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首页> 外文期刊>Chemistry: A European journal >Unusual Coupling Reactions of Aldehydes and Alkynes: A Novel Preparation of Substituted Phthalic Acid Derivatives by Automated Synthesis
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Unusual Coupling Reactions of Aldehydes and Alkynes: A Novel Preparation of Substituted Phthalic Acid Derivatives by Automated Synthesis

机译：醛与炔烃的异常偶联反应：通过自动合成方法制备取代的邻苯二甲酸衍生物的新方法

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摘要

Based upon a highly versatile multicomponent methodology, a new one-pot synthesis of substituted phthalic acid derivatives from alpha, beta-unsaturated aldehydes was developed. The reaction invovles the intermediacy of an acetamidodiene species which undergoes Diels-Alder addtion to diethyl acetylenedicarboxylate. The resultant acetamidocyclohexadiene is subject to elimination of acetamide under the reaction conditions to give rise to substituted diethyl phthalates in good yields. This domino condensation-ccyloaddition-elimination sequence has been applied to a variet of alpha,beta-unsaturated aldehydes. Furthermore, we demonstrated the exploitation of paralleized and automated synthesis technology for the rapid screening of reaction conditions and compositions. Detailed studies revealed the catalytic role of the employed acetamide and the occurrence of a sterreoselective 1,4-syn elimination pathway under standard conditions.
机译：基于高度通用的多组分方法，开发了一种新的由一锅合成的由α，β-不饱和醛取代的邻苯二甲酸衍生物的方法。该反应涉及乙酰胺二烯物质的中间体，该乙酰胺二烯物质经过乙炔-二羧酸二乙酯的狄尔斯-阿尔德加成反应。在反应条件下，将所得的乙酰氨基环己二烯除去乙酰胺，以高收率得到取代的邻苯二甲酸二乙酯。该多米诺缩合-Cyloaddition-消除序列已应用于各种α，β-不饱和醛。此外，我们展示了并行和自动化合成技术的开发，用于快速筛选反应条件和组成。详细的研究揭示了所用乙酰胺的催化作用以及在标准条件下发生的立体选择性1,4-syn消除途径。

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