Synthesize, characterization and application of phosphine-free polymer supported palladium nanoparticles as effective catalyst in Suzuki-Miyaura cross-coupling reactions

Journal of the Chinese Chemical Society

Volumn 60, Issue 4, 2013, Pages 425-436

  Mahdavi, Hossein ^a   Hashemi, Payam ^a  

^a UNIVERSITY OF TEHRAN   (Iran)

Author keywords

C C cross coupling; Heterogeneous catalysis; Palladium nanoparticles; Suzuki Miyaura reaction

Indexed keywords

EID: 84878314386     PISSN: 00094536     EISSN: 21926549     Source Type: Journal    
DOI: 10.1002/jccs.201200257     Document Type: Article

References (66)

1. For general reviews on the cross-coupling reactions, see: (a) Diederich, F.; Stang, P. J. Metal-Catalyzed Cross-Coupling Reactions;Wiley-VCH:Weinheim, 1998.
2. Meijere, A. D.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; Wiley-VCH: Weinheim, 2004.
3. (c) Beller, M.; Bolm, C. Transition Metals for Organic Synthesis, 2nd ed.; Wiley- VCH: Weinheim, 2004; Vol. 1.
4. (d) Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2005, 61, 11771.
5. For selected papers on the palladium-catalyzed Suzuki- Miyaura cross-coupling reaction, see: (a) Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 36, 3437.
6. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
7. (c) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
8. (d) Tsuji, J. Palladium Reagents and Catalysts; JohnWiley & Sons, Inc.: New York, 2004.
9. (e) Zhang, T.; Wang, W.; Gu, X.; Shi, M. Organometallics 2008, 27, 753.
10. (f) Saito, B.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 6694.
11. Miyaura, N. Cross-Coupling Reaction; Springer: Berlin, 2002.
12. (a) Larsen, R. D.; King, A. O.; Chen, C. Y.; Corley, E. G.; Foster, B. S.; Roberts, F. E.; Yang, C.; Lieberman, D. R.; Reamer, R. A.; Tschaen, D. M.; Verhoeven, T. R.; Reider, P. J.; Lo, Y. S.; Rossano, L. T.; Brookes, A. S.; Meloni, D.; Moore, J. R.; Arnett, J. F. J. Org. Chem. 1994, 59, 6391.
13. (b) Haber, S.; Cornils, B.; Herrmann, W. A. Aqueous-Phase Organometallic Catalysis; Wiley-VCH: Weinheim, 1998; p 444.
14. (a) Bringmann, G.; Gotz, R.; Keller, P. A.; Walter, R.; Boyd, M. R.; Lang, F.; Garcia, A.; Walsh, J. J.; Tellitu, I.; Bhaskar, K.V.; Kelly, T. R. J. Org. Chem. 1998, 63, 1090.
15. (b) Abu Ali, H.; Dembitsky, V. M.; Srebnik, M. In Contemporary Aspects of Boron: Chemistry and Biological Applications; Abu Ali, H., Eds.; Elsevier: Amsterdam, The Netherlands, 2005; pp 119-298.
16. (c) Carey, J. S.; Laffan, D.; Thomson, C.;Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337.
17. (a) King, A. O.; Yasuda, N. Topics Organomet. Chem. 2004, 6, 218.
18. (b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 4458.
19. (a). Sabat, M.; Johnson, C. R. Org. Lett. 2000, 2, 1089.
20. (b) Molander, G. A.; Petrillo, D. E.; Landzberg, N. R.; Rohanna, J. C.; Biolatto, B. Synlett. 2005, 11, 1763.
21. (a) Poetsch, E. Kontakte (Darmstadt) 1988, 2, 15.
22. (b) Gray, G. W.; Hird, M.; Lacey, D.; Toyne, K. J. Mol. Cryst. Liq. Cryst. 1989, 172, 165.
23. (c) Hird, M.; Gray, G.W.; Toyne, K. J. Mol. Cryst. Liq. Cryst. 1991, 206, 187.
24. (d) Bahl, A.; Grahn, W.; Stadler, S.; Feiner, F.; Bourhill, G.; Brauchle, C.; Reisner, A.; Jones, P. G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1485.
25. (e) Bolm, C.; Hildebrand, J. P.; Muniz, K.; Hermanns, N. Agew. Chem. Int. Ed. 2001, 40, 3284.
26. (f) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire,M. Chem. Rev. 2002, 102, 1359.
27. (g) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
28. (h) Like, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
29. Gupta, K. C.; Sutar, A. K. Coord. Chem. Rev. 2008, 252, 1420.
30. (a) Kong, K. C.; Cheng, C. H. J. Am. Chem. Soc. 1991, 113, 6313.
31. (b) O'Keefe, D. F.; Dannock, M. C.; Marcuccio, S. M. Tetrahedron Lett. 1992, 33, 6679.
32. (c) Morita, D. K.; Stille, J. K.; Norton, J. R. J. Am. Chem. Soc. 1995, 117, 8576.
33. Garrett, C. E.; Prasad, K. Adv. Synth. Catal. 2004, 346, 889.
34. (a) Sheldon, R. A.; Arends, I.; Hanefeld, U. Green Chemistry and Catalysis; Wiley-VCH: Weinheim, 2007.
35. (b) Fan, G. Z.; Zhang, H. J.; Cheng, S. Q.; Ren, Z. D.; Hu, Z. J.;Wang, Z. L. Aust. J. Chem. 2008, 61, 610.
36. (c) Nohair, B.; MacQuarrie, S.; Crudden, C. M.; Kaliaguine, S. J. Phys. Chem. 2008, 112, 6065.
37. (d) Köhler, K.; Heidenreich, R. G.; Soomro, S. S.; Pröckl, S. S. Adv. Synth. Catal. 2008, 350, 2930.
38. (e) Fan, G.; Zou, B.; Cheng, S.; Zheng, L. J. Ind. Eng. Chem. 2010, 16, 220.
39. (f) Shylesh, S.; Thiel, W. R.; Schünemann, V. Angew. Chem. Int. Ed. 2010, 49, 3428.
40. (a) Felpin, F. X.; Ayad, T.;Mitra, S. Eur. J. Org. Chem. 2006, 2679-2690.
41. (b) Guillén, E.; Rico, R.; López-Romero, J. M.; Bedia, J.; Rosas, J. M.; Rodríguez-Mirasol, J.; Cordero, T. Appl. Catal. A: Gen. 2009, 368, 113.
42. Durgun, G.; Aksin, Ö.; Artok, L. J. Mol. Catal. A: Chem. 2007, 278, 189.
43. For selected papers on the metal oxide supported palladium catalysts, see: (a) Kabalka, G. W.; Pagni, R. M.; Hair, C. M. Org. Lett. 1999, 1, 1423.
44. (b) Choudary, B. M.; Mahdi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127.
45. (c) Kantam, M. L.; Roy, S.; Roy, M.; Sreedhar, B.; Choudary, B. M. Adv. Synth. Catal. 2005, 347, 2002.
46. (d) Scott, R.W. J.; Sivadinarayana, C.;Wilson, O. M.; Yan, Z.; Goodman, D. W.; Crooks, R. M. J. Am. Chem. Soc. 2005, 127, 1380.
47. (e) Kudo, D.; Masui, Y.; Onaka, M. Chem. Lett. 2007, 36, 918.
48. (f) Polshettiwar, V.; Lenb, C.; Fihri, A. Coord. Chem. Rev. 2009, 253, 2599.
49. Xu, Y.; Zhang, L.; Cui, Y. J. Appl. Polym. Sci. 2008, 110, 2996.
50. (a) Hardy, J. J. E.; Hubert, S.; Macquarrie, D. J.; Wilson, A. J. Green Chem. 2004, 6, 53.
51. (b) Guibal, E. Prog. Polym. Sci. 2005, 30, 71.
52. Nakao, R.; Rhee, H.; Uozumi, Y. Org. Lett. 2005, 7, 163.
53. For reviews, see: (a) Heerbeek, R. V.; Kamer, P. C. J.; Leeuwen, P. W. N. M. V.; Reek, J. N. H. Chem. Rev. 2002, 102, 3717.
54. (b) Reek, J. N. H.; Arévalo, S.; van Heerbeek, R.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Adv. Catal. 2006, 49, 71.
55. (a) Lu, J.; Toy, P. H. Chem. Rev. 2009, 109, 815.
56. (b) Schweizer, S.; Becht, J. M.; Le Drian, C. Tetrahedron 2010, 66, 765.
57. Astruc, D. Nanoparticles and Catalysis; Wiley-VCH: Weinheim, 2008; Vol. 1.
58. (a) Astruc, D. Inorg. Chem. 2007, 46, 1884.
59. (b) Molnár, Á. Chem. Rev. 2011, 111, 2251.
60. Moreno-Maas, M.; Pleixats, R. Acc. Chem. Res. 2003, 36, 638.
61. Tamami, B.; Ghasemi, S. J. Mol. Catal. A: Chem. 2010, 322, 98.
62. Mahdavi, H.; Zirakzadeh, A.; Amani, J. React. Funct. Polym. 2007, 67, 716.
63. Hausman, E. A.; Grasso, J. R.; Pond, G. US Pat. No. 3318891, 1967.
64. (a) Toebes, M. L.; van Dillen, J. A.; de Jong, K. P. J. Mol. Catal. A: Chem. 2001, 173, 75.
65. (b) Zou,W.; Gonzalez, R. D. Appl. Catal. A Gen. 1995, 126, 351.
66. Patterson, A. L. Phys. Rev. 1939, 56, 978.