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以胺作为双功能有机催化剂,通过乙醛酸的电化学脱羧反应合成3-甲酰基吲哚。

Synthesis of 3-Formylindoles via Electrochemical Decarboxylation of Glyoxylic Acid with an Amine as a Dual Function Organocatalyst.

作者信息

Lin Dian-Zhao, Huang Jing-Mei

机构信息

Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering , South China University of Technology , Guangzhou , Guangdong 510640 , China.

出版信息

Org Lett. 2019 Aug 2;21(15):5862-5866. doi: 10.1021/acs.orglett.9b01971. Epub 2019 Jul 16.

DOI:10.1021/acs.orglett.9b01971
PMID:31310138
Abstract

A new method for 3-formalytion of indoles has been developed through electrochemical decarboxylation of glyoxylic acid with the amine as a dual function organocatalyst. The amine facilitated both the electrochemical decarboxylation and the nucleophilic reaction efficiently, whose loading can be as low as 1 mol %. This protocol has a broad range of functional group tolerance under ambient conditions. The gram-scale experiment has shown great potential in the synthetic application of this strategy.

摘要

通过以胺作为双功能有机催化剂对乙醛酸进行电化学脱羧反应,开发了一种吲哚3-甲酰化的新方法。该胺有效地促进了电化学脱羧反应和亲核反应,其负载量可低至1 mol%。该方法在环境条件下对官能团具有广泛的耐受性。克级实验表明了该策略在合成应用中的巨大潜力。

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