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4-羟基-α-苯并吡喃酮的电重排双官能化反应

Electrorearranged Difunctionalization of 4-Hydroxy-α-benzopyrones.

作者信息

Karmakar Indrajit, Brahmachari Goutam

机构信息

Laboratory of Natural Products & Organic Synthesis, Department of Chemistry, Visva-Bharati (a Central University), Santiniketan-731 235, West Bengal, India.

出版信息

J Org Chem. 2024 Aug 2;89(15):10524-10537. doi: 10.1021/acs.joc.4c00734. Epub 2024 Jul 19.

Abstract

We herein report the exploration of an electrosynthetic strategy as a highly efficient and straightforward alternative protocol for accessing diversely substituted and biologically promising alkyl 2-hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxylates through an electrorearranged difunctionalization of 4-hydroxycoumarins, involving the singlet oxygen insertion from molecular oxygen, at ambient temperature. The present method is notably more advantageous than the previously reported photochemical conversion regarding yields and reaction times, substrate scope and functional group tolerability, operational simplicity, and scalability.

摘要

我们在此报告了一种电合成策略的探索,该策略是一种高效且直接的替代方案,可通过4-羟基香豆素的电重排双官能团化反应,在室温下利用分子氧插入单线态氧,获得具有不同取代基且具有生物学前景的2-羟基-3-氧代-2,3-二氢苯并呋喃-2-羧酸烷基酯。就产率、反应时间、底物范围和官能团耐受性、操作简便性和可扩展性而言,本方法明显优于先前报道的光化学转化方法。

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