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Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 8: 2953 - 2960

DOI: https://doi.org/10.6023/cjoc202301016

Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes

  • Changjun Liu ,
  • Huiling Hu ,
  • Chenghong Liu ,
  • Chaojie Zhu ,
  • Tiandi Tang
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  • a School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164
    b School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189
*E-mail: ;

Received date: 2023-01-17

  Revised date: 2023-03-03

  Online published: 2023-03-31

Supported by

The National Natural Science Foundation of China(21776022); The National Natural Science Foundation of China(22178029)

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Abstract

The 1,2-dione compounds was synthesized under clean reaction conditions over Pd/METS-10 catalyst. It has been found that the key step of the protocol is forming an electron donor-acceptor complex (EDX), as the coordination of Pd(II) and alkynyl. Then the nucleophilic addition and elimination reactions of dimethyl sulfoxide (DMSO) to the EDX were occurred, affording the target product. Pd/METS-10 catalyzed endo-acetylene oxidation possesses excellent product selectivity and good substrate scope. It is compatible with both symmetric and asymmetric endo-acetylene and is insensitive to the electronic properties and stereoscopic effects of the substrate. In addition, Pd/METS-10 catalyst showed excellent repetition performance in the reaction, with no significant loss of activity after five cycles. Finally, according to the characterization and control experiment results, the reaction mechanism of Pd/METS-10 catalyzed acetylene oxidation to produce 1,2-dione was proposed.

Key words： Pd/METS-10; internal alkyne; 1,2-diketone compound; electron donor-acceptor complex; oxidation reaction

Cite this article

Changjun Liu , Huiling Hu , Chenghong Liu , Chaojie Zhu , Tiandi Tang . Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes[J]. Chinese Journal of Organic Chemistry, 2023 , 43(8) : 2953 -2960 . DOI: 10.6023/cjoc202301016

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