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Heck Arylation of Conjugated Alkenes with Aryl Bromides or Chlorides Catalyzed by Immobilization of Palladium in MCM-41

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Abstract

A new 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized palladium(II) complex [MCM-41-2N-PdCl2] was conveniently synthesized from commercially available and cheap 3-(2-aminoethylamino)propyltrimethoxysilane via immobilization on MCM-41, followed by reacting with palladium chloride. It was found that this heterogeneous palladium complex is a highly efficient catalyst for Heck arylation of conjugated alkenes with aryl bromides or chlorides using tetrabutylammonium bromide as additive and can be reused for at least six consecutive trials without any decreases in activity.

Graphical Abstract

Heck arylation of conjugated alkenes with aryl bromides or chlorides by using 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized palladium(II) complex [MCM-41-2N-PdCl2] as an efficient heterogeneous catalyst with TBAB as additive is described. This heterogeneous palladium complex is highly active catalyst and can be reused at least six times without any decrease in activity.

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Acknowledgments

We gratefully acknowledge the financial support of this work by the National Natural Science Foundation of China (Project No. 20862008) and the Natural Science Foundation of Jiangxi Province in China (Project No. 2010GZH0062).

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Authors and Affiliations

  1. Department of Chemistry, Jiangxi Normal University, Nanchang, 330022, People’s Republic of China

    Fang Yao, Jiaqin Liu & Mingzhong Cai

  2. Department of Chemistry and Pharmaceutical Engineering, West Branch of Zhejiang University of Technology, Quzhou, 324000, People’s Republic of China

    Fang Yao

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  1. Fang Yao
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  2. Jiaqin Liu
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Correspondence to Mingzhong Cai.

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Yao, F., Liu, J. & Cai, M. Heck Arylation of Conjugated Alkenes with Aryl Bromides or Chlorides Catalyzed by Immobilization of Palladium in MCM-41. Catal Lett 143, 681–686 (2013). https://doi.org/10.1007/s10562-013-1013-7

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  • DOI: https://doi.org/10.1007/s10562-013-1013-7

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