Synthesis of MCM-41 supported amino-palladium complex and its catalytic performance for heck reaction

Abstract

Using MCM-41 as the supporter, a series of MCM-41 supported amino-palladium complexes has been prepared and characterized by XRD (X-ray diffraction) and XPS (X-ray photoelectron spectroscopy), etc. The XRD and XPS results indicate that the Pd coordinates with the -NH₂ groups on the MCM-41 surface, and the structure of MCM-41 has been not damaged. Its catalytic performance for Heck arylation of alkene with aryl iodide shows that the catalysts have high activity and stereoselectivity in 70-90°C. The product of Heck reaction is in E form. And the effect of the preparation condition of catalyst on the catalytic performance was examined.

Keywords

MCM-41 / palladium complex / heterogeneous catalyst / Heck reaction

References

[1] Heck R F. Palladium-catalysed vinylation of organic halides. Org React, 1982, 27: 345

[2] Jang S B. Polymer-bound palladium-catalyzed coupling of allylic alcohols with hypervalent iodoniumsalts. Tetrahed Lett, 1997, 38(25): 4421-4424

[3] Bergbreiter D E, Osburn P L, Frels J D. Nonpolar Polymers for Metal Sequestration and Ligand and Catalyst Recovery in Thermomorphic Systems. J Am Chem Soc, 2001, 123: 11105-11106

[4] Köhler K, Heidenreich R G, Pietsch J. Highly active palladium/Activated carbon catalysts for Heck reactions: correlation of activity, catalyst properties, and pd leaching. Chem Eur J, 2002, 8(3): 622-631

[5] Cai M Z, Song C S. Synthesis of poly-γ-mercaptopropylsiloxane palladium(0) complex and its catalytic properties. Chem J Chin Univ, 1998, 19(10): 1693-1696 (in Chinese)

[6] Cai M Z, Zhao H, Huang Y Z. Synthesis of Poly-4-oxa-6,7-dimethylselenoheptylsiloxane Palladium(0) Complex and Its Catalytic Properties. Chin J Org Chem, 2003, 23(6): 555-558 (in Chinese)

[7] Köhler K, Magner W, Djakovitch L. Supported palladium as catalyst for carbon-carbon bond construction (Heck reaction) in organic synthesis Catal. Today, 2001, 66(1): 105-114

[8] Mehert C P, Weaver D W, Ying J Y. Heterogeneous Heck catalysis with palladium-grafted molecular sieves. J Am Chem Soc, 1998, 120: 12289-12296

[9] Zhou J M, Zhou R X, Mo L Y, Zhao S F, Zheng X M. MCM-41 supported aminopropylsiloxane palladium acetate complex: A highly active and stereoselective catalyst for Heck reaction. Chin J Chem, 2001, 19: 987-990

[10] Zhou J M, Zhou R X, Mo L Y, Zhao S F, Zheng X M. MCM-41 supported aminopropylsiloxane palladium (0) complex:a highly active and stereoselective catalyst for Heck reaction. J Mol Catal A Chem, 2002, 178 (1): 289-292

[11] Liu P, Wang L, Li L M, Wang X Y. Study on the neck arylation reaction catalyzed by Chitosan-immobilized palladium(0) complex. Chin J Org Chem, 2004, 24(1): 59 (in Chinese)

[12] Luo F T, Xue C, Ko S L. Preparation of polystyrene-supported soluble palladacycle catalyst for Heck and Suzuki reactions. Tetrahed Lett, 2005, 61: 6040-6045

[13] Xie Y X, Li J H, Yin D L. Amines as the ligands for Palladium-catalyzed coupling reaction. Chinese Journal of Organic Chemistry, 2006, 26(8): 1155-1163 (in Chinese)

[14] Beck J S, Vartuli J C, Roth W J. A new family of mesoporous molecular sieves prepared with liquid crystal templating. J Am Chem Soc, 1992, 114: 10834-10843

[15] Zhao F Y, Murakami K, Shirai M, Arai M. Recyclable homogeneous/heterogeneous catalytic systems for Heck reaction through reversible transfer of palladium species between solvent and support. J Catal, 2000, 194: 479

Acknowledgements

We thank the financial support of the Natural Science Foundation of Zhejiang Province of China.

RIGHTS & PERMISSIONS

2014 Higher Education Press and Springer-Verlag Berlin Heidelberg