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Fiber-Palladium Complex as Highly Active and Recyclable Catalyst for Heck Reaction in Air
Corresponding Author(s) : Tingxian Tao
Asian Journal of Chemistry,
Vol. 25 No. 10 (2013): Vol 25 Issue 10
Abstract
A new amidoxime fibers-palladium catalyst was synthesized by the "coordination-reduction" reaction between the amidoxime groups in fibers and Pd(II) ions. The morphology, structure and composition of the as-obtained complexes were characterized by X-ray diffraction and X-ray photoelectron spectroscopy. The results indicated that the Pd(II) ions were reduced to Pd(0) nanospheres in situ with the diameter of about 100 nm and there were coordination interactions between the Pd nanoparticles and the amidoxime fibers. The prepared catalyst demonstrated high activities for Heck coupling reaction of aryl iodine. During the reaction, the fibers serve as both the ligand and the support. In all cases, the coupling reactions proceeded efficiently without inert atmosphere. The catalyst can be easily recycled for at least eight times.
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- R.F. Heck, Org. React., 27, 345 (1982).
- V. Calo, A. Nacci, A. Monopoli and P. Cotugno, Angew. Chem. Int. Ed., 48, 6101 (2009).
- Q. Du, W. Zhang, H. Ma, J. Zheng, B. Zhou and Y. Li, Tetrahedron, 68, 3577 (2012).
- I.P. Beletskaya and A.V. Cheprakov, J. Organomet. Chem., 689, 4055 (2004).
- Y. Ben-David, M. Portnoy and D. Milstein, J. Am. Chem. Soc., 111, 8742 (1989).
- R.J. Perry and B.D. Wilson, Organometallics, 13, 3346 (1994).
- T. Okano, N. Harada and J. Kiji, J. Bull. Chem. Soc. Jpn, 67, 2329 (1994).
- J.K. Stille, Pure Appl. Chem., 57, 1771 (1985).
- J.G. De Vries, Can. J. Chem., 79, 1086 (2001).
- A. Bianco, C. Cavarischia and M. Guiso, Eur. J. Org. Chem., 13, 2894 (2004).
- J. Zou, K.S. Iyer, S.G. Stewart and C.L. Raston, New J. Chem., 35, 854 (2011).
- Z. Du, W. Zhou, L. Bai, F. Wang and J.X. Wang, Synlett., 369 (2011).
- L. Liu, M.W. Shao and X.H. Wang, Asian J. Chem., 23, 3059 (2011).
- A. Khalafi-Nezhad and F. Panahi, Green Chem., 13, 2408 (2011).
- R. Bernini, S. Cacchi, G. Fabrizi, G. Forte, F. Petrucci, A. Prastaro, S. Niembro, A. Shafir and A. Vallribera, Green Chem., 12, 150 (2010).
- P. Nursel, S. Nurettin, A. Pinar and G. Olgun, Polym. Bull., 44, 593 (2000).
- Y. Li, R.X. Liu and B.W. Zhang, J. Anal. Chem., 366, 821 (2000).
- H.E. Ungnade and L.W. Kissinger, J. Org. Chem., 23, 1794 (1958).
- L. Djakovitch and K. Koehler, J. Mol. Catal. A, 142, 275 (1999).
- F. Zhao, B.M. Bhanage, M. Shirai and M. Arai, Chem. Eur. J., 6, 843 (2000).
- W.A. Herrmann, M. Elison, J. Fischer, C. Kocher and G.R.J. Artus, Angew. Chem. Int. Ed., 34, 2371 (1995).
- Y. Jake, L. Wan, A.B. Xia and W.J. Zheng, Tetrahedron Lett., 48, 8843 (2007).
- B. Andrea, Z. Marco and B. Marino, J. Mol. Catal. A, 173, 249 (2001).
References
R.F. Heck, Org. React., 27, 345 (1982).
V. Calo, A. Nacci, A. Monopoli and P. Cotugno, Angew. Chem. Int. Ed., 48, 6101 (2009).
Q. Du, W. Zhang, H. Ma, J. Zheng, B. Zhou and Y. Li, Tetrahedron, 68, 3577 (2012).
I.P. Beletskaya and A.V. Cheprakov, J. Organomet. Chem., 689, 4055 (2004).
Y. Ben-David, M. Portnoy and D. Milstein, J. Am. Chem. Soc., 111, 8742 (1989).
R.J. Perry and B.D. Wilson, Organometallics, 13, 3346 (1994).
T. Okano, N. Harada and J. Kiji, J. Bull. Chem. Soc. Jpn, 67, 2329 (1994).
J.K. Stille, Pure Appl. Chem., 57, 1771 (1985).
J.G. De Vries, Can. J. Chem., 79, 1086 (2001).
A. Bianco, C. Cavarischia and M. Guiso, Eur. J. Org. Chem., 13, 2894 (2004).
J. Zou, K.S. Iyer, S.G. Stewart and C.L. Raston, New J. Chem., 35, 854 (2011).
Z. Du, W. Zhou, L. Bai, F. Wang and J.X. Wang, Synlett., 369 (2011).
L. Liu, M.W. Shao and X.H. Wang, Asian J. Chem., 23, 3059 (2011).
A. Khalafi-Nezhad and F. Panahi, Green Chem., 13, 2408 (2011).
R. Bernini, S. Cacchi, G. Fabrizi, G. Forte, F. Petrucci, A. Prastaro, S. Niembro, A. Shafir and A. Vallribera, Green Chem., 12, 150 (2010).
P. Nursel, S. Nurettin, A. Pinar and G. Olgun, Polym. Bull., 44, 593 (2000).
Y. Li, R.X. Liu and B.W. Zhang, J. Anal. Chem., 366, 821 (2000).
H.E. Ungnade and L.W. Kissinger, J. Org. Chem., 23, 1794 (1958).
L. Djakovitch and K. Koehler, J. Mol. Catal. A, 142, 275 (1999).
F. Zhao, B.M. Bhanage, M. Shirai and M. Arai, Chem. Eur. J., 6, 843 (2000).
W.A. Herrmann, M. Elison, J. Fischer, C. Kocher and G.R.J. Artus, Angew. Chem. Int. Ed., 34, 2371 (1995).
Y. Jake, L. Wan, A.B. Xia and W.J. Zheng, Tetrahedron Lett., 48, 8843 (2007).
B. Andrea, Z. Marco and B. Marino, J. Mol. Catal. A, 173, 249 (2001).