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Synthesis 2019; 51(17): 3221-3230
DOI: 10.1055/s-0037-1611835
DOI: 10.1055/s-0037-1611835
paper
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
We are grateful to the National Natural Science Foundation of China (No. 21372099) for financial support.Further Information
Publication History
Received: 13 March 2019
Accepted after revision: 25 April 2019
Publication Date:
27 May 2019 (online)
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.
Key words
PdII/CeIV/BiIII trimetallic system - imidazole - decarboxylation - Wacker-type oxidation - Debus–Radziszewski reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611835.
- Supporting Information
- CIF File
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