Visible Light-Induced and Singlet Oxygen-Mediated Photochemical Conversion of 4-Hydroxy-α-benzopyrones to 2-Hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxamides/carboxylates Using Rose Bengal as a Photosensitizer.,The Journal of Organic Chemistry

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Visible Light-Induced and Singlet Oxygen-Mediated Photochemical Conversion of 4-Hydroxy-α-benzopyrones to 2-Hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxamides/carboxylates Using Rose Bengal as a Photosensitizer.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-06-16 , DOI: 10.1021/acs.joc.0c00726
Goutam Brahmachari ₁ , Indrajit Karmakar ₁

Affiliation

Development of a visible light-induced and singlet oxygen-mediated green protocol has been accomplished for the first time for the photochemical transformation of 4-hydroxy-α-benzopyrones to a new series of biorelevant 2-hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxamides and 2-hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxylates using rose bengal as a triplet photosensitizer at ambient temperature. Metal-free one-pot synthesis, broader substrate scope, good-to-excellent yields, use of cost-effective and eco-friendly starting materials and photosensitizer, and energy efficiency are the salient features of this newly developed method.

中文翻译：

使用玫瑰红作为光敏剂，将可见的光诱导和单重态氧介导的4-羟基-α-苯并吡喃酮光化学转化为2-羟基-3-氧代-2,3-二氢苯并呋喃-2-羧酰胺/羧酸酯。

首次完成了可见光诱导和单线态氧介导的绿色协议的开发，用于将4-羟基-α-苯并吡喃酮进行光化学转化为一系列新的生物相关的2-羟基-3-氧代-2,3。在室温下，使用玫瑰红作为三重态光敏剂，将-二氢苯并呋喃-2-羧酰胺和2-羟基-3-氧代-2,3-二氢苯并呋喃-2-羧酸酯。这种新开发的方法的主要特点是无金属一锅法合成，更广泛的底物范围，良好至优异的产率，使用经济高效且环保的原料和光敏剂以及能源效率。

更新日期：2020-07-17

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