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One-Pot Synthesis of Polysubstituted Imidazoles Based on Pd(OAc)2/Ce(SO4)2/Bi(NO3)3 Trimetallic Cascade of Decarboxylation/Wacker-Type Oxidation/Debus–Radziszewski Reaction
Synthesis ( IF 2.2 ) Pub Date : 2019-05-27 , DOI: 10.1055/s-0037-1611835
Wei Sun 1 , Mingjuan Zhang 1 , Peilang Li 1 , Yiqun Li 1, 2
Affiliation  

Abstract

A novel and highly efficient one-pot synthesis of polysubstituted imidazoles from α-hydroxyphenylacetic acids, diphenylacetylene, and amines has been achieved by Pd(OAc)2/Ce(SO4)2/Bi(NO3)3 trimetallic catalytic system. A series of control experiments showed that this overall reaction occurs through a one-pot cascade process combining the steps of decarboxylation of α-hydroxyphenylacetic acids, Wacker-type oxidation of diphenylacetylene, and Debus–Radziszewski annulation of aryl aldehydes and benzil generated in situ, as well as amines. This reaction represents a novel multicomponent reaction using α-hydroxyphenylacetic acids and diphenylacetylene as sources of aryl aldehydes and a β-diketone. This process exhibits a broad substrate scope and a good functional group tolerance to assemble the corresponding polysubstituted imidazoles in excellent yields (72–88%) under mild conditions.

A novel and highly efficient one-pot synthesis of polysubstituted imidazoles from α-hydroxyphenylacetic acids, diphenylacetylene, and amines has been achieved by Pd(OAc)2/Ce(SO4)2/Bi(NO3)3 trimetallic catalytic system. A series of control experiments showed that this overall reaction occurs through a one-pot cascade process combining the steps of decarboxylation of α-hydroxyphenylacetic acids, Wacker-type oxidation of diphenylacetylene, and Debus–Radziszewski annulation of aryl aldehydes and benzil generated in situ, as well as amines. This reaction represents a novel multicomponent reaction using α-hydroxyphenylacetic acids and diphenylacetylene as sources of aryl aldehydes and a β-diketone. This process exhibits a broad substrate scope and a good functional group tolerance to assemble the corresponding polysubstituted imidazoles in excellent yields (72–88%) under mild conditions.



中文翻译:

基于Pd(OAc)2 / Ce(SO4)2 / Bi(NO3)3三金属级联的脱羧/瓦克型氧化/ Debus-Radziszewski反应一锅法合成多取代的咪唑

抽象的

通过Pd(OAc)2 / Ce(SO 42 / Bi(NO 33从α-羟基苯基乙酸,二苯乙炔和胺中合成新颖高效的一锅合成咪唑三金属催化体系。一系列对照实验表明,整个反应是通过一锅级联过程完成的,该过程结合了α-羟基苯基乙酸的脱羧步骤,二苯基乙炔的Wacker型氧化步骤以及原位生成的芳基醛和苯的Debus-Radziszewski环合反应,以及胺。该反应代表使用α-羟基苯基乙酸和二苯乙炔作为芳基醛和β-二酮的来源的新颖的多组分反应。该方法具有宽泛的底物范围和良好的官能团耐受性,可在温和条件下以优异的收率(72–88%)组装相应的多取代的咪唑。

通过Pd(OAc)2 / Ce(SO 42 / Bi(NO 33从α-羟基苯基乙酸,二苯乙炔和胺中合成新颖高效的一锅合成咪唑三金属催化体系。一系列对照实验表明,整个反应是通过一锅级联过程完成的,该过程结合了α-羟基苯基乙酸的脱羧步骤,二苯基乙炔的Wacker型氧化步骤以及原位生成的芳基醛和苯的Debus-Radziszewski环合反应,以及胺。该反应代表使用α-羟基苯基乙酸和二苯乙炔作为芳基醛和β-二酮的来源的新颖的多组分反应。该方法具有宽泛的底物范围和良好的官能团耐受性,可在温和条件下以优异的收率(72–88%)组装相应的多取代的咪唑。

更新日期:2019-05-27
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