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Glucopyranoside-Functionalized NHCs-Pd(II)-PEPPSI Complexes: Anomeric Isomerism Controlled and Catalytic Activity in Aqueous Suzuki Reaction
Catalysis Letters ( IF 2.8 ) Pub Date : 2021-05-25 , DOI: 10.1007/s10562-021-03654-0
Zhonggao Zhou , Qian Xie , Jing Li , Yangyang Yuan , Yong Liu , Yulong Liu , Dongliang Lu , Yongrong Xie

The first system controlled anomeric isomerism of glucopyranoside-functionalized N-heterocyclic carbenes based pyridine enhanced precatalyst preparation, stabilization and initiation type palladium(II) complexes (Glu-NHCs-Pd(II)-PEPPSI, 2a–d) were prepared and fully characterized. It is interesting to note that pure β–anomer PEPPSI complex 2d was obtained, in which the Glu-substituent connects to the imidazole heterocycle ring N through ethoxy bridged anomeric carbon. In addition, the catalytic activities revealed that Glu-NHCs-Pd(II)-PEPPSI complexes 2a-d are efficient catalysts for the aqueous Suzuki reaction. Under optimized conditions, a series of fluorene-cored functional materials with different aryl-substituents were synthesized through the Suzuki reaction with excellent yields. The Glu-NHCs-Pd(II)-PEPPSI complex containing bulky and rigid 2,5-dimethylphenyl group played an important role in maintaining the β conformation and improving the catalytic activity significantly.

Graphic Abstract



中文翻译:

氨基葡萄糖苷功能化的NHCs-Pd(II)-PEPPSI配合物:端粒异构体控制和水催化铃木反应中的催化活性。

制备了吡喃葡萄糖苷官能化的N-杂环卡宾基于吡啶的第一个系统控制的异头异构体,吡啶增强了预催化剂的制备,稳定化和引发型钯(II)配合物(Glu-NHCs-Pd(II)-PEPPSI,2a–d)并进行了充分表征。有趣的是,纯β得到了–anomer PEPPSI配合物2d,其中Glu取代基通过乙氧基桥接的异头碳连接到咪唑杂环N。此外,催化活性表明,Glu-NHCs-Pd(II)-PEPPSI配合物2a-d是水性Suzuki反应的有效催化剂。在最佳条件下,通过铃木反应以优异的收率合成了一系列具有不同芳基取代基的芴核功能材料。含有庞大且刚性的2,5-二甲基苯基的Glu-NHCs-Pd(II)-PEPPSI络合物在维持β构象和显着提高催化活性方面起着重要作用。

图形摘要

更新日期:2021-05-25
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