Palladium nanoparticles immobilized on nano-silica triazine dendritic polymer (Pdnp-nSTDP): An efficient and reusable catalyst for suzuki-miyaura cross-coupling and heck reactions

Advanced Synthesis and Catalysis

Volumn 355, Issue 5, 2013, Pages 957-972

  Isfahani, Amir Landarani ^a   Mohammadpoor Baltork, Iraj ^a   Mirkhani, Valiollah ^a   Khosropour, Ahmad R ^a   Moghadam, Majid ^a   Tangestaninejad, Shahram ^a   Kia, Reza ^b  

^a UNIVERSITY OF ISFAHAN   (Iran)

^b ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Heck reaction; palladium nanoparticles; reusable catalyst; Suzuki Miyaura cross coupling; triazine dendritic polymer

Indexed keywords

EID: 84875446411     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201200707     Document Type: Article

References (82)

1. A. Balanta, C. Godard, C. Claver, Chem. Soc. Rev. 2011, 40, 4973-4985.
2. C. Burda, X. Chen, R. Narayanan, M. A. El-Sayed, Chem. Rev. 2005, 105, 1025-1102.
3. D. Astruc, Tetrahedron: Asymmetry 2010, 21, 1041-1054
4. L. S. Ott, R. G. Finke, Coord. Chem. Rev. 2007, 251, 1075-1100.
5. L. Yin, J. Liebscher, Chem. Rev. 2007, 107, 133-173
6. S. Shylesh, V. Schünemann, W. R. Thiel, Angew. Chem. 2010, 122, 3504-3537
7. Angew. Chem. Int. Ed. 2010, 49, 3428-3459
8. M. Lamblin, L. Nassar-Hardy, J.-C. Hierso, E. Fouquet, F.-X. Felpin, Adv. Synth. Catal. 2010, 352, 33-79.
9. F. Vögtle, G. Richardt, N. Werner, Dendrimer Chemistry, Wiley-VCH, Weinheim, 2009
10. D. Astruc, E. Boisselier, C. Ornelas, Chem. Rev. 2010, 110, 1857-1959.
11. G. R. Newkome, C. N. Moorefield, Chem. Rev. 1999, 99, 1689-1746
12. A. W. Bosman, E. W. Jensen, E. W. Meijer, Chem. Rev. 1999, 99, 1665-1688
13. M. W. P. L. Baars, R. Klepingler, M. H. J. Koch, S. L. Yeu, E. W. Meijer, Angew. Chem. 2000, 112, 1341-1344
14. Angew. Chem. Int. Ed. 2000, 39, 1341-1344.
15. K. Vassilev, S. Turmanova, M. Dimitrova, S. Boneva, Eur. Polym. J. 2009, 45, 2269-2278
16. A. Berger, R. J. M. K. Gebbink, G. van Koten, Top. Organomet. Chem. 2006, 20, 1-38
17. C. Ornelas, J. R. Aranzaes, L. Salmon, D. Astruc, Chem. Eur. J. 2008, 14, 50-64
18. C. Hajji, R. Haag, Top. Organomet. Chem. 2006, 20, 149-176
19. L. Wu, Z.-W. Li, F. Zhang, Y.-M. He, Q.-H. Fan, Adv. Synth. Catal. 2008, 350, 846-862
20. C. Ornelas, J. Ruiz, L. Salmon, D. Astruc, Adv. Synth. Catal. 2008, 350, 837-845.
21. S. Antebi, P. Arya, L. E. Manzer, H. Alper, J. Org. Chem. 2002, 67, 6623-6631
22. P. P. Zweni, H. Alper, Adv. Synth. Catal. 2004, 346, 849-854
23. R. Touzani, H. Alper, J. Mol. Catal. A: Chem. 2005, 227, 197-207
24. J. P. K. Reynhardt, Y. Yang, A. Sayari, H. Alper, Adv. Synth. Catal. 2005, 347, 1379-1388
25. P. P. Zweni, H. Alper, Adv. Synth. Catal. 2006, 348, 725-731
26. W. Huang, J. N. Kuhn, C.-K. Tsung, Y. Zhang, S. E. Habas, P. Yang, G. A. Somorjai, Nano Lett. 2008, 8, 2027-2034
27. G. Jayamurugan, C. P. Umesh, N. Jayaraman, J. Mol. Catal. A: Chem. 2009, 307, 142-148
28. H. Hagiwara, H. Sasaki, N. Tsubokawa, T. Hoshi, T. Suzuki, T. Tsuda, S. Kuwabata, Synlett 2010, 1990-1996.
29. M. B. Steffensen, E. E. Simanek, Org. Lett. 2003, 5, 2359-2361
30. S. Yoo, J. D. Lunn, S. Gonzalez, J. A. Ristich, E. E. Simanek, D. F. Shantz, Chem. Mater. 2006, 18, 2935-2942
31. S. J. Dilly, S. J. Carlisle, A. J. Clark, A. R. Sheperd, S C. Smith, P. C. Taylor, A. Marsh, J. Polym. Sci. Part A: Polym. Chem. 2006, 44, 2248-2259
32. E. E. Simanek, H. Abdou, S. Lalwani, J. Lim, M. Mintzer, V. J. Venditto, B. Vittur, Proc. R. Soc. London Ser. A 2010, 466, 1445-1468.
33. M. P. Kapoor, H. Kuroda, M. Yanagi, H. Nanbu, L. R. Juneja, Top. Catal. 2009, 52, 634-642.
34. R. Ghanbaripour, I. Mohammadpoor-Baltork, M. Moghadam, A. R. Khosropour, S. Tangestaninejad, V. Mirkhani, Polyhedron 2012, 31, 721-728
35. S. Safaei, I. Mohammadpoor-Baltork, A. R. Khosropour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, Adv. Synth. Catal. 2012, 354, 3095-3104.
36. N. Tsubokawa, H. Ichioka, T. Satoh, S. Hayashi, K. Fujiki, React. Funct. Polym. 1998, 31, 75-82.
37. R. M. Silverstein, G. C. Bassler, T. C. Morril, Spectrometric Identification of Organic Compounds, 6 th edn., Wiley, New York, 1998.
38. R. Bernini, S. Cacchi, G. Fabrizi, G. Forte, F. Petrucci, A. Prastaro, S. Niembro, A. Shafird, A. Vallribera, Green Chem. 2010, 12, 150-158.
39. C. L. Deng, S. M. Guo, Y. X. Xie, J. H. Li, Eur. J. Org. Chem. 2007, 1457-1462
40. I. D. Kostas, B. R. Steele, A. Terzis, S. V. Amosova, A. V. Martynov, N. A. Makhaeva, Eur. J. Inorg. Chem. 2006, 2642-2646
41. Q. Luo, S. Eibauer, O. Reiser, J. Mol. Catal. A: Chem. 2007, 268, 65-69
42. I. D. Kostas, F. J. Andreadaki, D. Kovala-Demertzi, C. Prentjas, M. A. Demertzis, Tetrahedron Lett. 2005, 46, 1967-1970
43. T. Mino, Y. Shirae, M. Sakamoto, T. Fujita, J. Org. Chem. 2005, 70, 2191-2194
44. A. Corma, H. Garcia, A. Leyva, J. Catal. 2006, 240, 87-99.
45. G. W. Gray, M. Hird, K. J. Toyne, Mol. Cryst. Liq. Cryst. 1991, 195, 221-237
46. F. Lincker, P. Bourgun, P. Masson, P. Dider, L. Guidoni, J.-Y. Bigot, J.-F. Nicoud, B. Donnio, D. Guillon, Org. Lett. 2005, 7, 1505-1508.
47. A. Kraft, A. C. Grimsdale, A. B. Holmes, Angew. Chem. 1998, 110, 416-443
48. Angew. Chem. Int. Ed. 1998, 37, 402-428
49. U. Mitschke, P. Bäuerle, J. Mater. Chem. 2000, 10, 1471-1509
50. S.-C. Lo, P. L. Burn, Chem. Rev. 2007, 107, 1097-1116.
51. D. H. Kim, Y. D. Park, Y. Jang, H. Yang, Y. H. Kim, J. I. Han, D. G. Moon, S. Park, T. Chang, C. Chang, M. Joo, C. Y. Ryu, K. Cho, Adv. Funct. Mater. 2005, 15, 77-82
52. M. Funahashi, F. Zhang, N. Tamaoki, Adv. Mater. 2007, 19, 353-358.
53. J. M. Tour, Chem. Rev. 1996, 96, 537-554
54. C. Wang, A. S. Batsanov, M. R. Bryce, I. Sage, Org. Lett. 2004, 6, 2181-2184
55. A. Blaszczyk, M. Chadim, C. von Hänisch, M. Mayor, Eur. J. Org. Chem. 2006, 3809-3825.
56. A. Hayek, F. Bolze, J.-F. Nicoud, P. L. Baldeck, Y. Mély, Photochem. Photobiol. Sci. 2000, 5, 102-106
57. F. Cherioux, A.-J. Attias, H. Maillotte, Adv. Funct. Mater. 2002, 12, 203-208
58. J. Wang, M. Lu, Y. Pan, Z. Peng, J. Org. Chem. 2002, 67, 7781-7786.
59. J. Pang, E. J.-P. Marcotte, C. Seward, R. S. Brown, S. Wang, Angew. Chem. 2001, 113, 4166-4169
60. Angew. Chem. Int. Ed. 2001, 40, 4042-4045
61. A. de La Hoz, A. Dí'az-Ortiz, J. Elguero, L. J. Martí'nez, A. Moreno, A. Sánchez-Migallõn, Tetrahedron 2001, 57, 4397-4403
62. P. K. Thallapally, R. K. R. Jetti, A. K. Katz, H. L. Carrell, K. Singh, K. Lahiri, S. Kotha, R. Boese, G. R. Desiraju, Angew. Chem. 2004, 116, 1169-1175
63. Angew. Chem. Int. Ed. 2004, 43, 1149-1155.
64. J. Palomero, J. A. Mata, F. González, E. Peris, New. J. Chem. 2002, 26, 291-297
65. S. Achelle, Y. Ramondenc, F. Marsais, N. Plé, Eur. J. Org. Chem. 2008, 3129-3140
66. S. Kotha, D. Kashinath, K. Lahiri, R. B. Sunoj, Eur. J. Org. Chem. 2004, 4003-4013.
67. Q. He, H. Huang, J. Yang, H. Lin, F. Bai, J. Mater. Chem. 2003, 13, 1085-1089.
68. H. Hattori, K.-I. Fujita, T. Muraki, A. Sakaba, Tetrahedron Lett. 2007, 48, 6817-6820
69. W. Chen, P. Li, L. Wang, Tetrahedron 2011, 67, 318-325
70. A. Houdayer, R. Schneider, D. Billaud, J. Ghanbaja, J. Lambert, Appl. Organomet. Chem. 2005, 19, 1239-1248
71. N. Iranpoor, H. Firouzabadi, S. Motevalli, M. Talebi, J. Organomet. Chem. 2012, 708-709, 118-124
72. K. K. Senapati, S. Roy, C. Borgohain, P. Phukan, J. Mol. Catal. A: Chem. 2012, 352, 128-134
73. M. Lakshmi Kantam, K. B. Shiva Kumar, P. Srinivas, B. Sreedhara, Adv. Synth. Catal. 2007, 349, 1141-1149
74. C. B. Putta, S. Ghosh, Adv. Synth. Catal. 2011, 353, 1889-1896.
75. V. Polshettiwar, P. Hesemann, J. J. E. Moreau, Tetrahedron Lett. 2007, 48, 5363-5366
76. T. Rama Krishna, N. Jayaraman, Tetrahedron 2004, 60, 10325-10334
77. Y. He, C. Cai, Appl. Organomet. Chem. 2011, 25, 799-803
78. C. M. Crudden, M. Sateesh, R. Lewis, J. Am. Chem. Soc. 2005, 127, 10045-10050
79. J. D. Senra, L. F. B. Malta, A. L. F. Souza, L. C. S. Aguiar, O. A. C. Antunes, Adv. Synth. Catal. 2008, 350, 2551-2558
80. S. Schweizer, J.-M. Becht, C. L. Drian, Adv. Synth. Catal. 2007, 349, 1150-1158
81. P. Li, L. Wang, L. Zhang, G.-W. Wang, Adv. Synth. Catal. 2012, 354, 1307-1318.
82. B. Karimi, A. A. Safari, J. Organomet. Chem. 2008, 693, 2967-2970.