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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 11: 3747 - 3756

DOI: https://doi.org/10.6023/cjoc202206005

ARTICLES

Amide Functionalized Pyridine/Pyrimidine Chelating N-Heterocyclic Carbene Palladium Complexes: Synthesis, Structure, and Catalysis for C-5 Arylation of Imidazoles

  • Xianghui Meng ,
  • Liangru Yang ,
  • Qilin Liu ,
  • Zhenhua Dong ,
  • Jinwei Yuan ,
  • Yongmei Xiao ,
  • Pu Mao
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  • School of Chemistry & Chemical Engineering, Henan University of Technology, Zhengzhou 450001
*E-mail: ;
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Received date: 2022-06-03

  Revised date: 2022-07-08

  Online published: 2022-07-21

Supported by

Natural Science Foundation of Department of Science and Technology of Henan Province(212102310332); Merit Funding for the Oversea Staff of Henan Province; Fundamental Research Funds for the Henan Provincial Colleges and Universities in Henan University of Technology(2017RCJH08); Innovative Funds Plan of Henan University of Technology(2020ZKCJ29)

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Abstract

A series of N-alkylamide-N'-pyridine/pyrimidine di-functionalized imidazolium salts were synthesized using amino acids as starting material. The following direction metallation with Pd(OAc)2 in CH2Cl2 at room temperature produced chelating N-heterocyclic carbene (NHC) palladium complexes with pyridine/pyrimidine coordinated. The structures have been characterized by nuclear magnetic resonance (NMR), mass spectrum (MS) or elemental analysis (EA). The molecular strucuture of pyridine chelating NHC palladium complex 5c has been further characterized unambiguously by X-ray single crystal analysis. Catalytic activity exploration of the complexes demonstrated their high efficiency towards the C-5 arylation of imidazole derivatives in dimethylacetamide (DMAc) with KOAc as base.

Key words： N-heterocyclic carbene; chelating; palladium complex; arylation of imidazoles

Cite this article

Xianghui Meng , Liangru Yang , Qilin Liu , Zhenhua Dong , Jinwei Yuan , Yongmei Xiao , Pu Mao . Amide Functionalized Pyridine/Pyrimidine Chelating N-Heterocyclic Carbene Palladium Complexes: Synthesis, Structure, and Catalysis for C-5 Arylation of Imidazoles[J]. Chinese Journal of Organic Chemistry, 2022 , 42(11) : 3747 -3756 . DOI: 10.6023/cjoc202206005

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