Synthesis of Imidazolium Precursors for the Hydroxyl-Group-Modified N-Heterocyclic Carbenes and Applications of the in situ Generated Carbene Ligands in Suzuki-Miyaura and Sonogashira Coupling Reactions

doi:10.6023/cjoc201610039

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (5): 1258-1265.DOI: 10.6023/cjoc201610039 Previous Articles Next Articles

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含羟基氮杂环卡宾的咪唑盐前体的合成及其原位产生的卡宾配体在Suzuki-Miyaura和Sonogashira反应中的应用

白亚丽^a, 李晓维^b, 肖雪冬^a, 刘佳琦^a, 杨俊娟^a, 王君文^a

a 山西师范大学化学与材料科学学院临汾 041000;
b 内蒙古大唐国际再生资源开发有限公司呼和浩特 010000

收稿日期:2016-10-22 修回日期:2016-12-06 发布日期:2017-02-08
通讯作者: 王君文 E-mail:wangjunwen2013@126.com
基金资助:
山西省基础研究计划项目（No.2015011029）、山西师范大学大学生创新实验项目（No.SD2014CXXM-36）及山西省研究生教育创新（No.2015BY38）资助项目.

Synthesis of Imidazolium Precursors for the Hydroxyl-Group-Modified N-Heterocyclic Carbenes and Applications of the in situ Generated Carbene Ligands in Suzuki-Miyaura and Sonogashira Coupling Reactions

Bai Yali^a, Li Xiaowei^b, Xiao Xuedong^a, Liu Jiaqi^a, Yang Junjuan^a, Wang Junwen^a

a Department of Chemistry, Shanxi Normal University, Linfen 041000;
b Inner Mongolia Datang International Renewable Resources Development Co. Ltd., Hohhot 010000

Received:2016-10-22 Revised:2016-12-06 Published:2017-02-08
Contact: 10.6023/cjoc201610039 E-mail:wangjunwen2013@126.com
Supported by:
Project supported by the Basic Research Project of Shanxi Province of China (No. 2015011029), the Undergraduate Innovative Experiment Program of Shanxi Normal University (No. SD2014CXXM-36) and the Shanxi Province Education Innovation Project for Postgraduate (No. 2015BY38).

1. Synthesis of Imidazolium Precursors for the Hydroxyl-Group-Modified N-Heterocyclic Carbenes and Applications of the in situ Generated Carbene Ligands in Suzuki-Miyaura and Sonogashira Coupling Reactions.PDF(817KB)

Abstract

Four imidazolium precursors for the N-heterocyclic carbenes (NHCs) with a hydroxyl functionalized four-mem-bered heterocyclic side arm were synthesized and characterized by IR, XRD and NMR spectroscopies. The corresponding NHC ligands thus generated in situ from these imidazolium precursors in the presence of base such as KOH, together with PdCl₂(CH₃CN)₂, exhibited excellent catalytic activity in Suzuki-Miyaura cross-coupling reactions for the synthesis of a range of biaryl compounds. The reactions could be conducted in the mixed solvent of tert-butyl alcohol/water (V:V=1:1) at room temperature with the advantages of mild conditions, high efficiency as well as environmental friendliness. In addition, although in minor amount, the mixed catalyst system containing imidazolium salts, PdCl₂(CH₃CN)₂ (0.1%) and CuI (1%) exhibited excellent catalytic activity in Sonogashira coupling reaction. In particular, the combination system of PdCl₂/imidazolium salt 3b has been shown to be higher catalytically active for both coupling reactions.

Key words: hydroxyl group, N-heterocyclic carbene, palladium, Suzuki-Miyaura cross-coupling, Sonogashira cross-coupling

Cite this article

Bai Yali, Li Xiaowei, Xiao Xuedong, Liu Jiaqi, Yang Junjuan, Wang Junwen. Synthesis of Imidazolium Precursors for the Hydroxyl-Group-Modified N-Heterocyclic Carbenes and Applications of the in situ Generated Carbene Ligands in Suzuki-Miyaura and Sonogashira Coupling Reactions[J]. Chin. J. Org. Chem., 2017, 37(5): 1258-1265.

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含羟基氮杂环卡宾的咪唑盐前体的合成及其原位产生的卡宾配体在Suzuki-Miyaura和Sonogashira反应中的应用

Synthesis of Imidazolium Precursors for the Hydroxyl-Group-Modified N-Heterocyclic Carbenes and Applications of the in situ Generated Carbene Ligands in Suzuki-Miyaura and Sonogashira Coupling Reactions

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