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

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

研究论文

酰胺功能化吡啶/嘧啶螯合氮杂环卡宾钯化合物的合成、结构及其催化的咪唑C-5芳基化反应

  • 孟祥辉 ,
  • 杨亮茹 ,
  • 刘琪琳 ,
  • 董振华 ,
  • 袁金伟 ,
  • 肖咏梅 ,
  • 毛璞
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  • 河南工业大学化学化工学院 郑州 450001

收稿日期: 2022-06-03

  修回日期: 2022-07-08

  网络出版日期: 2022-07-21

基金资助

河南省科技厅自然科学基金(212102310332); 河南省留学人员科技活动择优资助; 河南工业大学河南省省属高校基本科研业务费专项基金(2017RCJH08); 河南工业大学创新基金支持计划专项(2020ZKCJ29)

收起

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: ;
;

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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摘要

以氨基酸为原料, 合成了一系列N-烷基酰胺-N'-吡啶/嘧啶双官能团化的咪唑鎓盐, 室温下与Pd(OAc)2在CH2Cl2溶液中经直接金属化反应生成吡啶/嘧啶螯合的氮杂环卡宾钯化合物. 所得化合物的结构经核磁共振(NMR)、质谱(MS)或元素分析(EA)鉴定, 其中吡啶螯合氮杂环卡宾钯化合物5c的结构进一步经X射线单晶衍射确证. 催化活性研究表明, 使用二甲基乙酰胺(DMAc)为溶剂、KOAc为碱时, 这些化合物对咪唑衍生物的C-5芳基化反应表现出很高的催化活性.

关键词： 氮杂环卡宾; 螯合; 钯化合物; 咪唑芳基化反应

本文引用格式

孟祥辉 , 杨亮茹 , 刘琪琳 , 董振华 , 袁金伟 , 肖咏梅 , 毛璞 . 酰胺功能化吡啶/嘧啶螯合氮杂环卡宾钯化合物的合成、结构及其催化的咪唑C-5芳基化反应[J]. 有机化学, 2022 , 42(11) : 3747 -3756 . DOI: 10.6023/cjoc202206005

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

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