Ethylenediamine-Functionalized Resin-Supported Pd(0) Complex: An Effective and Recyclable Catalyst for Heck Vinylation
Ming Zhuang
Zhejiang Normal University, Jinhua, Zhejiang 321004, China
Search for more papers by this authorChao-Xia Zeng
Institute of Physical Chemistry, Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Zhejiang Normal University, Jinhua, Zhejiang 321004, China
Search for more papers by this authorChao-Biao Huang
Zhejiang Normal University, Jinhua, Zhejiang 321004, China
Search for more papers by this authorMeng-Fei Luo
Institute of Physical Chemistry, Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Zhejiang Normal University, Jinhua, Zhejiang 321004, China
Search for more papers by this authorMing Zhuang
Zhejiang Normal University, Jinhua, Zhejiang 321004, China
Search for more papers by this authorChao-Xia Zeng
Institute of Physical Chemistry, Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Zhejiang Normal University, Jinhua, Zhejiang 321004, China
Search for more papers by this authorChao-Biao Huang
Zhejiang Normal University, Jinhua, Zhejiang 321004, China
Search for more papers by this authorMeng-Fei Luo
Institute of Physical Chemistry, Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Zhejiang Normal University, Jinhua, Zhejiang 321004, China
Search for more papers by this authorAbstract
The ethylenediamine-functionalized resin-supported Pd(0) complex was prepared from PdCl2 and ethylenediamine-functionalized chloromethylated polystyrene, followed by reduction with KBH4. The complex was characterized by FT-IR, XRD, BET, SEM and EDS. The resin-supported catalyst exhibited high catalytic activity in the Heck reaction and could be reused up to 17 times in NMP or 16 times in DMF at 90 °C in the Heck reaction of iodobenzene with acrylic acid. The leaching investigation disclosed that the palladium leaching was caused by the interaction of iodobenzene with the metal Pd(0) on supported catalyst. The leached palladium species in filtrate was very stable and could be reused five times after the solid catalyst was filtered off. A cross-transfer test in recycling in the presence of additional carbon disclosed that the soluble leached palladium species had much higher catalytic activity than supported and/or adsorbed palladium in solid-solution heterogeneous Heck reaction.
REFERENCES
- 1a Beletskaya, I. P.; Cheprakov, A. V.. Chem. Rev., 2000, 100, 3009.
- 1b Biffis, A.; Zecca, M.; Basato, M.. J. Mol. Catal. A: Chem., 2001, 173, 249.
- 2a Clapham, B.; Reger, T. S.; Janda, K. D.. Tetrahedron, 2001, 57, 4637.
- 2b Venkatesan, C.; Singh, A. P.. J. Catal., 2004, 227, 148.
- 2c Viton, F.; White, P. S.; Gagne, M. R.. Chem. Commun., 2003, 3040.
- 3a Nejjar, A.; Pinel, C.; Djakovitch, L.. Synth. Adv. Catal., 2003, 345, 612.
- 3b Heidenreich, R. G.; Krauter, J. G. E.; Pietsch, J.; Köhler, K.. J. Mol. Catal. A: Chem., 2002, 182–183, 499.
- 3c Walter, J.; Heiermann, J.; Dyker, G.; Hara, S.; Shioyama, H.. J. Catal., 2000, 189, 449.
- 4 Mehnert, C. P.; Ying, J. Y.. Chem. Commun., 1997, 2215.
- 5a Mehnert, C. P.; Weaverr, D. W.; Ying, J. Y.. J. Am. Chem. Soc., 1998, 120, 12289.
- 5b Djakovitch, L.; Wagner, M.; Hartung, C. G.; Beller, M.; Koehler, K.. J. Mol. Catal. A: Chem., 2004, 219, 121.
- 6 Tonks, L.; Anson, M. S.; Hellgardt, K.; Mirza, A. R.; Thompson, D. F.; Williams, J. M. J.. Tetrahedron Lett., 1997, 38, 4319.
- 7a Djakovitch, L.; Koehler, K.. J. Mol. Catal. A: Chem., 1999, 142, 275.
- 7b Dams, M.; Drijkoningen, L.; Pauwels, B.; Tendeloo, G. V.; Vos, D. E. D.; Jacobs, P. A.. J. Catal., 2002, 209, 225.
- 8 Köhler, K.; Wagner, M.; Djakovitch, L.. Catalysis Today, 2001, 66, 105.
- 9 Papp, A.; Miklós, K.; Forgo, P.; Molnár, Á.. J. Mol. Catal. A: Chem., 2005, 229, 107.
- 10 de Vries, A. H. M.; Parlevliet, F. J.; de Vondervoort, L. S.-V.; Mommers, J. H. M.; Henderickx, H. J. W.; Walet, M. A. M.; de Vries, J. G.. Adv. Synth. Catal., 2002, 334, 996.
- 11a Yi, P.; Zhang, Z. Y.; Hu, H. W.. J. Mol. Catal., 1990, 62, 297.
- 11b Macquarrie, D. J.; Gotov, B.; Toma, S.. Plat. Met. Rev., 2001, 45, 102.
- 11c Lagasi, M.; Moggi, P.. J. Mol. Catal. A: Chem., 2002, 182–183, 61.
- 11d Steel, P. G.; Teasdale, C. W. T.. Tetrahedron Lett., 2004, 45, 8977.
- 11e Cui, Y. C.; Zhang, L.. J. Mol. Catal. A: Chem., 2005, 237, 120.
- 11f Zhang, L.; Cui, Y. C.. Acta Chim. Sinica, 2005, 63, 924 (in Chinese).
- 11g Liu, P.; Wang, L.; Li, L.-M.; Wang, X. Y.. Chin. J. Org. Chem., 2004, 24, 59 (in Chinese).
- 11h Zhou, J. M.; Zhou, R. X.; Mo, L. Y.; Zhao, S. F.; Zheng, X. M.. Chin. J. Chem., 2001, 19, 987.
- 12 Phan, N. T. S.; Brown, D. H.; Adams, H.; Spey, S. E.; Styring, P.. Dalton Trans., 2004, 1348.
- 13The chloromethyl polystyrene resin support palladium catalyst for Suzuki coupling, see:
- 13a Phan, N. T. S.; Brown, D. H.; Styring, P.. Tetrahedron Lett., 2004, 45, 7915.
- 13b Byun, J. W.; Lee, Y. S.. Tetrahedron Lett., 2004, 45, 1837.
- 13c Fenger, I.; Drian, C. L.. Tetrahedron Lett., 1998, 39, 4287.
- 13d Other supported palladium catalysts For Suzuki cross-coupling reaction, see: (d) Vassylyev, O.; Chen, J.; Panarello, A. P.; Khinast, J. G. Tetrahedron Lett. 2005, 46, 6865.
- 13e Shimizu, K.; Koizumi, S.; Hatamachi, T.; Yoshida, H.; Komai, S.; Kodama, T.; Kitayama, Y.. J. Catal., 2004, 228, 141.
- 14a Yang, Y. F.; Zhou, R. X.; Zhao, S. F.; Li, Q.; Zheng, X. M.. J. Mol. Catal. A: Chem., 2003, 192, 303.
- 14b Zhao, S. F.; Zhou, R. X.; Yang, Y. F.; Zheng, X. M.. Indian J. Chem., 2002, 41A, 2274.
- 15 Zhao, F.; Murakami, K.; Shirai, M.; Arai, M.. J. Catal., 2000, 194, 479.
- 16 Reetz, M. T.; Lohmer, G.. Chem. Commun., 1996, 1921.
- 17 Li, L.; Zhang, L. X.; Shi, J. L.; Yan, J. N.; Liang, J.. Appl. Catal. A: General, 2005, 283, 85.
- 18 Zhao, F.; Shirai, M.; Ikushima, Y.; Arai, M.. J. Mol. Catal. A: Chem., 2002, 180, 211.
- 19 Sheldon, R. A.; Wallau, M.; Arends, I. W. C. E.; Schuchardt, U.. Acc. Chem. Res., 1998, 31, 485.
- 20 Yu, K. Q.; Sommer, W.; Weck, M.; Jones, C. W.. J. Catal., 2004, 226, 101.
- 21a Djakovitch, L.; Koehler, K.. J. Am. Chem. Soc., 2001, 123, 5990.
- 21b Biffis, A.; Zecca, M.; Basato, M.. Eur. J. Inorg. Chem., 2001, 1131.
- 22 Shmidt, A. F.; Mametova, L. V.. Kinet. Catal., 1996, 37, 406.
