. Rahim, F. S. Kamounah, J. Frederiksen, J. B. Christensen, Nano Lett. 2001, 1, 499-501
68. I. Nakamula, Y. Yamanoi, T. Imaoka, K. Yamamoto, H. Nishihara, Angew. Chem. 2011, 123, 5952-5955
69. Angew. Chem. Int. Ed. 2011, 50, 5830-5833
70. R. Djeda, A. Rapakousiou, L. Liang, N. Guidolin, J. Ruiz, D. Astruc, Angew. Chem. 2010, 122, 8328-8332
71. Angew. Chem. Int. Ed. 2010, 49, 8152-8156.
72. Ö. Metin, F. Durap, M. Aydemir, S. Özkar, J. Mol. Catal. A: Chem. 2011, 337, 39-44
73. D. Saha, K. Chattopadhyay, B. C. Ranu, Tetrahedron Lett. 2009, 50, 1003-1006
74. S. Sawoo, D. Srimani, P. Dutta, R. Lahiri, A. Sarkar, Tetrahedron 2009, 65, 4367-4374
75. L. Wang, C. Cai, J. Mol. Catal. A: Chem. 2009, 306, 97-101
76. L. Z. Ren, L. J. Meng, Express Polym. Lett. 2008, 2, 251-255
77. S. E. Lyubimov, A. A. Vasilev, A. A. Korlyukov, M. M. Ilyin, S. A. Pisarev, V. V. Matveev, A. E. Chalykh, S. G. Zlotin, V. A. Davankov, React. Funct. Polym. 2009, 69, 755-758
78. N. Jamwal, M. Gupta, S. Paul, Green Chem. 2008, 10, 999-1003
79. Z. Guan, J. Hu, Y. Gu, H. Zhang, H. Li, T. Li, Green Chem. 2012, 14, 1964-1970
80. G. Wei, W. Zhang, F. Wen, Y. Wang, M. Zhang, J. Phys. Chem. C 2008, 112, 10827-10832
81. V. Kogan, Z. Aizenshtat, R. Popovitz-Biro, R. Neumann, Org. Lett. 2002, 4, 3529-3532
82. X. Jiang, G. Wei, X. Zhang, W. Zhang, P. Zheng, F. Wen, L. Shi, J. Mol. Catal. A: Chem. 2007, 277, 102-106
83. A. Ohtaka, T. Teratani, R. Fujii, K. Ikeshita, T. Kawashima, K. Tatsumi, O. Shimomura, R. Nomura, J. Org. Chem. 2011, 76, 4052-4060
84. B. Karimi, D. Elhamifar, J. H. Clark, A. J. Hunt, Chem. Eur. J. 2010, 16, 8047-8053
85. C. M. Crudden, M. Sateesh, R. Lewis, J. Am. Chem. Soc. 2005, 127, 10045-10050
86. G. M. Scheuermann, L. Rumi, P. Steurer, W. Bannwarth, R. Mülhaupt, J. Am. Chem. Soc. 2009, 131, 8262-8270
87. A. Gniewek, J. Ziolkowski, A. Trzeciak, M. Zawadzki, H. Grabowska, J. Wrzyszcz, J. Catal. 2008, 254, 121-130
88. F. Churruca, R. SanMartin, B. Inés, I. Tellitu, E. Dominguez, Adv. Synth. Catal. 2006, 348, 1836-1840.
89. A. Khazaei, S. Rahmati, S. Saednia, Catal. Commun. 2013, 37, 9-13
90. P. Li, L. Wang, L. Zhang, G.-W. Wang, Adv. Synth. Catal. 2012, 354, 1307-1318
91. P. Veerakumar, M. Velayudham, K.-L. Lu, S. Rajagopal, Appl. Catal. A: General 2013, 455, 247-260
92. D. Ganapathy, G. Sekar, Catal. Commun. 2013, 39, 50-54
93. A. John, S. Modak, M. Madasu, M. Katari, P. Ghosh, Polyhedron 2013, 32, 20-29
94. S. Gao, N. Zhao, M. Shu, S. Che, Appl. Catal. A: General 2010, 388, 196-201
95. S. Moussa, A. R. Siamaki, B. F. Gupton, M. S. El-Shall, ACS Catal. 2012, 2, 145-154.
96. H. Li, L. Han, J. Cooper-White, I. Kim, Green Chem. 2012, 14, 586-591
97. K. Jiang, H. X. Zhang, Y. Y. Yang, R. Mothes, H. Lang, W. B. Cai, Chem. Commun. 2011, 47, 11924-11926
98. S. Harish, J. Mathiyarasu, K. L. N. Phani, V. Yegnaraman, Catal. Lett. 2009, 128, 197-202
99. Y. Mei, Y. Lu, F. Polzer, M. Ballauff, M. Drechsler, Chem. Mater. 2007, 19, 1062
100. X. Lu, X. Bian, G. Nie, C. Zhang, C. Wang, Y. Wei, J. Mater. Chem. 2012, 22, 12723-12730
101. J. Morere, M. J. Tenorio, M. J. Torralvo, C. Pando, J. A. R. Renuncio, A. Cabanas, J. Supercrit. Fluids 2011, 56, 213-222
102. R. Bhandari, M. R. Knecht, ACS Catal. 2011, 1, 89-98
103. B. Liu, S. Yun, Q. Wang, W. Hu, P. Jing, Y. Liu, W. Jia, Y. Liu, L. Liu, J. Zhang, Chem. Commun. 2013, 49, 3757-3759.
104. D. Jana, A. Dandapat, G. De, Langmuir 2010, 26, 12177-12184
105. J. Han, L. Li, R. Guo, Macromolecules 2010, 43, 10636-10644
106. C. Zhu, L. Han, P. Hu, S. Dong, Nanoscale 2012, 4, 1641-1646
107. Z. Zhang, C. Shao, P. Zou, P. Zhang, M. Zhang, M. Mu, Z. Guo, X. Li, C. Wang, Y. Liu, Chem. Commun. 2011, 47, 3906-3908
108. Y. Wang, G. Wei, W. Zhang, X. Jiang, P. Zheng, L. Shi, A. Dong, J. Mol. Catal. A: Chem. 2007, 266, 233-238
109. M. Zhang, L. Liu, C. Wu, G. Fu, H. Zhao, B. He, Polymer 2007, 48, 1989-1997
110. W. Liu, X. Yang, W. Huang, J. Colloid Interface Sci. 2006, 304, 160-165
111. Y. C. Chang, D. H. Chen, J. Hazard. Mater. 2009, 165, 664-669
112. H. Koga, E. Tokunaga, M. Hidaka, Y. Umemura, T. Saito, A. Isogai, T. Kitaoka, Chem. Commun. 2010, 46, 8567-8569
113. K. Kuroda, T. Ishida, M. Haruta, J. Mol. Catal. A: Chem. 2009, 298, 7-11
114. H. Yamamoto, H. Yano, H. Kouchi, Y. Obora, R. Arakawa, H. Kawasaki, Nanoscale 2012, 4, 4148-4154
115. S.-H. Wu, C.-T. Tseng, Y.-S. Lin, C.-H. Lin, Y. Hung, C.-Y. Mou, J. Mater. Chem. 2011, 21, 789-794
116. H. Wu, Z. Liu, X. Wang, B. Zhao, J. Zhang, C. Li, J. Colloid Interface Sci. 2006, 302, 142-148
117. H. Wu, X. Huang, M. Gao, X. Liao, B. Shi, Green Chem. 2011, 13, 651-658
118. K. B. Narayanan, N. Sakthivel, J. Hazard. Mater. 2011, 189, 519-525
119. W. Lu, R. Ning, X. Qin, Y. Zhang, G. Chang, S. Liu, Y. Luo, X. Sun, J. Hazard. Mater. 2011, 197, 320-326
120. X.-Y. Liu, F. Cheng, Y. Liu, H.-J. Liu, Y. Chen, J. Mater. Chem. 2010, 20, 360-368
121. J. Li, C.-Y. Liu, Y. Liu, J. Mater. Chem. 2012, 22, 8426-8430
122. H. Koga, T. Kitaoka, Chem. Eng. J. 2011, 168, 420-425
123. T. Huang, F. Meng, L. Qi, J. Phys. Chem. C 2009, 113, 13636-13642
124. R. Bhandari, M. R. Knecht, Catal. Sci. Technol. 2012, 2, 1360-1366
125. B. Ballarin, M. C. Cassani, D. Tonelli, E. Boanini, S. Albonetti, M. Blosi, M. Gazzano, J. Phys. Chem. C 2010, 114, 9693-9701
126. Y. Zhu, J. Shen, K. Zhou, C. Chen, X. Yang, C. Li, J. Phys. Chem. C 2011, 115, 1614-1619
127. Y. Xia, Z. Shi, Y. Lu, Polymer 2010, 51, 1328-1335
128. H. Wei, Y. Lu, Chem. Asian J. 2012, 7, 680-683
129. H. Yang, K. Nagai, T. Abe, H. Homma, T. Norimatsu, R. Ramaraj, ACS Appl. Mater. Inter. 2009, 1, 1860-1864.