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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 04: 820 - 826

DOI: https://doi.org/10.6023/cjoc201301077

Articles

Montmorillonite Supported Pd/Cu Bimetallic Nanoparticle Catalyzed Sonogashira Coupling

  • Xu Wei ,
  • Sun Yuanlong ,
  • Guo Menghan ,
  • Zhang Weiqiang ,
  • Gao Ziwei
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  • School of Chemisty & Chemical Engineering, Shaanxi Normal University, Xi'an 710062

Received date: 2013-01-29

  Revised date: 2013-03-18

  Online published: 2013-03-22

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21271124, 21041004, 20771071), the Program for New Century Excellent Talents in University (No. NCET-07-0528), the Fundamental Research Funds for the Central Universities (Nos. GK201002031, GK201004010) and the Doctoral Fund of Ministry of Education of China (No. 20120202120005).

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Abstract

To demonstrate the bimetallic effect of transition metal catalyzed C—C cross coupling, the montmorillonite (MMT) supported mixed palladium and copper nanoparticles were prepared and applied to catalytic Sonogashira couplings. A new method of preparing mixed metal nanoparticles was invented based on unique metal ion adsorption capacity of montmorillonite and sequential reductive carbonylation via thermolysis of N,N-dimethylformide, and Pd/Cu bimetallic nanoparticals was prepared in the ratio of 1∶1. A mixed solvent system, dimethoxyethane/water (V∶V＝1∶4) was identified as the best solvent of the catalytic coupling. MMT@Pd/Cu catalyzed efficiently the cross-coupling of aryl iodides and terminal aryl- and alkyl-ynes in presence of potassium carbonate and triphenyl phosphine. 15 cross-coupling yne derivatives were isolated in excellent to moderate yields. Experimental kinetic study reveals that both swelling of montmorillonite promoted by water and Pd/Cu bimetallic synergistic effect play critical roles in high activity of the catalyst.

Key words： transition metal catalysis; montmorillonite; C—C cross-coupling; bimetallic effect

Cite this article

Xu Wei , Sun Yuanlong , Guo Menghan , Zhang Weiqiang , Gao Ziwei . Montmorillonite Supported Pd/Cu Bimetallic Nanoparticle Catalyzed Sonogashira Coupling[J]. Chinese Journal of Organic Chemistry, 2013 , 33(04) : 820 -826 . DOI: 10.6023/cjoc201301077

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